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| Pharmacology | |||||||||||||||||||||||
| 2>
β-Carboline alkaloids are widespread in plants and animals, and frequently act as monoamine oxidase inhibitors (MAOI). As components of the liana Banisteriopsis caapi, the β-carbolines harmine, harmaline, and tetrahydroharmine play a pivotal role in the pharmacology of the indigenous hallucinogenic drug ayahuasca by preventing the breakdown of dimethyltryptamine in the gut by inhibiting monoamine oxidase, thus making it psychoactive upon oral administration. Some β-carbolines, notably tryptoline and pinoline, are formed naturally in the human body. The latter is implicated along with melatonin in the role of the pineal gland in regulating the sleep-wake cycle.[citation needed] The β-carboline can link to cerebral benzodiazepine receptors and induce inverse agonist effect.
[edit] Tags:Reliable Sources,Challenged,Smiles,Molecular Formula,Pyrido,Indole,Heterocycle,Compounds,Alkaloids,Plants,Animals,Monoamine Oxidase Inhibitors,Banisteriopsis Caapi,Harmine,Harmaline,Tetrahydroharmine,Hallucinogenic,Ayahuasca,Dimethyltryptamine,Monoamine Oxidase,Tryptoline,Pinoline,Melatonin,Pineal Gland,Benzodiazepine,Indole Alkaloids,Pyridine,Tryptamine,Ethylamine,Carbon,Saturation,Structural Formula,Och,Ch,Citations,Help, | |||||||||||||||||||||||
| Structure | 2>
β-Carboline belongs to the group of indole alkaloids and consist of pyridine ring that is fused to an indole skeleton.[1] The structure of β-carboline is similar to that of tryptamine, with the ethylamine chain re-connected to the indole ring via an extra carbon atom, to produce a three-ringed structure. The biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines.[2] Different levels of saturation are possible in the third ring, which is indicated here in the structural formula by colouring the optionally double bonds red and blue:
[edit] | Tags: Examples of β-carbolines | 2>
Some of the more important β-carbolines are tabulated by structure below.
Short Name
Red Bond
Blue Bond
R1
R6
R7
Structure
β-Carboline
×
×
H
H
H
Tryptoline
H
H
H
Pinoline
H
OCH3
H
Harmane
×
CH3
H
H
Harmine
×
×
CH3
H
OCH3
Harmaline
×
CH3
H
OCH3
Tetrahydroharmine
CH3
H
H
OCH3
[edit] | Tags: Occurrence in nature | 2>
This article may contain inappropriate or misinterpreted citations that do not verify the text. Please help improve this article by checking for inaccuracies. (help, talk, get involved!) (December 2007)
"There are presently 64 known β-carboline alkaloids dispersed throughout at least eight plant families." The seeds of Peganum harmala (Syrian Rue) are a good source of beta-carbolines. Estimates of the quantity of harmaline in P. harmala seeds range from 0.16% [3] to 5.9% [4]of the dried weight. (As for most plants, yields vary with factors such as sub-species, growing conditions and season of collection.)
As a result of the presence of β-carbolines in the cuticle of scorpions, their skin is known to fluoresce when exposed to certain wavelengths of ultraviolet light such as that produced by a blacklight.[5]
Several β-carbolines have actions opposite to those of benzodiazepines: convulsive, anxiogenic and memory enhancing.[6]
[edit] | Tags: References | 2>
^ The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications. Ratsch, Christian. Park Street Press c. 2005
^ Baiget, Jessica; Llona-Minguez, Sabin; Lang, Stuart; MacKay, Simon P; Suckling, Colin J; Sutcliffe, Oliver B (2011). "Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-bindole-1-carboxylate: Concise synthesis of alangiobussinine"]. Beilstein Journal of Organic Chemistry 7: 1407–11. doi:10.3762/bjoc.7.164. PMC 3201054. PMID 22043251. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3201054.
^ Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (Aug 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal Chim Acta 575 (2): 290–9. doi:10.1016/j.aca.2006.05.093. PMID 17723604.
^ Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. (2010). "beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)". Food Chem Toxicol. 48 (3): 839–43. doi:10.1016/j.fct.2009.12.019. PMID 20036304.
^ Stachel SJ, Stockwell SA, Van Vranken DL (August 1999). "The fluorescence of scorpions and cataractogenesis". Chem. Biol. 6 (8): 531–9. doi:10.1016/S1074-5521(99)80085-4. PMID 10421760.
^ Venault P, Chapouthier G (2007). "From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory". ScientificWorldJournal 7: 204–23. doi:10.1100/tsw.2007.48. PMID 17334612.
[edit] | Tags: External links | 2>
MeSH Beta-Carbolines
TiHKAL #44
TiHKAL in general
Beta-carbolines in Coffee
Farzin D, Mansouri N (July 2006). "Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test". Eur Neuropsychopharmacol 16 (5): 324–8. doi:10.1016/j.euroneuro.2005.08.005. PMID 16183262.
Retrieved from "http://en.wikipedia.org/w/index.php?title=Beta-Carboline&oldid=490149895"
Categories: Beta-CarbolinesEntheogensMonoamine oxidase inhibitorsHidden categories: Articles needing additional references from December 2007All articles needing additional referencesAll articles with unsourced statementsArticles with unsourced statements from July 2008Articles lacking reliable references from December 2007All articles lacking reliable references
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