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{{About|the chemical compounds alkaloids|the [[pharmaceutical company]] in the [[Republic of Macedonia]]|Alkaloid (company)}}
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[[File:Papaver somniferum 01.jpg|thumb|250px|The first individual alkaloid, [[morphine]], was isolated in 1804 from [[opium poppies|poppy]] (''Papaver somniferum'').<ref>{{cite book|url=http://books.google.com/?id=MtOiLVWBn8cC&pg=PA20|page=20|title=Molecular, clinical and environmental toxicology|author=Andreas Luch|publisher=Springer|year=2009|isbn=3-7643-8335-6}}</ref>]]
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== Paget's 1904 drawing ==
'''Alkaloids''' are a group of naturally occurring [[chemical compound]]s that contain mostly [[base (chemistry)|basic]] [[nitrogen]] atoms. This group also includes some related compounds with neutral<ref name="goldbook.iupac.org">[http://goldbook.iupac.org/A00220.html IUPAC. Compendium of Chemical Terminology], 2nd ed. (The "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997) ISBN 0-9678550-9-8 {{doi|10.1351/goldbook}}</ref> and even weakly [[acid]]ic properties.<ref>R. H. F. Manske. ''The Alkaloids. Chemistry and Physiology''. Volume VIII. – New York: [[Academic Press]], 1965, p. 673</ref> Some synthetic compounds of similar structure are also attributed to alkaloids.<ref>Robert Alan Lewis. [http://books.google.com/books?id=caTqdbD7j4AC&pg=PA51 ''Lewis' dictionary of toxicology'']. CRC Press, 1998, p. 51 ISBN 1-56670-223-2</ref> In addition to [[carbon]], [[hydrogen]] and [[nitrogen]], alkaloids may also contain [[oxygen]], [[sulfur]] and more rarely other elements such as [[chlorine]], [[bromine]], and [[phosphorus]].<ref name="XimE: alkaloidy">[http://www.xumuk.ru/encyklopedia/119.html Chemical Encyclopedia: alkaloids]. xumuk.ru</ref>


Am I alone in looking at this drawing and seeing it as a drawing of Clive Merrison? Either it is amazing how much Clive resembles the drawing or it questions if this is really a 1904 drawing?
Alkaloids are produced by a large variety of organisms, including [[bacteria]], [[fungus|fungi]], [[plant]]s, and [[animal]]s, and are part of the group of [[natural product]]s (also called [[secondary metabolite]]s). Many alkaloids can be purified from crude extracts by [[acid-base extraction]]. Many alkaloids are [[toxicity|toxic]] to other organisms. They often have [[pharmacology|pharmacological]] effects and are used as [[medication]]s, as [[recreational drug]]s, or in [[entheogenic]] rituals. Examples are the [[local anesthetic]] and [[stimulant]] [[cocaine]], the psychedelic [[psilocin]], the stimulant [[caffeine]], [[nicotine]],<ref>{{cite web|title=Alkaloid|url=http://science.howstuffworks.com/alkaloid-info.htm}}</ref> the [[analgesic]] [[morphine]], the antibacterial [[berberine]], the anticancer compound [[vincristine]], the antihypertension agent [[reserpine]], the cholinomimeric [[galantamine]], the spasmolysis agent [[atropine]], the vasodilator [[vincamine]], the anti-arrhythmia compound [[quinidine]], the anti-asthma therapeutic [[ephedrine]], and the [[antimalarial drug]] [[quinine]].
I assume we all know that Clive Merrison has portrayed Holmes on radio more completely than any other actor?  <small><span class="autosigned">— Preceding [[Wikipedia:Signatures|unsigned]] comment added by [[User:PeterM88|PeterM88]] ([[User talk:PeterM88|talk]] • [[Special:Contributions/PeterM88|contribs]]) 07:14, 4 September 2013 (UTC)</span></small><!-- Template:Unsigned --> <!--Autosigned by SineBot-->
Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a [[Bitter (taste)#Bitterness|bitter taste]].<ref name=Rhoades1979>{{cite book|year=1979 |author=Rhoades, David F |chapter=Evolution of Plant Chemical Defense against Herbivores |editor=Rosenthal, Gerald A., and Janzen, Daniel H|title=Herbivores: Their Interaction with Secondary Plant Metabolites |place=New York |publisher=Academic Press |page=41 |isbn=0-12-597180-X}}</ref>
:So Paget not only predicted the future, but he could also see how someone would look on the radio.  Most singularly unique! ;)


== Surname ==
The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.<ref name="Meyers">Robert A. Meyers ''Encyclopedia of Physical Science and Technology'' – Alkaloids, 3rd edition. ISBN 0-12-227411-3</ref> Compounds like [[amino acid]] [[peptide]]s, [[protein]]s, [[nucleotide]]s, [[nucleic acid]], [[amine]]s, and [[antibiotics]] are usually not called alkaloids.<ref name="goldbook.iupac.org"/> Natural compounds containing nitrogen in the [[Alicyclic compound|exocyclic]] position ([[mescaline]], [[serotonin]], [[dopamine]], etc.) are usually attributed to [[amine]]s rather than alkaloids.<ref>Leland J. Cseke [http://books.google.com/books?id=wV2T41nGFc4C&pg=PA30 Natural Products from Plants] Second Edition. – CRC, 2006, p. 30 ISBN 0-8493-2976-0</ref> Some authors, however, consider alkaloids a special case of amines.<ref>A. William Johnson [http://books.google.com/books?id=0X4cQus2gz8C&pg=PA433 Invitation to Organic Chemistry], Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6</ref><ref>Raj K Bansal [http://books.google.com/books?id=1B6ijcTkD5EC&pg=PA644 A Text Book of Organic Chemistry]. 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1</ref><ref name="Aniszewski 110">[[#Aniszewski|Aniszewski]], p. 110</ref>


: [[Talk:Arthur Conan Doyle/Archive 1#Doyle or Conan Doyle?]] (2006–2008)
==Naming==
: [[Talk:Arthur Conan Doyle/Archive 1#Conan Doyle or Doyle?]] (2007–2009)
[[File:Meissner alkalod definition article 1819.png|thumb|160px|The article that introduced the concept of "alkaloid".]]


In effect I continue those two old threads. The rest of this note (including my signature and timestamp) is copied from [[Talk:Adrian Conan Doyle]]. -P64 (22:05)
The name "alkaloids" ({{lang-de|Alkaloide}}) was introduced in 1819 by the German chemist [[:de:Carl Friedrich Wilhelm Meißner|Carl Friedrich Wilhelm Meißner]], and is derived from late Latin root ''{{lang-la|alkali}}'' (which, in turn, comes from the Arabic ''al-qalwī'' – "ashes of plants") and the suffix ''{{lang-el|-οειδής}}'' – "like".<ref group="nb">In the penultimate sentence of his article – W. Meissner (1819) "Über Pflanzenalkalien: II. Über ein neues Pflanzenalkali (Alkaloid)" (On plant alkalis: II. On a new plant alkali (alkaloid)), ''Journal für Chemie und Physik'', '''25''' : 379–381 ; available on-line at:  [http://babel.hathitrust.org/cgi/pt?id=nyp.33433069069056;view=1up;seq=415 Hathi Trust] – Meissner wrote:  "''Überhaupt scheint es mir auch angemessen, die bis jetzt bekannten Pflanzenstoffe nicht mit dem Namen Alkalien, sondern Alkaloide zu belegen, da sie doch in manchen Eigenschaften von den Alkalien sehr abweichen, sie würden daher in dem Abschnitt der Pflanzenchemie vor den Pflanzensäuren ihre Stelle finden''." (In general, it seems appropriate to me to impose on the currently known plant substances not the name "alkalis" but "alkaloids", since they differ greatly in some properties from the alkalis; among the chapters of plant chemistry, they would therefore find their place before plant acids [since "Alkaloid" would precede "Säure" (acid)].)</ref> However, the term came into wide use only after the publication of a review article by Oscar Jacobsen in the chemical dictionary of [[Albert Ladenburg]] in the 1880s.<ref>[[#Hesse|Hesse]], pp. 1–3</ref><ref>Oscar Jacobsen, "Alkaloide" in:  Ladenburg, ''Handwörterbuch der Chemie'' (Breslau, Germany:  Eduard Trewendt, 1882), vol. 1, [http://books.google.com/books?id=-9fUAAAAMAAJ&pg=PA213 pp. 213–422].</ref>
----
''begin copy''


We call him Adrian Doyle here, Conan Doyle there, Doyle elsewhere, and instruct to sort by 'Conandoyle'. Libraries make Doyle the surname.[http://viaf.org/viaf/100257437/]  
There is no unique method of naming alkaloids.<ref name="Hesse 5">[[#Hesse|Hesse]], p. 5</ref> Many individual names are formed by adding the suffix "ine" to the species or genus name.<ref>The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa (belladonna)": [https://webspace.yale.edu/chem125/125/history99/5Valence/Nomenclature/alkanenames.html Development of Systematic Names for the Simple Alkanes]. yale.edu</ref> For example, [[atropine]] is isolated from the plant [[Atropa belladonna]], [[strychnine]] is obtained from the seed of [[Strychnine tree]]  (''Strychnos nux-vomica'' L.).<ref name="XimE: alkaloidy"/> If several alkaloids are extracted from one plant then their names often contain suffixes "idine", "anine", "aline", "inine", etc. There are also at least 86 alkaloids containing the root "vin" (extracted from the [[Vinca]] plant).<ref>[[#Hesse|Hesse]], p. 7</ref>


In the father's biography we provide some discussion [[Arthur Conan Doyle#Name]] with the weight of evidence or practice heavily on the 'Doyle' side, and we use 'Doyle' in running prose. But again we instruct to sort by 'Conandoyle'. Libraries make Doyle the surname.[http://viaf.org/viaf/65283845/]
== History ==
[[File:Friedrich Wilhelm Adam Sertuerner.jpg|thumb|left|[[Friedrich Sertürner]], the German chemist who first isolated [[morphine]] from [[opium]].]]
The Sir ACD Literary Estate official website[ uses 'Conan Doyle' on the homepage, where it does not use 'Doyle' alone.[http://www.sherlockholmesonline.org/TheEstate/] The NYT obituary  headline writer uses 'Conan Doyle' but the text uses 'Lady Doyle'.[http://www.nytimes.com/learning/general/onthisday/bday/0522.html]
Alkaloid-containing plants have been used by humans since ancient times for therapeutic and recreational purposes. For example, medicinal plants have been known in the [[Mesopotamia]] at least around 2000 BC.<ref name="Aniszewski 182">[[#Aniszewski|Aniszewski]], p. 182</ref> The ''[[Odyssey]]'' of [[Homer]] referred to a gift given to Helen by the Egyptian queen, a drug bringing oblivion. It is believed that the gift was an opium-containing drug.<ref>[[#Hesse|Hesse]], p. 338</ref> A Chinese book on houseplants written in 1st–3rd centuries BC mentioned a medical use of [[Ephedra]] and [[Opium poppy|opium poppies]].<ref>[[#Hesse|Hesse]], p. 304</ref> Also, [[coca]] leaves have been used by [[South America]]n Indians since ancient times.<ref>[[#Hesse|Hesse]], p. 350</ref>


--[[User:P64|P64]] ([[User talk:P64|talk]]) 21:49, 2 October 2013 (UTC)
[[Extracts]] from plants containing toxic alkaloids, such as [[aconitine]] and [[tubocurarine]], were used since antiquity for poisoning arrows.<ref name="Aniszewski 182"/>


''end copy''
Studies of alkaloids began in the 19th century. In 1804, the German chemist [[Friedrich Sertürner]] isolated from opium a "soporific principle" ({{lang-la|principium somniferum}}), which he called "morphium" in honor of [[Morpheus (mythology)|Morpheus]], the [[Ancient Greece|Greek]] god of dreams; in German and some other Central-European languages, this is still the name of the drug. The term "morphine", used in English and French, was given by the French physicist [[Joseph Louis Gay-Lussac]].
----
:"The Sir ACD Literary Estate" isn't connected to the Doyle family heirs and shouldn't be taken as any definitive statement (and even if there were an official website, it could use both depending on the copywriter; not everyone gets concerned about the same matters). Without wanting to detour the ACD copyrights have been a source of dispute for decades ultimately stemming from different children of ACD and various sales & reclaims, and that site is based on an ownership claim stemming from a 1970s sale outside the family (and disputes the subsequent termination of transfer). [[User:Timrollpickering|Timrollpickering]] ([[User talk:Timrollpickering|talk]]) 23:05, 2 October 2013 (UTC)


::Just to ensure we are consistent, if nothing else, I've put the surname only mentions to Doyle, rather than Conan Doyle. It's a moot point which should be the preferred style, but we do need to stick to one over the other. Given what we say in the [[Arthur Conan Doyle#Name|name section]], Doyle seems to be as good a place as any. - [[User:SchroCat|SchroCat]] ([[User talk:SchroCat|talk]]) 07:42, 14 October 2013 (UTC)
A significant contribution to the chemistry of alkaloids in the early years of its development was made by the French researchers [[Pierre Joseph Pelletier]] and [[Joseph Bienaimé Caventou]], who discovered [[quinine]] (1820) and [[strychnine]] (1818). Several other alkaloids were discovered around that time, including [[xanthine]] (1817), [[atropine]] (1819), [[caffeine]] (1820), [[coniine]] (1827), [[nicotine]] (1828), [[colchicine]] (1833), [[sparteine]] (1851), and [[cocaine]] (1860).<ref>[[#Hesse|Hesse]], pp. 313–316</ref>


::: I made the same change, among other things, at [[Adrian Conan Doyle]]. Thus Arthur and Adrian would be listed side-by-side in categories {{c|English mystery writers}} and {{c|English short story writers}} --but Sir Arthur is exclusively Scottish. Anyway they both show up under D in most categories --as daughter [[Jean Conan Doyle]] does not, as we explain in her lead.
The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist [[Albert Ladenburg]]. He produced [[coniine]] by reacting 2-methylpyridine with [[acetaldehyde]] and reducing the resulting 2-propenyl pyridine with [[sodium]].<ref name="BSE: koniin">[http://slovari.yandex.ru/dict/bse/article/00036/77600.htm Кониин]. [[Great Soviet Encyclopedia]] (1969–1978)</ref><ref>[[#Hesse|Hesse]], p. 204</ref> The development of the chemistry of alkaloids was accelerated by the emergence of [[spectroscopy|spectroscopic]] and [[Chromatography|chromatographic]] methods in the 20th century, so that by 2008 more than 12,000 alkaloids had been identified.<ref>[[#Begley|Begley]], Natural Products in Plants</ref>


----
[[File:Bufotenin.svg|thumb|160px|[[Bufotenin]], an alkaloid from some toads, contains an [[indole]] core and is produced in living organisms from the amino acid [[tryptophan]].]]


::: By the way, the US national library reports many "Sources" of surname usage for Arthur and his Lady.[http://id.loc.gov/authorities/names/n79082292.html]  
== Classification ==
::: --[[User:P64|P64]] ([[User talk:P64|talk]]) 20:08, 14 October 2013 (UTC)
[[File:Nicotine.svg|thumb|160px|The [[nicotine]] molecule contains both [[pyridine]] (left) and [[pyrrolidine]] rings (right).]]


==Edit request==
Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids.<ref name="ref15">[[#Hesse|Hesse]], p. 11</ref> First classification methods have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.<ref name="XimE: alkaloidy"/><ref>[[#Orekhov|Orekhov]], p. 6</ref>
{{Edit semi-protected|ans=yes}}
Arthur Conan Doyle is distantly related to Bram Stoker the author <ref>http://en.wikipedia.org/wiki/Bram_Stoker</ref>


[[Special:Contributions/80.44.233.127|80.44.233.127]] ([[User talk:80.44.233.127|talk]]) 17:29, 20 November 2013 (UTC)
More recent classifications are based on similarity of the carbon skeleton (e.g., [[indole]]-, [[isoquinoline]]-, and [[pyridine]]-like) or biogenetic precursor ([[ornithine]], [[lysine]], [[tyrosine]], [[tryptophan]], etc.).<ref name="XimE: alkaloidy"/> However, they require compromises in borderline cases;<ref name="ref15" /> for example, [[nicotine]] contains a pyridine fragment from [[nicotinamide]] and [[pyrrolidine]] part from ornithine<ref>[[#Aniszewski|Aniszewski]], p. 109</ref> and therefore can be assigned to both classes.<ref name="ref19">[[#Dewick|Dewick]], p. 307</ref>


[[File:Red information icon with gradient background.svg|20px|link=|alt=]] '''Not done:''' please make your request in a "change X to Y" format.<!-- Template:ESp --> Also, you need a [[WP:RS|reliable source]] for this. Wikipedia is not a reliable source, but you may be able to find the source of that claim in the references for that article. Thanks, [[User:Celestra|Celestra]] ([[User talk:Celestra|talk]]) 19:55, 20 November 2013 (UTC)
Alkaloids are often divided into the following major groups:<ref>[[#Hesse|Hesse]], p. 12</ref>
 
# "True alkaloids", which contain [[nitrogen]] in the [[heterocycle]] and originate from [[amino acid]]s.<ref name="ref21">[[#Plemenkov|Plemenkov]], p. 223</ref> Their characteristic examples are [[atropine]], [[nicotine]], and [[morphine]]. This group also includes some alkaloids that besides nitrogen heterocycle contain [[terpene]] (e.g., [[evonine]]<ref>[[#Aniszewski|Aniszewski]], p. 108</ref>) or peptide fragments (e.g. [[ergotamine]]<ref name="ref23">[[#Hesse|Hesse]], p. 84</ref>). This group also includes piperidine alkaloids [[coniine]] and [[coniceine]]<ref name="ref24">[[#Hesse|Hesse]], p. 31</ref> although they do not originate from amino acids.<ref name="ref25">[[#Dewick|Dewick]], p. 381</ref>
# "Protoalkaloids", which contain [[nitrogen]] and also originate from amino acids.<ref name="ref21" /> Examples include [[mescaline]], [[adrenaline]] and [[ephedrine]].
# Polyamine alkaloids – derivatives of [[putrescine]], [[spermidine]], and [[spermine]].
# Peptide and cyclopeptide alkaloids.<ref name="ref27">{{cite journal|author = Dimitris C. Gournelif, Gregory G. Laskarisb and Robert Verpoorte|title = Cyclopeptide alkaloids|doi = 10.1039/NP9971400075|journal = Nat. Prod. Rep.|year = 1997|volume = 14|pages = 75–82|pmid = 9121730|issue = 1}}</ref>
# Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids.<ref>[[#Aniszewski|Aniszewski]], p. 11</ref> This group includes, [[terpene]]-like and [[steroid]]-like alkaloids,<ref>[[#Plemenkov|Plemenkov]], p. 246</ref> as well as [[purine]]-like alkaloids such as [[caffeine]], [[theobromine]], [[theacrine]] and [[theophylline]].<ref name="ref30">[[#Aniszewski|Aniszewski]], p. 12</ref> Some authors classify as pseudoalkaloids such compounds such as [[ephedrine]] and [[cathinone]]. Those originate from the amino acid [[phenylalanine]], but acquire their nitrogen atom not from the amino acid but through [[transamination]].<ref name="ref30" /><ref name="ref31">[[#Dewick|Dewick]], p. 382</ref>
 
Some alkaloids do not have the carbon skeleton characteristic of their group. So, [[galantamine]] and homoaporphines do not contain [[isoquinoline]] fragment, but are, in general, attributed to isoquinoline alkaloids.<ref>[[#Hesse|Hesse]], pp. 44, 53</ref>
 
Main classes of monomeric alkaloids are listed in the table below:
<!--the table is translated from the ru.wiki article. Please fix translation glitches -->
{| Class = "wikitable"
|-
! Class
!Major groups
!Main synthesis steps
!Examples
|-
| colspan="4"  style="text-align:center; background:# DADADA;"|''Alkaloids with nitrogen heterocycles (true alkaloids)''
|-
| [[Pyrrolidine]] derivatives<ref name="ref34">[[#Plemenkov|Plemenkov]], p. 224</ref>
[[File:Pyrrolidine structure.svg|50px|center]]
|
| [[Ornithine]] or [[arginine]] → [[putrescine]] → N-methylputrescine → N-methyl-Δ<sup>1</sup>-pyrroline <ref name="ref35">[[#Aniszewski|Aniszewski]], p. 75</ref>
| [[Cuscohygrine]], [[hygrine]], hygroline, stachydrine<ref name="ref34" /><ref>[[#Orekhov|Orekhov]], p. 33</ref>
|-
| Rowspan = "2"|[[Tropane]] derivatives<ref name="ref38">[http://www.xumuk.ru/encyklopedia/2/4609.html Chemical Encyclopedia: Tropan alkaloids]. xumuk.ru</ref>
[[File:Tropane numbered.svg|100px|center]]
| Atropine group<br /><small>Substitution in positions 3, 6 or 7 </small>
| Rowspan = "2"|[[Ornithine]] or [[arginine]] → [[putrescine]] → N-methylputrescine → N-methyl-Δ<sup>1</sup>-pyrroline <ref name = "ref35 "/>
| [[Atropine]], [[scopolamine]], [[hyoscyamine]]<ref name="ref34" /><ref name="ref38" /><ref>[[#Hesse|Hesse]], p. 34</ref>
|-
| Cocaine group<br /> <small>Substitution in positions 2 and 3 </small>
| [[Cocaine]], [[ecgonine]] <ref name="ref38" /><ref>[[#Aniszewski|Aniszewski]], p. 27</ref>
|-
| Rowspan = "4"|[[Pyrrolizidine]] derivatives<ref name="ref45">[http://www.xumuk.ru/encyklopedia/2/3370.html Chemical Encyclopedia: Pyrrolizidine alkaloids]. xumuk.ru</ref>
[[File:Pyrrolizidine.svg|80px|center]]
| Non-esters
| Rowspan = "3"|In plants: [[ornithine]] or [[arginine]] → [[putrescine]] → [[homospermidine]] → [[retronecine]] <ref name="ref35" />
| [[Retronecine]], heliotridine, laburnine <ref name="ref45" /><ref>[[#Plemenkov|Plemenkov]], p. 229</ref>
|-
| Complex [[esters]] of monocarboxylic acids
| Indicine, lindelophin, sarracine <ref name="ref45" />
|-
| Macrocyclic diesters
| [[Platyphylline]], trichodesmine<ref name="ref45" />
|-
| 1-aminopyrrolizidines ([[Loline alkaloids|lolines]])
| In [[Neotyphodium|fungi]]: [[Proline|<small>L</small>-proline]] + [[homoserine|<small>L</small>-homoserine]] → ''N''-(3-amino-3-carboxypropyl)proline → norloline<ref name="Blankenship">{{cite journal|author=Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL|year= 2005|title=Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids|journal=Chembiochem|volume=6|pages=1016–1022|pmid=15861432|doi=10.1002/cbic.200400327|issue=6}}</ref><ref name="Faulkner et al. 2006">{{cite journal|author=Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL|year= 2006|title=On the sequence of bond formation in loline alkaloid biosynthesis|journal=Chembiochem|volume=7|pages=1078–1088|pmid=16755627|doi=10.1002/cbic.200600066|issue=7}}</ref>
|Loline, ''N''-formylloline, ''N''-acetylloline<ref name="Schardl et al. 2007">{{cite journal|author=Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP|year=2007|title=Loline alkaloids: currencies of mutualism|journal = [[Phytochemistry (journal)|Phytochemistry]]|volume=68|pages=980–996|doi=10.1016/j.phytochem.2007.01.010|pmid=17346759|issue=7}}</ref>
|-
| Rowspan = "2"|[[Piperidine]] derivatives<ref>[[#Plemenkov|Plemenkov]], p. 225</ref>
[[File:Piperidin.svg|50px|center]]
|
| [[Lysine]] → [[cadaverine]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 95</ref>
| [[Sedamine]], lobeline, anaferine, [[piperine]] <ref name="ref24" /><ref>[[#Orekhov|Orekhov]], p. 80</ref>
|-
|
| [[Caprylic acid|Octanoic acid]] → coniceine → [[coniine]] <ref name="ref25" />
| [[Coniine]], coniceine <ref name="ref25" />
|-
| Rowspan = "5"|[[Quinolizidine]] derivatives<ref name="ref57">[http://www.xumuk.ru/encyklopedia/2/5011.html Chemical Encyclopedia: Quinolizidine alkaloids]. xumuk.ru</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 93</ref>
[[File:Quinolizidine.svg|80px|center]]
| [[Lupinine]] group
| Rowspan = "5"|[[Lysine]] → [[cadaverine]] → Δ<sup>1</sup>-piperideine <ref>[[#Aniszewski|Aniszewski]], p. 98</ref>
| [[Lupinine]], nupharidin <ref name="ref57" />
|-
| [[Cytisine]] group
| [[Cytisine]] <ref name="ref57" />
|-
| [[Sparteine]] group
| [[Sparteine]], [[lupanine]], [[anahygrine]]<ref name="ref57" />
|-
| [[Matrine]] group
| Matrine, oxymatrine, allomatridine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 91</ref><ref>{{cite journal|author = Joseph P. Michael|title = Indolizidine and quinolizidine alkaloids|doi = 10.1039/b208137g|journal=Nat. Prod. Rep|year = 2002|volume = 19|pages = 458–475}}</ref>
|-
| [[Ormosanine]] group
| Ormosanine, piptantine<ref name="ref57" /><ref>[[#Saxton|Saxton]], Vol. 1, p. 92</ref>
|-
| [[Indolizidine]] derivatives<ref>[[#Dewick|Dewick]], p. 310</ref>
[[File:Indolizidine.svg|80px|center]]
|
| [[Lysine]] → δ-semialdehyde of [[alpha-Aminoadipic acid|α-aminoadipic acid]] → [[pipecolic acid]] → 1 indolizidinone <ref>[[#Aniszewski|Aniszewski]], p. 96</ref>
| [[Swainsonine]], [[castanospermine]] <ref>[[#Aniszewski|Aniszewski]], p. 97</ref>
|-
| Rowspan = "4"|[[Pyridine]] derivatives<ref name="ref72">[[#Plemenkov|Plemenkov]], p. 227</ref><ref name="ref73">[http://www.xumuk.ru/encyklopedia/2/3336.html Chemical Encyclopedia: pyridine alkaloids]. xumuk.ru</ref>
[[File:Pyridine.svg|50px|center]]
| Simple derivatives of pyridine
| Rowspan = "3"|[[Nicotinic acid]] → dihydronicotinic acid → 1,2-dihydropyridine <ref name="ref74">[[#Aniszewski|Aniszewski]], p. 107</ref>
| [[Trigonelline]], ricinine, [[arecoline]] <ref name="ref72" /><ref name="ref76">[[#Aniszewski|Aniszewski]], p. 85</ref>
|-
| Polycyclic noncondensing pyridine derivatives
| [[Nicotine]], [[nornicotine]], [[anabasine]], anatabine <ref name="ref72" /><ref name="ref76" />
|-
| Polycyclic condensed pyridine derivatives
| [[Actinidine]], gentianine, pediculinine <ref>[[#Plemenkov|Plemenkov]], p. 228</ref>
|-
| [[Sesquiterpene]] pyridine derivatives
| [[Nicotinic acid]], [[isoleucine]] <ref name="Aniszewski 110"/>
| Evonine, hippocrateine, triptonine <ref name="ref73" /><ref name="ref74" />
|-
| Rowspan = "26"|[[Isoquinoline]] derivatives and related alkaloids <ref name="Hesse 36">[[#Hesse|Hesse]], p. 36</ref>
[[File:Isoquinoline numbered.svg|90px|center]]
| Simple derivatives of isoquinoline <ref name="XimE: izoxinolin">[http://www.xumuk.ru/encyklopedia/1642.html Chemical Encyclopedia: isoquinoline alkaloids]. xumuk.ru</ref>
| Rowspan = "26"|[[Tyrosine]] or [[phenylalanine]] → [[dopamine]] or [[tyramine]] (for alkaloids Amarillis) <ref>[[#Aniszewski|Aniszewski]], pp. 77–78</ref><ref name="Begley">[[#Begley|Begley]], Alkaloid Biosynthesis</ref>
| Salsoline, lophocerine <ref name="Hesse 36"/><ref name="XimE: izoxinolin"/>
|-
| Derivatives of 1- and 3-isoquinolines <ref name="Saxton 122">[[#Saxton|Saxton]], Vol. 3, p. 122</ref>
| N-methylcoridaldine, noroxyhydrastinine <ref name="Saxton 122"/>
|-
| Derivatives of 1- and 4-phenyltetrahydroisoquinolines <ref name="XimE: izoxinolin"/>
| Cryptostilin <ref name="XimE: izoxinolin"/><ref name="Hesse 54">[[#Hesse|Hesse]], p. 54</ref>
|-
| Derivatives of 5-naftil-isoquinoline <ref name="ref83">[[#Hesse|Hesse]], p. 37</ref>
| Ancistrocladine <ref name="ref83" />
|-
| Derivatives of 1- and 2-benzyl-izoquinolines <ref>[[#Hesse|Hesse]], p. 38</ref>
| [[Papaverine]], [[laudanosine]], sendaverine
|-
| [[Cularine]] group<ref name="ref86">[[#Hesse|Hesse]], p. 46</ref>
| Cularine, yagonine <ref name="ref86" />
|-
| [[Pavine (molecule)|Pavine]]s and isopavines <ref name="ref88">[[#Hesse|Hesse]], p. 50</ref>
| Argemonine, [[amurensine]] <ref name="ref88" />
|-
| Benzopyrrocolines <ref name="ref90">{{cite journal|author = Kenneth W. Bentley|title = β-Phenylethylamines and the isoquinoline alkaloids|doi = 10.1039/NP9971400387|journal=Nat. Prod. Rep|year = 1997|volume = 14|pages = 387–411|pmid = 9281839|issue = 4|url=http://chemistry.mdma.ch/hiveboard/rhodium/pdf/archive/merbst/phenethylamines%20and%20isoquinolines%202001.pdf}}</ref>
| Cryptaustoline <ref name="XimE: izoxinolin"/>
|-
| Protoberberines <ref name="XimE: izoxinolin"/>
| [[Berberine]], [[canadine]], ophiocarpine, mecambridine, corydaline <ref name="ref91">[[#Hesse|Hesse]], p. 47</ref>
|-
| Phthalidisoquinolines <ref name="XimE: izoxinolin"/>
| [[Hydrastine]], [[narcotine]] (Noscapine) <ref>[[#Hesse|Hesse]], p. 39</ref>
|-
| Spirobenzylisoquinolines <ref name="XimE: izoxinolin"/>
| Fumaricine <ref name="ref88" />
|-
| [[Psychotria ipecacuanha|Ipecacuanha]] alkaloids<ref name="ref94">[[#Hesse|Hesse]], p. 41</ref>
| Emetine, protoemetine, ipecoside <ref name="ref94" />
|-
| Benzophenanthridines <ref name="XimE: izoxinolin"/>
| Sanguinarine, oxynitidine, corynoloxine <ref name="ref96">[[#Hesse|Hesse]], p. 49</ref>
|-
| [[Aporphine]]s <ref name="XimE: izoxinolin"/>
| [[Glaucine]], coridine, liriodenine <ref>[[#Hesse|Hesse]], p. 44</ref>
|-
| Proaporphines <ref name="XimE: izoxinolin"/>
| Pronuciferine, glaziovine <ref name="XimE: izoxinolin"/><ref name="ref90" />
|-
| Homoaporphines <ref name="ref99">[[#Saxton|Saxton]], Vol. 3, p. 164</ref>
| Kreysiginine, multifloramine <ref name="ref99" />
|-
| Homoproaporphines <ref name="ref99" />
| Bulbocodine <ref name="ref86" />
|-
| [[Morphine]]s<ref name="ref103">[[#Hesse|Hesse]], p. 51</ref>
| [[Morphine]], [[codeine]], [[thebaine]], [[sinomenine]] <ref name="ref104">[[#Plemenkov|Plemenkov]], p. 236</ref>
|-
| Homomorphines <ref>[[#Saxton|Saxton]], Vol. 3, p. 163</ref>
| Kreysiginine, androcymbine <ref name="ref103" />
|-
| Tropoloisoquinolines <ref name="XimE: izoxinolin"/>
| Imerubrine <ref name="XimE: izoxinolin"/>
|-
| Azofluoranthenes <ref name="XimE: izoxinolin"/>
| Rufescine, imeluteine <ref>[[#Saxton|Saxton]], Vol. 3, p. 168</ref>
|-
| [[Amaryllis]] alkaloids<ref>[[#Hesse|Hesse]], p. 52</ref>
| [[Lycorine]], ambelline, tazettine, [[galantamine]], montanine <ref>[[#Hesse|Hesse]], p. 53</ref>
|-
| [[Erythrina]] alkaloids<ref name="Hesse 54"/>
| Erysodine, erythroidine <ref name="Hesse 54"/>
|-
| [[Phenanthrene]] derivatives <ref name="XimE: izoxinolin"/>
| Atherosperminine <ref name="XimE: izoxinolin"/><ref name="ref91" />
|-
| [[Protopin]]s <ref name="XimE: izoxinolin"/>
| Protopine, oxomuramine, corycavidine <ref name="ref96" />
|-
| Aristolactam <ref name="XimE: izoxinolin"/>
| Doriflavin <ref name="XimE: izoxinolin"/>
|-
| [[Oxazole]] derivatives<ref name="Plemenkov 241">[[#Plemenkov|Plemenkov]], p. 241</ref>
[[File:Oxazole structure.svg|80px|center]]
|
| [[Tyrosine]] → [[tyramine]] <ref>[[#Brossi|Brossi]], Vol. 35, p. 261</ref>
| Annuloline, halfordinol, texaline, texamine<ref>[[#Brossi|Brossi]], Vol. 35, pp. 260–263</ref>
|-
| [[Isoxazole]] derivatives
[[Image:isoxazole structure.png|80px|center]]
|
|[[Ibotenic acid]] → [[Muscimol]]
|Ibotenic acid, Muscimol
|-
| [[Thiazole]] derivatives<ref name="ref114">[[#Plemenkov|Plemenkov]], p. 242</ref>
[[File:Thiazole structure.svg|80px|center]]
|
| [[1-Deoxy-D-xylulose 5-phosphate]] (DOXP), [[tyrosine]], [[cysteine]] <ref>[[#Begley|Begley]], Cofactor Biosynthesis</ref>
| Nostocyclamide, thiostreptone <ref name="ref114" /><ref>{{cite journal|author = John R. Lewis|title = Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids|journal = Nat. Prod. Rep|year = 2000|volume = 17|pages = 57–84|pmid = 10714899|issue = 1|doi = 10.1039/a809403i}}</ref>
|-
| Rowspan = "3"|[[Quinazoline]] derivatives<ref>[http://www.xumuk.ru/encyklopedia/2/5003.html Chemical Encyclopedia: Quinazoline alkaloids]. xumuk.ru</ref>
[[File:Quinazoline numbered.svg|90px|center]]
| 3,4-Dihydro-4-quinazolone derivatives
| Rowspan = "3"|[[Anthranilic acid]] or [[phenylalanine]] or [[ornithine]] <ref>[[#Aniszewski|Aniszewski]], p. 106</ref>
| [[Febrifugine]]<ref name="ref120">[[#Aniszewski|Aniszewski]], p. 105</ref>
|-
| 1,4-Dihydro-4-quinazolone derivatives
| Glycorine, arborine, glycosminine<ref name="ref120" />
|-
| Pyrrolidine and piperidine quinazoline derivatives
| [[Vazicine]] (peganine) <ref name="Plemenkov 241"/>
|-
| [[Acridine]] derivatives<ref name="Plemenkov 241"/>
[[File:Acridine.svg|100px|center]]
|
| [[Anthranilic acid]] <ref>{{cite journal|author = Richard B. Herbert|title = The biosynthesis of plant alkaloids and nitrogenous microbial metabolites|journal=Nat. Prod. Rep|year = 1999|volume = 16|pages = 199–208|doi = 10.1039/a705734b|last2 = Herbert|first2 = Richard B.|last3 = Herbert|first3 = Richard B.}}</ref>
| Rutacridone, [[acronicine]]<ref>[[#Plemenkov|Plemenkov]], pp. 231, 246</ref><ref>[[#Hesse|Hesse]], p. 58</ref>
|-
| Rowspan = "4"|[[Quinoline]] derivatives<ref>[[#Plemenkov|Plemenkov]], p. 231</ref><ref name="ref126">[http://www.xumuk.ru/encyklopedia/2/5014.html Chemical Encyclopedia: Quinoline alkaloids]. xumuk.ru</ref>
[[File:Quinoline numbered.svg|90px|center]]
| Simple derivatives of quinoline derivatives of 2 – [[quinolones]] and 4-quinolone
| Rowspan = "3"|[[Anthranilic acid]] → 3-carboxyquinoline <ref name="ref127">[[#Aniszewski|Aniszewski]], p. 114</ref>
| Cusparine, [[echinopsine]], evocarpine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 205</ref><ref>[[#Hesse|Hesse]], p. 55</ref>
|-
| Tricyclic terpenoids
| Flindersine<ref name="ref126" /><ref name="ref131">[[#Plemenkov|Plemenkov]], p. 232</ref>
|-
| Furanoquinoline derivatives
| [[Dictamnine]], fagarine, skimmianine<ref name="ref126" /><ref>[[#Orekhov|Orekhov]], p. 212</ref><ref>[[#Aniszewski|Aniszewski]], p. 118</ref>
|-
| [[Quinine]]s
| [[Tryptophan]] → [[tryptamine]] → [[strictosidine]] (with [[secologanin]]) → korinanteal → [[cinhoninon]] <ref name="Begley"/><ref name = " ref127 "/>
| [[Quinine]], [[quinidine]], [[cinchonine]], cinhonidine <ref name="ref131" />
|-
| Rowspan = "10"|[[Indole]] derivatives<ref name="ref104" />
[[File:Indole numbered.svg|100px|center]]
{{See also|indole alkaloids}}
| colspan="3" style="text-align:center;"|''Non-isoprene indole alkaloids''
|-
| Simple indole derivatives <ref name="ref140">[[#Aniszewski|Aniszewski]], p. 112</ref>
| Rowspan = "3"|[[Tryptophan]] → [[tryptamine]] or 5-hydroxitriptofan <ref name="ref141">[[#Aniszewski|Aniszewski]], p. 113</ref>
| [[Serotonin]], [[psilocybin]], [[dimethyltryptamine]] (DMT), [[bufotenin]] <ref>[[#Hesse|Hesse]], p. 15</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 467</ref>
|-
| Simple derivatives of [[beta-carboline|β-carboline]] <ref>[[#Dewick|Dewick]], pp. 349–350</ref>
| Harman, [[harmine]], [[harmaline]], eleagnine <ref name="ref140" />
|-
| Pyrroloindole alkaloids <ref name="ref152">[[#Aniszewski|Aniszewski]], p. 119</ref>
| [[Physostigmine]] (eserine), etheramine, physovenine, eptastigmine<ref name="ref152" />
|-
| colspan="3" style="text-align:center;"|''Semiterpenoid indole alkaloids''
|-
| [[Ergoline|Ergot alkaloids]]<ref name="ref104" />
| [[Tryptophan]] → chanoclavine → agroclavine → elimoclavine → [[paspalic acid]] → [[lysergic acid]] <ref name="ref152" />
| [[Ergotamine]], ergobasine, ergosine<ref>[[#Hesse|Hesse]], p. 29</ref>
|-
| colspan="3" style="text-align:center;"|''Monoterpenoid indole alkaloids''
|-
| ''Corynanthe'' type alkaloids<ref name="ref141" />
| Rowspan = "3"|[[Tryptophan]] → [[tryptamine]] → [[strictosidine]] (with [[secologanin]]) <ref name="ref141" />
| Ajmalicine, sarpagine, vobasine, [[ajmaline]], [[yohimbine]], [[reserpine]], [[mitragynine]],<ref>[[#Hesse|Hesse]], pp. 23–26</ref><ref>[[#Saxton|Saxton]], Vol. 1, p. 169</ref> group [[strychnine]] and ([[Strychnine]] [[brucine]], aquamicine, [[vomicine]] <ref>[[#Saxton|Saxton]], Vol. 5, p. 210</ref>)
|-
| [[Iboga]]-type alkaloids<ref name="ref141" />
| [[Ibogamine]], [[ibogaine]], [[voacangine]]<ref name="ref141" />
|-
| [[Aspidosperma]]-type alkaloids<ref name="ref141" />
| [[Vincamine]], [[vinca alkaloids]], vincotine, aspidospermine<ref>[[#Hesse|Hesse]], pp. 17–18</ref><ref>[[#Dewick|Dewick]], p. 357</ref>
|-
| [[Imidazole]] derivatives<ref name="Plemenkov 241"/>
[[File:Imidazole structure.svg|50px|center]]
|
| Directly from [[histidine]]<ref name="Aniszewski 104">[[#Aniszewski|Aniszewski]], p. 104</ref>
| [[Histamine]], pilocarpine, pilosine, stevensine<ref name="Plemenkov 241"/><ref name="Aniszewski 104"/>
|-
| [[Purine]] derivatives<ref>[[#Hesse|Hesse]], p. 72</ref>
[[File:Purin2.svg|90px|center]]
|
| [[Xanthosine]] (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl [[xanthine]] → [[theobromine]] → [[caffeine]] <ref name="Begley"/>
| [[Caffeine]], [[theobromine]], [[theophylline]], [[saxitoxin]] <ref>[[#Hesse|Hesse]], p. 73</ref><ref>[[#Dewick|Dewick]], p. 396</ref>
|-
| colspan="4"  style="text-align:center; background:# DADADA;"|''Alkaloids with nitrogen in the side chain (protoalkaloids)''
|-
| β-[[Phenylethylamine]] derivatives<ref name="ref90" />
[[File:Phenylethylamine numbered.svg|110px|center]]
|
| [[Tyrosine]] or [[phenylalanine]] → [[dioxyphenilalanine]] → [[dopamine]] → [[adrenaline]] and [[mescaline]] [[tyrosine]] → [[tyramine]] phenylalanine → 1-phenylpropane-1,2-dione → [[cathinone]] → [[ephedrine]] and [[pseudoephedrine]] <ref name="Aniszewski 110"/><ref name="ref31" /><ref>[http://www.plantcyc.org:1555/PLANT/NEW-IMAGE?type=NIL&object=PWY-5883 PlantCyc Pathway: ephedrine biosynthesis]{{dead link|date=March 2013}}</ref>
| [[Tyramine]], [[ephedrine]], [[pseudoephedrine]], [[mescaline]], [[cathinone]], [[catecholamines]] ([[adrenaline]], [[noradrenaline]], [[dopamine]])<ref name="Aniszewski 110"/><ref>[[#Hesse|Hesse]], p. 76</ref>
|-
| [[Colchicine]] alkaloids <ref name="ref179">[http://www.xumuk.ru/encyklopedia/2069.html Chemical Encyclopedia: colchicine alkaloids]. xumuk.ru</ref>
[[File:Colchicine.svg|120px|center]]
|
| [[Tyrosine]] or [[phenylalanine]] → [[dopamine]] → [[autumnaline]] → [[colchicine]] <ref>[[#Aniszewski|Aniszewski]], p. 77</ref>
| [[Colchicine]], colchamine<ref name="ref179" />
|-
| [[Muscarine]] <ref name="ref182">[[#Hesse|Hesse]], p. 81</ref>
[[File:Muscarine.svg|100px|center]]
|
| [[Glutamic acid]] → 3-ketoglutamic acid → muscarine (with [[pyruvic acid]])<ref>[[#Brossi|Brossi]], Vol. 23, p. 376</ref>
| [[Muscarine]], allomuscarine, epimuscarine, epiallomuscarine<ref name="ref182" />
|-
| Benzylamine<ref name="ref185">[[#Hesse|Hesse]], p. 77</ref>
[[File:Benzylamine.svg|90px|center]]
|
| [[Phenylalanine]] with [[valine]], [[leucine]] or [[isoleucine]]<ref>[[#Brossi|Brossi]], Vol. 23, p. 268</ref>
| [[Capsaicin]], [[dihydrocapsaicin]], nordihydrocapsaicin <ref name="ref185" /><ref>[[#Brossi|Brossi]], Vol. 23, p. 231</ref>
|-
| colspan="4"  style="text-align:center; background:# DADADA;"|''Polyamines alkaloids''
|-
| [[Putrescine]] derivatives<ref name="ref189">[[#Hesse|Hesse]], p. 82</ref>
[[File:Putrescine.svg|90px|center]]
|
| Rowspan = "3"|[[ornithine]] → [[putrescine]] → [[spermidine]] → [[spermine]]<ref>[http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/misc/spermine.html Spermine Biosynthesis]</ref>
| Paucine <ref name="ref189" />
|-
| [[Spermidine]] derivatives<ref name="ref189" />
[[File:Spermidine.svg|110px|center]]
|
| Lunarine, codonocarpine<ref name="ref189" />
|-
| [[Spermine]] derivatives<ref name="ref189" />
[[File:Spermine.svg|130px|center]]
|
| Verbascenine, aphelandrine <ref name="ref189" />
|-
| colspan="4"  style="text-align:center; background:# DADADA;"|''Peptide (cyclopeptide) alkaloids''
|-
| Rowspan = "2"|Peptide alkaloids with a 13-membered cycle <ref name="ref27" /><ref name="ref196">[[#Plemenkov|Plemenkov]], p. 243</ref>
| Nummularine C type
| Rowspan = "8"|From different amino acids <ref name="ref27" />
| Nummularine C, Nummularine S <ref name="ref27" />
|-
| [[Ziziphine]] type
| Ziziphine A, sativanine H <ref name="ref27" />
|-
| Rowspan = "5"|Peptide alkaloids with a 14-membered cycle <ref name="ref27" /><ref name="ref196" />
| Frangulanine type
| Frangulanine, scutianine J <ref name="ref196" />
|-
| Scutianine A type
| Scutianine A <ref name="ref27" />
|-
| Integerrine type
| Integerrine, discarine D <ref name="ref196" />
|-
| Amphibine F type
| Amphibine F, spinanine A <ref name="ref27" />
|-
| Amfibine B type
| Amphibine B, lotusine C <ref name="ref27" />
|-
| Peptide alkaloids with a 15-membered cycle <ref name="ref196" />
| Mucronine A type
| Mucronine A <ref name="ref23" /><ref name="ref196" />
|-
| colspan="4"  style="text-align:center; background:# DADADA;"|''Pseudoalkaloids ([[terpenes]] and [[steroids]])''
|-
| Diterpenes <ref name="ref23" />
[[File:Isoprene.svg|80px|center]]
| Lycoctonine type
| [[Mevalonic acid]] → [[izopentenilpyrophosfate]] → [[geranyl pyrophosphate]] <ref>[http://www.xumuk.ru/encyklopedia/2/4392.html Chemical Encyclopedia: Terpenes]. xumuk.ru</ref><ref>[[#Begley|Begley]], Natural Products: An Overview</ref>
| [[Aconitine]], [[delphinine]] <ref name="ref23" /><ref>{{cite journal|author = Atta-ur-Rahman and M. Iqbal Choudhary|title = Diterpenoid and steroidal alkaloids|url = http://www.rsc.org/publishing/journals/NP/article.asp?doi=NP9971400191|journal=Nat. Prod. Rep|year = 1997|volume = 14|pages = 191–203|pmid = 9149410|issue = 2|doi = 10.1039/np9971400191}}</ref>
|-
| [[Steroids]]<ref>[[#Hesse|Hesse]], p. 88</ref>
[[File:Cyclopentenophenanthrene.svg|100px|center]]
|
| [[Cholesterol]], [[arginine]]<ref>[[#Dewick|Dewick]], p. 388</ref>
| Solasodine, [[solanidine]], veralkamine, [[batrachotoxin]]<ref>[[#Plemenkov|Plemenkov]], p. 247</ref>
|}
 
== Properties ==
[[File:Cyclopelamb2.jpg|thumb|Head of a lamb born by a sheep that ate leaves of the [[Veratrum californicum|corn lily]] plant. The [[cyclopia]] in the calf is induced by the alkaloid [[cyclopamine]] present in the plant.]]
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as [[nicotine]]<ref>[http://slovari.yandex.ru/dict/bse/article/00052/84600.htm Никотин]. [[Great Soviet Encyclopedia]] (1969–1978)</ref> or [[coniine]],<ref name="BSE: koniin"/> are typically volatile, colorless, oily liquids.<ref name="ref222">[[#Grinkevich|Grinkevich]], p. 131</ref> Some alkaloids are colored, like [[berberine]] (yellow) and [[sanguinarine]] (orange).<ref name="ref222" />
 
Most alkaloids are weak bases, but some, such as [[theobromine]] and [[theophylline]], are [[amphoteric]].<ref name="ref225">G. A. Spiller [http://books.google.com/books?id=Rgs_rVOceZwC&pg=PA140 ''Caffeine''], CRC Press, 1997 ISBN 0-8493-2647-8</ref> Many alkaloids dissolve poorly in water but readily dissolve in [[organic solvent]]s, such as [[diethyl ether]], [[chloroform]] or [[1,2-dichloroethane]]. [[Caffeine]],<ref>{{cite web|title=Caffeine|url=http://www.drugbank.ca/drugs/DB00201|work=DrugBank|accessdate=12 February 2013}}</ref> [[cocaine]],<ref>{{cite web|title=Cocaine|url=http://www.drugbank.ca/drugs/DB00907|work=DrugBank|accessdate=12 February 2013}}</ref> [[codeine]]<ref>{{cite web|title=Codeine|url=http://www.drugbank.ca/drugs/DB00318|work=DrugBank|accessdate=12 February 2013}}</ref> and [[nicotine]]<ref>{{cite web|title=Nicotine|url=http://www.drugbank.ca/drugs/DB00184|work=DrugBank|accessdate=12 February 2013}}</ref> are water soluble (with a solubility of ≥1g/L), whereas others, including [[morphine]]<ref>{{cite web|title=Morphine|url=http://www.drugbank.ca/drugs/DB00295|work=DrugBank|accessdate=12 February 2013}}</ref> and [[yohimbine]]<ref>{{cite web|title=Yohimbine|url=http://www.drugbank.ca/drugs/DB01392|work=DrugBank|accessdate=12 February 2013}}{{dead link|date=March 2013}}</ref> are highly water soluble (0.1–1 g/L). Alkaloids and acids form salts of various strengths. These salts are usually soluble in water and [[alcohol]] and poorly soluble in most organic solvents. Exceptions include [[scopolamine]] hydrobromide, which is soluble in organic solvents, and the water-soluble quinine sulfate.<ref name="ref222" />
 
Most alkaloids have a bitter taste or are poisonous when ingested. Alkaloid production in plants appeared to have evolved in response to feeding by herbivorous animals; however, some animals have evolved the ability to detoxify alkaloids.<ref>[[#Fattorusso|Fattorusso]], p. 53</ref>  Some alkaloids can produce developmental defects in the offspring of animals that consume but cannot detoxify the alkaloids.  One example is the alkaloid [[cyclopamine]], produced in the leaves of [[Veratrum californicum|corn lily]]. During the 1950s, up to 25% of lambs born by sheep that had grazed on corn lily had serious facial deformations. These ranged from deformed jaws to [[cyclopia]] (see picture). After decades of research, in the 1980s, the compound responsible for these deformities was identified as the alkaloid 11-deoxyjervine, later renamed to cyclopamine.<ref>{{cite book|page=362|url=http://books.google.com/?id=nixyqfGIGHcC&pg=PA362|title=Poisonous plants and related toxins, Volume 2001|author=Thomas Acamovic, Colin S. Stewart, T. W. Pennycott|publisher=CABI|year= 2004|isbn=0-85199-614-0}}</ref>
 
==Distribution in nature==
[[File:Strychnos nux-vomica - Köhler–s Medizinal-Pflanzen-266.jpg|thumb|[[Strychnine tree]]. Its seeds are rich in [[strychnine]] and [[brucine]].]]
 
Alkaloids are [[anabolism|generated]] by various living organisms, especially by [[Vascular plant|higher plants]] – about 10 to 25% of those contain alkaloids.<ref>[[#Aniszewski|Aniszewski]], p. 13</ref><ref>[[#Orekhov|Orekhov]], p. 11</ref> Therefore, in the past the term "alkaloid" was associated with plants.<ref name="Hesse 4">[[#Hesse|Hesse]], p.4</ref>
 
The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant tissues. Depending on the type of plants, the maximum concentration is observed in the leaves ([[black henbane]]), [[fruit]]s or [[seed]]s ([[Strychnine tree]]), root ([[Rauwolfia serpentina]]) or bark ([[cinchona]]).<ref>[[#Grinkevich|Grinkevich]], pp. 122–123</ref> Furthermore, different tissues of the same plants may contain different alkaloids.<ref>[[#Orekhov|Orekhov]], p. 12</ref>
 
Beside plants, alkaloids are found in certain types of [[fungi]], such as [[psilocybin]] in the fungus of the genus [[Psilocybe]], and in animals, such as [[bufotenin]] in the skin of some toads.<ref name="Hesse 5" /> Many marine organisms also contain alkaloids.<ref>[[#Fattorusso|Fattorusso]], p. XVII</ref> Some [[amines]], such as [[adrenaline]] and [[serotonin]], which play an important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids.<ref>[[#Aniszewski|Aniszewski]], pp. 110–111</ref>
 
==Extraction==
[[File:Piperine crystals.jpg|thumb|Crystals of [[piperine]] extracted from [[black pepper]].]]
 
Because of the structural diversity of alkaloids, there is no single method of their extraction from natural raw materials.<ref name="Hesse 116">[[#Hesse|Hesse]], p. 116</ref> Most methods exploit the property of most alkaloids to be soluble in organic solvents but not in water, and the opposite tendency of their salts.
 
Most plants contain several alkaloids. Their mixture is extracted first and then individual alkaloids are separated.<ref name="ref236">[[#Grinkevich|Grinkevich]], p. 132</ref> Plants are thoroughly ground before extraction.<ref name="Hesse 116"/><ref>[[#Grinkevich|Grinkevich]], p. 5</ref> Most alkaloids are present in the raw plants in the form of salts of organic acids.<ref name="Hesse 116"/> The extracted alkaloids may remain salts or change into bases.<ref name="ref236" /> Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, the impurities are dissolved by weak acids; this converts alkaloid bases into salts that are washed away with water. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organic solvent. The process is repeated until the desired purity is achieved.
 
In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., [[acetic acid]] in water, ethanol, or methanol). A base is then added to convert alkaloids to basic forms that are extracted with organic solvent (if the extraction was performed with alcohol, it is removed first, and the remainder is dissolved in water). The solution is purified as described above.<ref name="Hesse 116"/><ref>[[#Grinkevich|Grinkevich]], pp. 132–134</ref>
 
Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by [[distillation]].<ref>[[#Grinkevich|Grinkevich]], pp. 134–136</ref>
 
==Biosynthesis==
Biological precursors of most alkaloids are [[amino acid]]s, such as [[ornithine]], [[lysine]], [[phenylalanine]], [[tyrosine]], [[tryptophan]], [[histidine]], [[aspartic acid]], and [[anthranilic acid]].<ref name="Plemenkov 253">[[#Plemenkov|Plemenkov]], p. 253</ref> [[Nicotinic acid]] can be synthesized from tryptophan or aspartic acid. Ways of alkaloid biosynthesis are too numerous and cannot be easily classified.<ref name="Begley"/> However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of [[Schiff bases]] and [[Mannich reaction]].<ref name="Plemenkov 253"/>
 
===Synthesis of Schiff bases===
{{Main|Schiff base}}
 
Schiff bases can be obtained by reacting amines with ketones or aldehydes.<ref>[[#Plemenkov|Plemenkov]], p. 254</ref> These reactions are a common method of producing C=N bonds.<ref name="Dewick 19">[[#Dewick|Dewick]], p. 19</ref>
 
[[File:Schiff base formation.svg|center]]
 
In the biosynthesis of alkaloids, such reactions may take place within a molecule,<ref name="Plemenkov 253"/> such as in the synthesis of piperidine:<ref name="ref19"/>
 
[[File:Schiff base formation intramolecular.svg|center]]
 
===Mannich reaction===
{{Main|Mannich reaction}}
 
An integral component of the Mannich reaction, in addition to an amine and a [[carbonyl]] compound, is a [[carbanion]], which plays the role of the nucleophile in the [[nucleophilic addition]] to the ion formed by the reaction of the amine and the carbonyl.<ref name = "Dewick 19" />
 
[[File:Mannich.png|center]]
 
The Mannich reaction can proceed both intermolecularly and intramolecularly:<ref>[[#Plemenkov|Plemenkov]], p. 255</ref><ref>[[#Dewick|Dewick]], p. 305</ref>
 
[[File:Mannich reaction intramolecular.svg|center]]
 
==Dimer alkaloids==
In addition to the described above monomeric alkaloids, there are also [[Dimer (chemistry)|dimer]]ic, and even [[trimer (chemistry)|trimer]]ic and [[tetramer]]ic alkaloids formed upon condensation of two, three, and four monomeric alkaloids. Dimeric alkaloids are usually formed from monomers of the same type through the following mechanisms:<ref>[[#Hesse|Hesse]], pp. 91–105</ref>
* [[Mannich reaction]], resulting in, e.g., voacamine
* [[Michael reaction]] (villalstonine)
* Condensation of aldehydes with amines (toxiferine)
* Oxidative addition of phenols (dauricine, tubocurarine)
* [[Lactone|Lactonization]] (carpaine).
 
<center>
<gallery widths="220px" perrow="3">
File:Voacamine chemical structure.png|[[Voacamine]]
File:Villalstonine.svg|[[Villalstonine]]
File:Toxiferine I.png|[[Toxiferine]]
File:Dauricine.svg|[[Dauricine]]
File:Tubocurarine.svg|[[Tubocurarine]]
File:Carpaine.png|[[Carpaine]]
</gallery>
</center>
 
==The biological role==
The role of alkaloids for living organisms that produce them is still unclear.<ref>[[#Aniszewski|Aniszewski]], p. 142</ref> It was initially assumed that the alkaloids are the final products of [[nitrogen]] [[metabolism]] in plants, as [[urea]] in mammals. It was later shown that alkaloid concentrations varies over time, and this hypothesis was refuted.<ref name="Meyers"/>
 
Most of the known functions of alkaloids are related to protection. For example, [[aporphine]] alkaloid [[liriodenine]] produced by the [[Liriodendron tulipifera|tulip tree]] protects it from parasitic mushrooms. In addition, presence of alkaloids in the plant prevents insects and [[chordate]] animals from eating it. However, some animals adapted to alkaloids and even use them in their own metabolism.<ref>[[#Hesse|Hesse]], pp. 283–291</ref> Such alkaloid-related substances as [[serotonin]], [[dopamine]] and [[histamine]] are important [[neurotransmitter]]s in animals. Alkaloids are also known to regulate plant growth.<ref>[[#Aniszewski|Aniszewski]], pp. 142–143</ref> Another example of an organism that uses alkaloids for protection is the ''[[Utetheisa ornatrix]]'', more commonly known as the Ornate Moth. Pyrrolizidine alkaloids render these larvae and adult moths unpalatable to many of their natural enemies like coccinelid beetles, green lacewings, insectivorous hemiptera and insectivorous bats.<ref>W.E. Conner (2009). ''Tiger Moths and Woolly Bears—behaviour, ecology, and evolution of the Arctiidae''. New York: Oxford University Press. pp. 1–10. ISBN 0195327373.</ref>
 
== Applications ==
 
===In medicine===
Medical use of alkaloid-containing plants has a long history, and, thus, when the first alkaloids were isolated in the 19th century, they immediately found application in clinical practice.<ref>[[#Hesse|Hesse]], p. 303</ref> Many alkaloids are still used in medicine, usually in the form of salts, including the following:<ref name="Meyers"/><ref>[[#Hesse|Hesse]], pp. 303–309</ref>
 
{| Class = "wikitable"
|-
! Alkaloid
! Action
|-
| [[Ajmaline]]
| [[Antiarrhythmic agent|antiarrhythmic]]
|-
| [[Atropine]], [[scopolamine]], [[hyoscyamine]]
| [[anticholinergic]]
|-
| [[Caffeine]]
| [[Stimulant]], [[Adenosine receptor]] antagonist
|-
| [[Codeine]]
| [[cough medicine]], [[analgesic]]
|-
| [[Colchicine]]
| remedy for [[gout]]
|-
| [[Emetine]]
| [[antiprotozoal agent]]
|-
| [[Ergoline|Ergot alkaloids]]
| [[Sympathomimetics|sympathomimetic]], vasodilator, antihypertensive
|-
| [[Morphine]]
| [[analgesic]]
|-
| [[Nicotine]]
| [[Stimulant]], [[Nicotinic agonist|Nicotinic acetylcholine receptor agonist]]
|-
| [[Physostigmine]]
| inhibitor of [[acetylcholinesterase]]
|-
| [[Quinidine]]
| antiarrhythmic
|-
| [[Quinine]]
| antipyretics, antimalarial
|-
| [[Reserpine]]
| [[Antihypertensive drug|antihypertensive]]
|-
| [[Tubocurarine]]
| Muscle relaxant
|-
| [[Vinblastine]], [[vincristine]]
| [[Chemotherapy|antitumor]]
|-
| [[Vincamine]]
| [[Vasodilation|vasodilating]], [[Antihypertensive drug|antihypertensive]]
|-
| [[Yohimbine]]
| [[Stimulant]], [[Aphrodisiac]]
|}
 
Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were designed to enhance or change the primary effect of the drug and reduce unwanted side-effects.<ref>[[#Hesse|Hesse]], p. 309</ref> For example, [[naloxone]], an [[opioid receptor]] [[receptor antagonist|antagonist]], is a derivative of [[thebaine]] that is present in [[opium]].<ref>[[#Dewick|Dewick]], p. 335</ref>
 
<center>
<gallery widths="200px" perrow="2">
File:Thebaine skeletal.svg|[[Thebaine]]
File:Naloxone.svg|[[Naloxone]]
</gallery>
</center>
 
=== In agriculture ===
Prior to the development of a wide range of relatively low-toxic synthetic [[pesticide]]s, some alkaloids, such as salts of nicotine and [[anabasine]], were used as [[insecticide]]s. Their use was limited by their high toxicity to humans.<ref>György Matolcsy, Miklós Nádasy, Viktor Andriska [http://books.google.com/books?id=fPiRSsUOpLEC&pg=PA21 ''Pesticide chemistry''], Elsevier, 2002, pp. 21–22 ISBN 0-444-98903-X</ref>
 
=== Use as psychoactive drugs ===
Preparations of plants containing alkaloids and their extracts, and later pure alkaloids, have long been used as [[Psychoactive drug|psychoactive substances]]. [[Cocaine]] and [[cathinone]] are [[stimulant]]s of the [[central nervous system]].<ref>[[#Veselovskaya|Veselovskaya]], p. 75</ref><ref>[[#Hesse|Hesse]], p. 79</ref> [[Mescaline]] and many of indole alkaloids (such as [[psilocybin]], [[dimethyltryptamine]] and [[ibogaine]]) have [[hallucinogen]]ic effect.<ref>[[#Veselovskaya|Veselovskaya]], p. 136</ref><ref>Geoffrey A. Cordell ''The Alkaloids: Chemistry and Biology''. [http://www.sciencedirect.com/science/bookseries/10994831/56 Vol. 56], Elsevier, 2001, p. 8, ISBN 978-0-12-469556-6.</ref> [[Morphine]] and [[codeine]] are strong narcotic pain killers.<ref>[[#Veselovskaya|Veselovskaya]], p. 6</ref>
 
There are alkaloids that do not have strong psychoactive effect themselves, but are [[precursor (chemistry)|precursor]]s for semi-synthetic psychoactive drugs. For example, [[ephedrine]] and [[pseudoephedrine]] are used to produce [[methcathinone]] and [[methamphetamine]].<ref>[[#Veselovskaya|Veselovskaya]], pp. 51–52</ref> [[Thebaine]] is used in the synthesis of many painkillers such as [[oxycodone]].
 
== See also ==
{{colbegin|3}}
* [[Amine]]
* [[Base (chemistry)]]
* [[Natural products]]
* [[Palau'amine]]
* [[Secondary metabolite]]
* [[Mayer's reagent]]
{{colend}}
 
== Notes ==
{{Reflist|group="nb"}}
 
== References ==
{{Reflist|25em}}
 
== Bibliography ==
{{Commons|Alkaloid}}
* {{cite book|ref=Aniszewski|author = Aniszewski, Tadeusz |title = Alkaloids – secrets of life|location = Amsterdam|publisher = [[Elsevier]]|year = 2007|isbn = 978-0-444-52736-3}}
* {{cite book|ref=Begley|author = Begley, Tadhg P. |title = Encyclopedia of Chemical Biology|year = 2009|publisher = Wiley|isbn = 978-0-471-75477-0|doi=10.1002/cbic.200900262}}
* {{cite book|ref=Brossi|author =Brossi, Arnold |title=The Alkaloids: Chemistry and Pharmacology|publisher= Academic Press|year= 1989}}
* {{cite book|ref=Dewick|author = Dewick, Paul M |title = Medicinal Natural Products. A Biosynthetic Approach. Second Edition|year = 2002|publisher = Wiley|isbn = 0-471-49640-5}}
* {{cite book|ref=Fattorusso|author = Fattorusso, E. and Taglialatela-Scafati, O. |title = Modern Alkaloids: Structure, Isolation, Synthesis and Biology|year = 2008|publisher = Wiley-VCH|isbn = 978-3-527-31521-5}}
* {{cite book|ref=Grinkevich|author = Grinkevich NI Safronich LN|title = The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities|location = M|year = 1983}}
* {{cite book|ref=Hesse|author = Hesse, Manfred |title = Alkaloids: Nature's Curse or Blessing?|year = 2002|publisher = Wiley-VCH|isbn = 978-3-906390-24-6}}
* {{cite book|ref=Knunyants|author = Knunyants, IL|title = Chemical Encyclopedia|url = http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm|publisher = Soviet Encyclopedia|year = 1988}}
* {{cite book|ref=Orekhov|author = Orekhov, AP|title = Chemistry alkaloids|edition = Acad. 2|location = M.|publisher = USSR|year = 1955}}
* {{cite book|ref=Plemenkov|author = Plemenkov, VV|title = Introduction to the Chemistry of Natural Compounds|location = Kazan|year = 2001}}
*{{cite book|ref=Saxton|author =Saxton, J. E. |title=The Alkaloids. A Specialist Periodical Report|place= London|publisher= The Chemical Society|year=1971}}
* {{cite book|ref=Veselovskaya|author =Veselovskaya, N. B., Kovalenko, A.E |title=Drugs|place=Moscow|publisher= Triada-X|year=2000}}
 
{{alkaloids}}
 
[[Category:Alkaloids|*]]
 
{{Link GA|ru}}

Revision as of 18:23, 19 August 2014

29 yr old Orthopaedic Surgeon Grippo from Saint-Paul, spends time with interests including model railways, top property developers in singapore developers in singapore and dolls. Finished a cruise ship experience that included passing by Runic Stones and Church.

File:Papaver somniferum 01.jpg
The first individual alkaloid, morphine, was isolated in 1804 from poppy (Papaver somniferum).[1]

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral[2] and even weakly acidic properties.[3] Some synthetic compounds of similar structure are also attributed to alkaloids.[4] In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.[5]

Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals, and are part of the group of natural products (also called secondary metabolites). Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine, the psychedelic psilocin, the stimulant caffeine, nicotine,[6] the analgesic morphine, the antibacterial berberine, the anticancer compound vincristine, the antihypertension agent reserpine, the cholinomimeric galantamine, the spasmolysis agent atropine, the vasodilator vincamine, the anti-arrhythmia compound quinidine, the anti-asthma therapeutic ephedrine, and the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.[7]

The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.[8] Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids.[2] Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids.[9] Some authors, however, consider alkaloids a special case of amines.[10][11][12]

Naming

File:Meissner alkalod definition article 1819.png
The article that introduced the concept of "alkaloid".

The name "alkaloids" (Template:Lang-de) was introduced in 1819 by the German chemist Carl Friedrich Wilhelm Meißner, and is derived from late Latin root Template:Lang-la (which, in turn, comes from the Arabic al-qalwī – "ashes of plants") and the suffix Fitter (Basic ) Bud from Rosemere, has lots of pursuits that include robotics, property developers service Apartments in singapore singapore and aerobics. Has just concluded a trip to City of Cuzco. – "like".[nb 1] However, the term came into wide use only after the publication of a review article by Oscar Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s.[13][14]

There is no unique method of naming alkaloids.[15] Many individual names are formed by adding the suffix "ine" to the species or genus name.[16] For example, atropine is isolated from the plant Atropa belladonna, strychnine is obtained from the seed of Strychnine tree (Strychnos nux-vomica L.).[5] If several alkaloids are extracted from one plant then their names often contain suffixes "idine", "anine", "aline", "inine", etc. There are also at least 86 alkaloids containing the root "vin" (extracted from the Vinca plant).[17]

History

File:Friedrich Wilhelm Adam Sertuerner.jpg
Friedrich Sertürner, the German chemist who first isolated morphine from opium.

Alkaloid-containing plants have been used by humans since ancient times for therapeutic and recreational purposes. For example, medicinal plants have been known in the Mesopotamia at least around 2000 BC.[18] The Odyssey of Homer referred to a gift given to Helen by the Egyptian queen, a drug bringing oblivion. It is believed that the gift was an opium-containing drug.[19] A Chinese book on houseplants written in 1st–3rd centuries BC mentioned a medical use of Ephedra and opium poppies.[20] Also, coca leaves have been used by South American Indians since ancient times.[21]

Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since antiquity for poisoning arrows.[18]

Studies of alkaloids began in the 19th century. In 1804, the German chemist Friedrich Sertürner isolated from opium a "soporific principle" (Template:Lang-la), which he called "morphium" in honor of Morpheus, the Greek god of dreams; in German and some other Central-European languages, this is still the name of the drug. The term "morphine", used in English and French, was given by the French physicist Joseph Louis Gay-Lussac.

A significant contribution to the chemistry of alkaloids in the early years of its development was made by the French researchers Pierre Joseph Pelletier and Joseph Bienaimé Caventou, who discovered quinine (1820) and strychnine (1818). Several other alkaloids were discovered around that time, including xanthine (1817), atropine (1819), caffeine (1820), coniine (1827), nicotine (1828), colchicine (1833), sparteine (1851), and cocaine (1860).[22]

The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist Albert Ladenburg. He produced coniine by reacting 2-methylpyridine with acetaldehyde and reducing the resulting 2-propenyl pyridine with sodium.[23][24] The development of the chemistry of alkaloids was accelerated by the emergence of spectroscopic and chromatographic methods in the 20th century, so that by 2008 more than 12,000 alkaloids had been identified.[25]

File:Bufotenin.svg
Bufotenin, an alkaloid from some toads, contains an indole core and is produced in living organisms from the amino acid tryptophan.

Classification

File:Nicotine.svg
The nicotine molecule contains both pyridine (left) and pyrrolidine rings (right).

Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids.[26] First classification methods have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.[5][27]

More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-, and pyridine-like) or biogenetic precursor (ornithine, lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in borderline cases;[26] for example, nicotine contains a pyridine fragment from nicotinamide and pyrrolidine part from ornithine[28] and therefore can be assigned to both classes.[29]

Alkaloids are often divided into the following major groups:[30]

  1. "True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids.[31] Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine[32]) or peptide fragments (e.g. ergotamine[33]). This group also includes piperidine alkaloids coniine and coniceine[34] although they do not originate from amino acids.[35]
  2. "Protoalkaloids", which contain nitrogen and also originate from amino acids.[31] Examples include mescaline, adrenaline and ephedrine.
  3. Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine.
  4. Peptide and cyclopeptide alkaloids.[36]
  5. Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids.[37] This group includes, terpene-like and steroid-like alkaloids,[38] as well as purine-like alkaloids such as caffeine, theobromine, theacrine and theophylline.[39] Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.[39][40]

Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline alkaloids.[41]

Main classes of monomeric alkaloids are listed in the table below:

Class Major groups Main synthesis steps Examples
Alkaloids with nitrogen heterocycles (true alkaloids)
Pyrrolidine derivatives[42]
File:Pyrrolidine structure.svg
 Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ1-pyrroline [43] Cuscohygrine, hygrine, hygroline, stachydrine[42][44]
Tropane derivatives[45]
File:Tropane numbered.svg
 Atropine group
Substitution in positions 3, 6 or 7 		Ornithine or arginine → putrescine → N-methylputrescine → N-methyl-Δ1-pyrroline [43] Atropine, scopolamine, hyoscyamine[42][45][46]
Cocaine group
Substitution in positions 2 and 3 		Cocaine, ecgonine [45][47]
Pyrrolizidine derivatives[48]
File:Pyrrolizidine.svg
 Non-esters In plants: ornithine or arginine → putrescine → homospermidine → retronecine [43] Retronecine, heliotridine, laburnine [48][49]
Complex esters of monocarboxylic acids Indicine, lindelophin, sarracine [48]
Macrocyclic diesters Platyphylline, trichodesmine[48]
1-aminopyrrolizidines (lolines) In fungi: L-proline + L-homoserine → N-(3-amino-3-carboxypropyl)proline → norloline[50][51] Loline, N-formylloline, N-acetylloline[52]
Piperidine derivatives[53]
File:Piperidin.svg
 Lysine → cadaverine → Δ1-piperideine [54] Sedamine, lobeline, anaferine, piperine [34][55]
Octanoic acid → coniceine → coniine [35] Coniine, coniceine [35]
Quinolizidine derivatives[56][57]
File:Quinolizidine.svg
 Lupinine group Lysine → cadaverine → Δ1-piperideine [58] Lupinine, nupharidin [56]
Cytisine group Cytisine [56]
Sparteine group Sparteine, lupanine, anahygrine[56]
Matrine group Matrine, oxymatrine, allomatridine[56][59][60]
Ormosanine group Ormosanine, piptantine[56][61]
Indolizidine derivatives[62]
File:Indolizidine.svg
 Lysine → δ-semialdehyde of α-aminoadipic acid → pipecolic acid → 1 indolizidinone [63] Swainsonine, castanospermine [64]
Pyridine derivatives[65][66]
File:Pyridine.svg
 Simple derivatives of pyridine Nicotinic acid → dihydronicotinic acid → 1,2-dihydropyridine [67] Trigonelline, ricinine, arecoline [65][68]
Polycyclic noncondensing pyridine derivatives Nicotine, nornicotine, anabasine, anatabine [65][68]
Polycyclic condensed pyridine derivatives Actinidine, gentianine, pediculinine [69]
Sesquiterpene pyridine derivatives Nicotinic acid, isoleucine [12] Evonine, hippocrateine, triptonine [66][67]
Isoquinoline derivatives and related alkaloids [70]
File:Isoquinoline numbered.svg
 Simple derivatives of isoquinoline [71] Tyrosine or phenylalanine → dopamine or tyramine (for alkaloids Amarillis) [72][73] Salsoline, lophocerine [70][71]
Derivatives of 1- and 3-isoquinolines [74] N-methylcoridaldine, noroxyhydrastinine [74]
Derivatives of 1- and 4-phenyltetrahydroisoquinolines [71] Cryptostilin [71][75]
Derivatives of 5-naftil-isoquinoline [76] Ancistrocladine [76]
Derivatives of 1- and 2-benzyl-izoquinolines [77] Papaverine, laudanosine, sendaverine
Cularine group[78] Cularine, yagonine [78]
Pavines and isopavines [79] Argemonine, amurensine [79]
Benzopyrrocolines [80] Cryptaustoline [71]
Protoberberines [71] Berberine, canadine, ophiocarpine, mecambridine, corydaline [81]
Phthalidisoquinolines [71] Hydrastine, narcotine (Noscapine) [82]
Spirobenzylisoquinolines [71] Fumaricine [79]
Ipecacuanha alkaloids[83] Emetine, protoemetine, ipecoside [83]
Benzophenanthridines [71] Sanguinarine, oxynitidine, corynoloxine [84]
Aporphines [71] Glaucine, coridine, liriodenine [85]
Proaporphines [71] Pronuciferine, glaziovine [71][80]
Homoaporphines [86] Kreysiginine, multifloramine [86]
Homoproaporphines [86] Bulbocodine [78]
Morphines[87] Morphine, codeine, thebaine, sinomenine [88]
Homomorphines [89] Kreysiginine, androcymbine [87]
Tropoloisoquinolines [71] Imerubrine [71]
Azofluoranthenes [71] Rufescine, imeluteine [90]
Amaryllis alkaloids[91] Lycorine, ambelline, tazettine, galantamine, montanine [92]
Erythrina alkaloids[75] Erysodine, erythroidine [75]
Phenanthrene derivatives [71] Atherosperminine [71][81]
Protopins [71] Protopine, oxomuramine, corycavidine [84]
Aristolactam [71] Doriflavin [71]
Oxazole derivatives[93]
File:Oxazole structure.svg
 Tyrosine → tyramine [94] Annuloline, halfordinol, texaline, texamine[95]
Isoxazole derivatives
File:Isoxazole structure.png
 Ibotenic acid → Muscimol Ibotenic acid, Muscimol
Thiazole derivatives[96]
File:Thiazole structure.svg
 1-Deoxy-D-xylulose 5-phosphate (DOXP), tyrosine, cysteine [97] Nostocyclamide, thiostreptone [96][98]
Quinazoline derivatives[99]
File:Quinazoline numbered.svg
 3,4-Dihydro-4-quinazolone derivatives Anthranilic acid or phenylalanine or ornithine [100] Febrifugine[101]
1,4-Dihydro-4-quinazolone derivatives Glycorine, arborine, glycosminine[101]
Pyrrolidine and piperidine quinazoline derivatives Vazicine (peganine) [93]
Acridine derivatives[93]
File:Acridine.svg
 Anthranilic acid [102] Rutacridone, acronicine[103][104]
Quinoline derivatives[105][106]
File:Quinoline numbered.svg
 Simple derivatives of quinoline derivatives of 2 – quinolones and 4-quinolone Anthranilic acid → 3-carboxyquinoline [107] Cusparine, echinopsine, evocarpine[106][108][109]
Tricyclic terpenoids Flindersine[106][110]
Furanoquinoline derivatives Dictamnine, fagarine, skimmianine[106][111][112]
Quinines Tryptophan → tryptamine → strictosidine (with secologanin) → korinanteal → cinhoninon [73][107] Quinine, quinidine, cinchonine, cinhonidine [110]
Indole derivatives[88]
File:Indole numbered.svg

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Non-isoprene indole alkaloids
Simple indole derivatives [113] Tryptophan → tryptamine or 5-hydroxitriptofan [114] Serotonin, psilocybin, dimethyltryptamine (DMT), bufotenin [115][116]
Simple derivatives of β-carboline [117] Harman, harmine, harmaline, eleagnine [113]
Pyrroloindole alkaloids [118] Physostigmine (eserine), etheramine, physovenine, eptastigmine[118]
Semiterpenoid indole alkaloids
Ergot alkaloids[88] Tryptophan → chanoclavine → agroclavine → elimoclavine → paspalic acid → lysergic acid [118] Ergotamine, ergobasine, ergosine[119]
Monoterpenoid indole alkaloids
Corynanthe type alkaloids[114] Tryptophan → tryptamine → strictosidine (with secologanin) [114] Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, mitragynine,[120][121] group strychnine and (Strychnine brucine, aquamicine, vomicine [122])
Iboga-type alkaloids[114] Ibogamine, ibogaine, voacangine[114]
Aspidosperma-type alkaloids[114] Vincamine, vinca alkaloids, vincotine, aspidospermine[123][124]
Imidazole derivatives[93]
File:Imidazole structure.svg
 Directly from histidine[125] Histamine, pilocarpine, pilosine, stevensine[93][125]
Purine derivatives[126]
File:Purin2.svg
 Xanthosine (formed in purine biosynthesis) → 7 methylxantosine → 7-methyl xanthine → theobromine → caffeine [73] Caffeine, theobromine, theophylline, saxitoxin [127][128]
Alkaloids with nitrogen in the side chain (protoalkaloids)
β-Phenylethylamine derivatives[80]
File:Phenylethylamine numbered.svg
 Tyrosine or phenylalanine → dioxyphenilalanine → dopamine → adrenaline and mescaline tyrosine → tyramine phenylalanine → 1-phenylpropane-1,2-dione → cathinone → ephedrine and pseudoephedrine [12][40][129] Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, dopamine)[12][130]
Colchicine alkaloids [131]
File:Colchicine.svg
 Tyrosine or phenylalanine → dopamine → autumnaline → colchicine [132] Colchicine, colchamine[131]
Muscarine [133]
File:Muscarine.svg
 Glutamic acid → 3-ketoglutamic acid → muscarine (with pyruvic acid)[134] Muscarine, allomuscarine, epimuscarine, epiallomuscarine[133]
Benzylamine[135]
File:Benzylamine.svg
 Phenylalanine with valine, leucine or isoleucine[136] Capsaicin, dihydrocapsaicin, nordihydrocapsaicin [135][137]
Polyamines alkaloids
Putrescine derivatives[138]
File:Putrescine.svg
 ornithine → putrescine → spermidine → spermine[139] Paucine [138]
Spermidine derivatives[138]
File:Spermidine.svg
 Lunarine, codonocarpine[138]
Spermine derivatives[138]
File:Spermine.svg
 Verbascenine, aphelandrine [138]
Peptide (cyclopeptide) alkaloids
Peptide alkaloids with a 13-membered cycle [36][140] Nummularine C type From different amino acids [36] Nummularine C, Nummularine S [36]
Ziziphine type Ziziphine A, sativanine H [36]
Peptide alkaloids with a 14-membered cycle [36][140] Frangulanine type Frangulanine, scutianine J [140]
Scutianine A type Scutianine A [36]
Integerrine type Integerrine, discarine D [140]
Amphibine F type Amphibine F, spinanine A [36]
Amfibine B type Amphibine B, lotusine C [36]
Peptide alkaloids with a 15-membered cycle [140] Mucronine A type Mucronine A [33][140]
Pseudoalkaloids (terpenes and steroids)
Diterpenes [33]
File:Isoprene.svg
 Lycoctonine type Mevalonic acid → izopentenilpyrophosfate → geranyl pyrophosphate [141][142] Aconitine, delphinine [33][143]
Steroids[144]
File:Cyclopentenophenanthrene.svg
 Cholesterol, arginine[145] Solasodine, solanidine, veralkamine, batrachotoxin[146]

Properties

File:Cyclopelamb2.jpg
Head of a lamb born by a sheep that ate leaves of the corn lily plant. The cyclopia in the calf is induced by the alkaloid cyclopamine present in the plant.

Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine[147] or coniine,[23] are typically volatile, colorless, oily liquids.[148] Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).[148]

Most alkaloids are weak bases, but some, such as theobromine and theophylline, are amphoteric.[149] Many alkaloids dissolve poorly in water but readily dissolve in organic solvents, such as diethyl ether, chloroform or 1,2-dichloroethane. Caffeine,[150] cocaine,[151] codeine[152] and nicotine[153] are water soluble (with a solubility of ≥1g/L), whereas others, including morphine[154] and yohimbine[155] are highly water soluble (0.1–1 g/L). Alkaloids and acids form salts of various strengths. These salts are usually soluble in water and alcohol and poorly soluble in most organic solvents. Exceptions include scopolamine hydrobromide, which is soluble in organic solvents, and the water-soluble quinine sulfate.[148]

Most alkaloids have a bitter taste or are poisonous when ingested. Alkaloid production in plants appeared to have evolved in response to feeding by herbivorous animals; however, some animals have evolved the ability to detoxify alkaloids.[156] Some alkaloids can produce developmental defects in the offspring of animals that consume but cannot detoxify the alkaloids. One example is the alkaloid cyclopamine, produced in the leaves of corn lily. During the 1950s, up to 25% of lambs born by sheep that had grazed on corn lily had serious facial deformations. These ranged from deformed jaws to cyclopia (see picture). After decades of research, in the 1980s, the compound responsible for these deformities was identified as the alkaloid 11-deoxyjervine, later renamed to cyclopamine.[157]

Distribution in nature

File:Strychnos nux-vomica - Köhler–s Medizinal-Pflanzen-266.jpg
Strychnine tree. Its seeds are rich in strychnine and brucine.

Alkaloids are generated by various living organisms, especially by higher plants – about 10 to 25% of those contain alkaloids.[158][159] Therefore, in the past the term "alkaloid" was associated with plants.[160]

The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant tissues. Depending on the type of plants, the maximum concentration is observed in the leaves (black henbane), fruits or seeds (Strychnine tree), root (Rauwolfia serpentina) or bark (cinchona).[161] Furthermore, different tissues of the same plants may contain different alkaloids.[162]

Beside plants, alkaloids are found in certain types of fungi, such as psilocybin in the fungus of the genus Psilocybe, and in animals, such as bufotenin in the skin of some toads.[15] Many marine organisms also contain alkaloids.[163] Some amines, such as adrenaline and serotonin, which play an important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids.[164]

Extraction

File:Piperine crystals.jpg
Crystals of piperine extracted from black pepper.

Because of the structural diversity of alkaloids, there is no single method of their extraction from natural raw materials.[165] Most methods exploit the property of most alkaloids to be soluble in organic solvents but not in water, and the opposite tendency of their salts.

Most plants contain several alkaloids. Their mixture is extracted first and then individual alkaloids are separated.[166] Plants are thoroughly ground before extraction.[165][167] Most alkaloids are present in the raw plants in the form of salts of organic acids.[165] The extracted alkaloids may remain salts or change into bases.[166] Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, the impurities are dissolved by weak acids; this converts alkaloid bases into salts that are washed away with water. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organic solvent. The process is repeated until the desired purity is achieved.

In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., acetic acid in water, ethanol, or methanol). A base is then added to convert alkaloids to basic forms that are extracted with organic solvent (if the extraction was performed with alcohol, it is removed first, and the remainder is dissolved in water). The solution is purified as described above.[165][168]

Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by distillation.[169]

Biosynthesis

Biological precursors of most alkaloids are amino acids, such as ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine, aspartic acid, and anthranilic acid.[170] Nicotinic acid can be synthesized from tryptophan or aspartic acid. Ways of alkaloid biosynthesis are too numerous and cannot be easily classified.[73] However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of Schiff bases and Mannich reaction.[170]

Synthesis of Schiff bases

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Schiff bases can be obtained by reacting amines with ketones or aldehydes.[171] These reactions are a common method of producing C=N bonds.[172]

File:Schiff base formation.svg

In the biosynthesis of alkaloids, such reactions may take place within a molecule,[170] such as in the synthesis of piperidine:[29]

File:Schiff base formation intramolecular.svg

Mannich reaction

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An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is a carbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the reaction of the amine and the carbonyl.[172]

File:Mannich.png

The Mannich reaction can proceed both intermolecularly and intramolecularly:[173][174]

File:Mannich reaction intramolecular.svg

Dimer alkaloids

In addition to the described above monomeric alkaloids, there are also dimeric, and even trimeric and tetrameric alkaloids formed upon condensation of two, three, and four monomeric alkaloids. Dimeric alkaloids are usually formed from monomers of the same type through the following mechanisms:[175]

The biological role

The role of alkaloids for living organisms that produce them is still unclear.[176] It was initially assumed that the alkaloids are the final products of nitrogen metabolism in plants, as urea in mammals. It was later shown that alkaloid concentrations varies over time, and this hypothesis was refuted.[8]

Most of the known functions of alkaloids are related to protection. For example, aporphine alkaloid liriodenine produced by the tulip tree protects it from parasitic mushrooms. In addition, presence of alkaloids in the plant prevents insects and chordate animals from eating it. However, some animals adapted to alkaloids and even use them in their own metabolism.[177] Such alkaloid-related substances as serotonin, dopamine and histamine are important neurotransmitters in animals. Alkaloids are also known to regulate plant growth.[178] Another example of an organism that uses alkaloids for protection is the Utetheisa ornatrix, more commonly known as the Ornate Moth. Pyrrolizidine alkaloids render these larvae and adult moths unpalatable to many of their natural enemies like coccinelid beetles, green lacewings, insectivorous hemiptera and insectivorous bats.[179]

Applications

In medicine

Medical use of alkaloid-containing plants has a long history, and, thus, when the first alkaloids were isolated in the 19th century, they immediately found application in clinical practice.[180] Many alkaloids are still used in medicine, usually in the form of salts, including the following:[8][181]

Alkaloid Action
Ajmaline antiarrhythmic
Atropine, scopolamine, hyoscyamine anticholinergic
Caffeine Stimulant, Adenosine receptor antagonist
Codeine cough medicine, analgesic
Colchicine remedy for gout
Emetine antiprotozoal agent
Ergot alkaloids sympathomimetic, vasodilator, antihypertensive
Morphine analgesic
Nicotine Stimulant, Nicotinic acetylcholine receptor agonist
Physostigmine inhibitor of acetylcholinesterase
Quinidine antiarrhythmic
Quinine antipyretics, antimalarial
Reserpine antihypertensive
Tubocurarine Muscle relaxant
Vinblastine, vincristine antitumor
Vincamine vasodilating, antihypertensive
Yohimbine Stimulant, Aphrodisiac

Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were designed to enhance or change the primary effect of the drug and reduce unwanted side-effects.[182] For example, naloxone, an opioid receptor antagonist, is a derivative of thebaine that is present in opium.[183]

In agriculture

Prior to the development of a wide range of relatively low-toxic synthetic pesticides, some alkaloids, such as salts of nicotine and anabasine, were used as insecticides. Their use was limited by their high toxicity to humans.[184]

Use as psychoactive drugs

Preparations of plants containing alkaloids and their extracts, and later pure alkaloids, have long been used as psychoactive substances. Cocaine and cathinone are stimulants of the central nervous system.[185][186] Mescaline and many of indole alkaloids (such as psilocybin, dimethyltryptamine and ibogaine) have hallucinogenic effect.[187][188] Morphine and codeine are strong narcotic pain killers.[189]

There are alkaloids that do not have strong psychoactive effect themselves, but are precursors for semi-synthetic psychoactive drugs. For example, ephedrine and pseudoephedrine are used to produce methcathinone and methamphetamine.[190] Thebaine is used in the synthesis of many painkillers such as oxycodone.

See also

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Notes

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References

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Bibliography

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  • 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

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  • 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

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Template:Alkaloids

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  1. ↑ 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

    My blog: http://www.primaboinca.com/view_profile.php?userid=5889534
  2. ↑ 2.0 2.1 IUPAC. Compendium of Chemical Terminology, 2nd ed. (The "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997) ISBN 0-9678550-9-8 21 year-old Glazier James Grippo from Edam, enjoys hang gliding, industrial property developers in singapore developers in singapore and camping. Finds the entire world an motivating place we have spent 4 months at Alejandro de Humboldt National Park.
  3. ↑ R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. – New York: Academic Press, 1965, p. 673
  4. ↑ Robert Alan Lewis. Lewis' dictionary of toxicology. CRC Press, 1998, p. 51 ISBN 1-56670-223-2
  5. ↑ 5.0 5.1 5.2 5.3 Chemical Encyclopedia: alkaloids. xumuk.ru
  6. ↑ Template:Cite web
  7. ↑ 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

    My blog: http://www.primaboinca.com/view_profile.php?userid=5889534
  8. ↑ 8.0 8.1 8.2 Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN 0-12-227411-3
  9. ↑ Leland J. Cseke Natural Products from Plants Second Edition. – CRC, 2006, p. 30 ISBN 0-8493-2976-0
  10. ↑ A. William Johnson Invitation to Organic Chemistry, Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6
  11. ↑ Raj K Bansal A Text Book of Organic Chemistry. 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1
  12. ↑ 12.0 12.1 12.2 12.3 Aniszewski, p. 110
  13. ↑ Hesse, pp. 1–3
  14. ↑ Oscar Jacobsen, "Alkaloide" in: Ladenburg, Handwörterbuch der Chemie (Breslau, Germany: Eduard Trewendt, 1882), vol. 1, pp. 213–422.
  15. ↑ 15.0 15.1 Hesse, p. 5
  16. ↑ The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa (belladonna)": Development of Systematic Names for the Simple Alkanes. yale.edu
  17. ↑ Hesse, p. 7
  18. ↑ 18.0 18.1 Aniszewski, p. 182
  19. ↑ Hesse, p. 338
  20. ↑ Hesse, p. 304
  21. ↑ Hesse, p. 350
  22. ↑ Hesse, pp. 313–316
  23. ↑ 23.0 23.1 Кониин. Great Soviet Encyclopedia (1969–1978)
  24. ↑ Hesse, p. 204
  25. ↑ Begley, Natural Products in Plants
  26. ↑ 26.0 26.1 Hesse, p. 11
  27. ↑ Orekhov, p. 6
  28. ↑ Aniszewski, p. 109
  29. ↑ 29.0 29.1 Dewick, p. 307
  30. ↑ Hesse, p. 12
  31. ↑ 31.0 31.1 Plemenkov, p. 223
  32. ↑ Aniszewski, p. 108
  33. ↑ 33.0 33.1 33.2 33.3 Hesse, p. 84
  34. ↑ 34.0 34.1 Hesse, p. 31
  35. ↑ 35.0 35.1 35.2 Dewick, p. 381
  36. ↑ 36.0 36.1 36.2 36.3 36.4 36.5 36.6 36.7 36.8 One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  37. ↑ Aniszewski, p. 11
  38. ↑ Plemenkov, p. 246
  39. ↑ 39.0 39.1 Aniszewski, p. 12
  40. ↑ 40.0 40.1 Dewick, p. 382
  41. ↑ Hesse, pp. 44, 53
  42. ↑ 42.0 42.1 42.2 Plemenkov, p. 224
  43. ↑ 43.0 43.1 43.2 Aniszewski, p. 75
  44. ↑ Orekhov, p. 33
  45. ↑ 45.0 45.1 45.2 Chemical Encyclopedia: Tropan alkaloids. xumuk.ru
  46. ↑ Hesse, p. 34
  47. ↑ Aniszewski, p. 27
  48. ↑ 48.0 48.1 48.2 48.3 Chemical Encyclopedia: Pyrrolizidine alkaloids. xumuk.ru
  49. ↑ Plemenkov, p. 229
  50. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  51. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  52. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  53. ↑ Plemenkov, p. 225
  54. ↑ Aniszewski, p. 95
  55. ↑ Orekhov, p. 80
  56. ↑ 56.0 56.1 56.2 56.3 56.4 56.5 Chemical Encyclopedia: Quinolizidine alkaloids. xumuk.ru
  57. ↑ Saxton, Vol. 1, p. 93
  58. ↑ Aniszewski, p. 98
  59. ↑ Saxton, Vol. 1, p. 91
  60. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  61. ↑ Saxton, Vol. 1, p. 92
  62. ↑ Dewick, p. 310
  63. ↑ Aniszewski, p. 96
  64. ↑ Aniszewski, p. 97
  65. ↑ 65.0 65.1 65.2 Plemenkov, p. 227
  66. ↑ 66.0 66.1 Chemical Encyclopedia: pyridine alkaloids. xumuk.ru
  67. ↑ 67.0 67.1 Aniszewski, p. 107
  68. ↑ 68.0 68.1 Aniszewski, p. 85
  69. ↑ Plemenkov, p. 228
  70. ↑ 70.0 70.1 Hesse, p. 36
  71. ↑ 71.00 71.01 71.02 71.03 71.04 71.05 71.06 71.07 71.08 71.09 71.10 71.11 71.12 71.13 71.14 71.15 71.16 71.17 71.18 71.19 Chemical Encyclopedia: isoquinoline alkaloids. xumuk.ru
  72. ↑ Aniszewski, pp. 77–78
  73. ↑ 73.0 73.1 73.2 73.3 Begley, Alkaloid Biosynthesis
  74. ↑ 74.0 74.1 Saxton, Vol. 3, p. 122
  75. ↑ 75.0 75.1 75.2 Hesse, p. 54
  76. ↑ 76.0 76.1 Hesse, p. 37
  77. ↑ Hesse, p. 38
  78. ↑ 78.0 78.1 78.2 Hesse, p. 46
  79. ↑ 79.0 79.1 79.2 Hesse, p. 50
  80. ↑ 80.0 80.1 80.2 One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  81. ↑ 81.0 81.1 Hesse, p. 47
  82. ↑ Hesse, p. 39
  83. ↑ 83.0 83.1 Hesse, p. 41
  84. ↑ 84.0 84.1 Hesse, p. 49
  85. ↑ Hesse, p. 44
  86. ↑ 86.0 86.1 86.2 Saxton, Vol. 3, p. 164
  87. ↑ 87.0 87.1 Hesse, p. 51
  88. ↑ 88.0 88.1 88.2 Plemenkov, p. 236
  89. ↑ Saxton, Vol. 3, p. 163
  90. ↑ Saxton, Vol. 3, p. 168
  91. ↑ Hesse, p. 52
  92. ↑ Hesse, p. 53
  93. ↑ 93.0 93.1 93.2 93.3 93.4 Plemenkov, p. 241
  94. ↑ Brossi, Vol. 35, p. 261
  95. ↑ Brossi, Vol. 35, pp. 260–263
  96. ↑ 96.0 96.1 Plemenkov, p. 242
  97. ↑ Begley, Cofactor Biosynthesis
  98. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  99. ↑ Chemical Encyclopedia: Quinazoline alkaloids. xumuk.ru
  100. ↑ Aniszewski, p. 106
  101. ↑ 101.0 101.1 Aniszewski, p. 105
  102. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  103. ↑ Plemenkov, pp. 231, 246
  104. ↑ Hesse, p. 58
  105. ↑ Plemenkov, p. 231
  106. ↑ 106.0 106.1 106.2 106.3 Chemical Encyclopedia: Quinoline alkaloids. xumuk.ru
  107. ↑ 107.0 107.1 Aniszewski, p. 114
  108. ↑ Orekhov, p. 205
  109. ↑ Hesse, p. 55
  110. ↑ 110.0 110.1 Plemenkov, p. 232
  111. ↑ Orekhov, p. 212
  112. ↑ Aniszewski, p. 118
  113. ↑ 113.0 113.1 Aniszewski, p. 112
  114. ↑ 114.0 114.1 114.2 114.3 114.4 114.5 Aniszewski, p. 113
  115. ↑ Hesse, p. 15
  116. ↑ Saxton, Vol. 1, p. 467
  117. ↑ Dewick, pp. 349–350
  118. ↑ 118.0 118.1 118.2 Aniszewski, p. 119
  119. ↑ Hesse, p. 29
  120. ↑ Hesse, pp. 23–26
  121. ↑ Saxton, Vol. 1, p. 169
  122. ↑ Saxton, Vol. 5, p. 210
  123. ↑ Hesse, pp. 17–18
  124. ↑ Dewick, p. 357
  125. ↑ 125.0 125.1 Aniszewski, p. 104
  126. ↑ Hesse, p. 72
  127. ↑ Hesse, p. 73
  128. ↑ Dewick, p. 396
  129. ↑ PlantCyc Pathway: ephedrine biosynthesisTemplate:Dead link
  130. ↑ Hesse, p. 76
  131. ↑ 131.0 131.1 Chemical Encyclopedia: colchicine alkaloids. xumuk.ru
  132. ↑ Aniszewski, p. 77
  133. ↑ 133.0 133.1 Hesse, p. 81
  134. ↑ Brossi, Vol. 23, p. 376
  135. ↑ 135.0 135.1 Hesse, p. 77
  136. ↑ Brossi, Vol. 23, p. 268
  137. ↑ Brossi, Vol. 23, p. 231
  138. ↑ 138.0 138.1 138.2 138.3 138.4 138.5 Hesse, p. 82
  139. ↑ Spermine Biosynthesis
  140. ↑ 140.0 140.1 140.2 140.3 140.4 140.5 Plemenkov, p. 243
  141. ↑ Chemical Encyclopedia: Terpenes. xumuk.ru
  142. ↑ Begley, Natural Products: An Overview
  143. ↑ One of the biggest reasons investing in a Singapore new launch is an effective things is as a result of it is doable to be lent massive quantities of money at very low interest rates that you should utilize to purchase it. Then, if property values continue to go up, then you'll get a really high return on funding (ROI). Simply make sure you purchase one of the higher properties, reminiscent of the ones at Fernvale the Riverbank or any Singapore landed property Get Earnings by means of Renting

    In its statement, the singapore property listing - website link, government claimed that the majority citizens buying their first residence won't be hurt by the new measures. Some concessions can even be prolonged to chose teams of consumers, similar to married couples with a minimum of one Singaporean partner who are purchasing their second property so long as they intend to promote their first residential property. Lower the LTV limit on housing loans granted by monetary establishments regulated by MAS from 70% to 60% for property purchasers who are individuals with a number of outstanding housing loans on the time of the brand new housing purchase. Singapore Property Measures - 30 August 2010 The most popular seek for the number of bedrooms in Singapore is 4, followed by 2 and three. Lush Acres EC @ Sengkang

    Discover out more about real estate funding in the area, together with info on international funding incentives and property possession. Many Singaporeans have been investing in property across the causeway in recent years, attracted by comparatively low prices. However, those who need to exit their investments quickly are likely to face significant challenges when trying to sell their property – and could finally be stuck with a property they can't sell. Career improvement programmes, in-house valuation, auctions and administrative help, venture advertising and marketing, skilled talks and traisning are continuously planned for the sales associates to help them obtain better outcomes for his or her shoppers while at Knight Frank Singapore. No change Present Rules

    Extending the tax exemption would help. The exemption, which may be as a lot as $2 million per family, covers individuals who negotiate a principal reduction on their existing mortgage, sell their house short (i.e., for lower than the excellent loans), or take part in a foreclosure course of. An extension of theexemption would seem like a common-sense means to assist stabilize the housing market, but the political turmoil around the fiscal-cliff negotiations means widespread sense could not win out. Home Minority Chief Nancy Pelosi (D-Calif.) believes that the mortgage relief provision will be on the table during the grand-cut price talks, in response to communications director Nadeam Elshami. Buying or promoting of blue mild bulbs is unlawful.

    A vendor's stamp duty has been launched on industrial property for the primary time, at rates ranging from 5 per cent to 15 per cent. The Authorities might be trying to reassure the market that they aren't in opposition to foreigners and PRs investing in Singapore's property market. They imposed these measures because of extenuating components available in the market." The sale of new dual-key EC models will even be restricted to multi-generational households only. The models have two separate entrances, permitting grandparents, for example, to dwell separately. The vendor's stamp obligation takes effect right this moment and applies to industrial property and plots which might be offered inside three years of the date of buy. JLL named Best Performing Property Brand for second year running

    The data offered is for normal info purposes only and isn't supposed to be personalised investment or monetary advice. Motley Fool Singapore contributor Stanley Lim would not personal shares in any corporations talked about. Singapore private home costs increased by 1.eight% within the fourth quarter of 2012, up from 0.6% within the earlier quarter. Resale prices of government-built HDB residences which are usually bought by Singaporeans, elevated by 2.5%, quarter on quarter, the quickest acquire in five quarters. And industrial property, prices are actually double the levels of three years ago. No withholding tax in the event you sell your property. All your local information regarding vital HDB policies, condominium launches, land growth, commercial property and more

    There are various methods to go about discovering the precise property. Some local newspapers (together with the Straits Instances ) have categorised property sections and many local property brokers have websites. Now there are some specifics to consider when buying a 'new launch' rental. Intended use of the unit Every sale begins with 10 p.c low cost for finish of season sale; changes to 20 % discount storewide; follows by additional reduction of fiftyand ends with last discount of 70 % or extra. Typically there is even a warehouse sale or transferring out sale with huge mark-down of costs for stock clearance. Deborah Regulation from Expat Realtor shares her property market update, plus prime rental residences and houses at the moment available to lease Esparina EC @ Sengkang
  144. ↑ Hesse, p. 88
  145. ↑ Dewick, p. 388
  146. ↑ Plemenkov, p. 247
  147. ↑ Никотин. Great Soviet Encyclopedia (1969–1978)
  148. ↑ 148.0 148.1 148.2 Grinkevich, p. 131
  149. ↑ G. A. Spiller Caffeine, CRC Press, 1997 ISBN 0-8493-2647-8
  150. ↑ Template:Cite web
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  155. ↑ Template:Cite webTemplate:Dead link
  156. ↑ Fattorusso, p. 53
  157. ↑ 20 year-old Real Estate Agent Rusty from Saint-Paul, has hobbies and interests which includes monopoly, property developers in singapore and poker. Will soon undertake a contiki trip that may include going to the Lower Valley of the Omo.

    My blog: http://www.primaboinca.com/view_profile.php?userid=5889534
  158. ↑ Aniszewski, p. 13
  159. ↑ Orekhov, p. 11
  160. ↑ Hesse, p.4
  161. ↑ Grinkevich, pp. 122–123
  162. ↑ Orekhov, p. 12
  163. ↑ Fattorusso, p. XVII
  164. ↑ Aniszewski, pp. 110–111
  165. ↑ 165.0 165.1 165.2 165.3 Hesse, p. 116
  166. ↑ 166.0 166.1 Grinkevich, p. 132
  167. ↑ Grinkevich, p. 5
  168. ↑ Grinkevich, pp. 132–134
  169. ↑ Grinkevich, pp. 134–136
  170. ↑ 170.0 170.1 170.2 Plemenkov, p. 253
  171. ↑ Plemenkov, p. 254
  172. ↑ 172.0 172.1 Dewick, p. 19
  173. ↑ Plemenkov, p. 255
  174. ↑ Dewick, p. 305
  175. ↑ Hesse, pp. 91–105
  176. ↑ Aniszewski, p. 142
  177. ↑ Hesse, pp. 283–291
  178. ↑ Aniszewski, pp. 142–143
  179. ↑ W.E. Conner (2009). Tiger Moths and Woolly Bears—behaviour, ecology, and evolution of the Arctiidae. New York: Oxford University Press. pp. 1–10. ISBN 0195327373.
  180. ↑ Hesse, p. 303
  181. ↑ Hesse, pp. 303–309
  182. ↑ Hesse, p. 309
  183. ↑ Dewick, p. 335
  184. ↑ György Matolcsy, Miklós Nádasy, Viktor Andriska Pesticide chemistry, Elsevier, 2002, pp. 21–22 ISBN 0-444-98903-X
  185. ↑ Veselovskaya, p. 75
  186. ↑ Hesse, p. 79
  187. ↑ Veselovskaya, p. 136
  188. ↑ Geoffrey A. Cordell The Alkaloids: Chemistry and Biology. Vol. 56, Elsevier, 2001, p. 8, ISBN 978-0-12-469556-6.
  189. ↑ Veselovskaya, p. 6
  190. ↑ Veselovskaya, pp. 51–52


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