- Beta-Carboline
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ImageFile=Beta-carboline (small).svg
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IUPACName=9H-pyrido [3,4-b] indole
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Section1= Chembox Identifiers
CASNo=244-63-3
PubChem=64961
SMILES=C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
MeSHName=norharman
Section2= Chembox Properties
Formula=C11H8N2
MolarMass=168.19462
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Section3= Chembox Hazards
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Autoignition= β-Carboline (9"H"-pyrido [3,4-"b"]indole ) is an organicamine that is the prototype of a class of compounds known as β-"carbolines".Pharmacology
β-carboline
alkaloid s are widespread inplants andanimal s, and frequently act asmonoamine oxidase inhibitor s (MAOI). As components of the liana "Banisteriopsis caapi ", the β-carbolinesharmine ,harmaline , andtetrahydroharmine play a pivotal role in the pharmacology of thepsychedelic brewayahuasca . Some β-carbolines, notablytryptoline andpinoline , are formed naturally in the human body. The latter is implicated along withmelatonin in the role of thepineal gland in regulating the sleep-wake cycle.Fact|date=July 2008United States
Patent Number 5591738 describes a method for treating various chemical dependencies via the administration of beta-carbolines. [http://www.freepatentsonline.com/5591738.html Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof] ]tructure
The structure of β-carboline is similar to that of
tryptamine , with theethylamine chain re-connected to theindole ring via an extracarbon atom, to produce a three-ringed structure. Indeed, biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines. Different levels of saturation are possible in the third ring, which is indicated here in thestructural formula by colouring the optionally double bonds red and blue:Examples of β-carbolines
Some of the more important β-carbolines are tabulated by structure below.
Occurrence in nature
"There are presently 64 known .beta.-carboline alkaloids dispersed throughout at least eight plant families." [http://www.freepatentsonline.com/5591738.html Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof] ] The seeds of "
Peganum harmala " (Syrian Rue) are a good source of beta-carbolines, since they contain about 2-6% alkaloids, most of which is harmaline. [ [http://www.amazing-nature.com/-i-43.html www.amazing-nature.com] ] Rs|date=December 2007ee also
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Harmala alkaloid
*Tryptamine External links
* [http://www.erowid.org/library/books_online/tihkal/tihkal44.shtml TiHKAL #44]
* [http://www.erowid.org/library/books_online/tihkal TiHKAL] in general
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* [http://www.biopsychiatry.com/coffee-maoi.htm Beta-carbolines in Coffee]
* [http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=16183262&dopt=AbstractPlus Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test]References
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