beta-Carboline
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| Beta-Carboline | |
|---|---|
| |
| IUPAC name | 9H-pyrido[3,4-b]indole |
| Identifiers | |
| CAS number | |
| PubChem | |
| MeSH | |
| SMILES | C1=CC=C2C(=C1)C3=C(N2)C=NC=C3 |
| Properties | |
| Molecular formula | C11H8N2 |
| Molar mass | 168.19462 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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β-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as β-carbolines.
Pharmacology
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 psychedelic brew ayahuasca. 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.
United States Patent Number 5591738 describes a method for treating various chemical dependencies via the administration of beta-carbolines.[1]
Structure
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. 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 the structural 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.
| Short Name | R1 | R6 | R7 | Structure | ||
|---|---|---|---|---|---|---|
| β-Carboline | | |||||
| Tryptoline |  | |||||
| Pinoline |  | |||||
| Harmane | | | |  | ||
| Harmine | | | |  | ||
| Harmaline | | |  | |||
| Tetrahydroharmine | |  |
Occurrence in nature
| This article or section may contain inappropriate or misinterpreted citations that do not verify the text. Please help improve this article by checking for inaccuracies. (December 2007) (help, talk, get involved!) |
"There are presently 64 known .beta.-carboline alkaloids dispersed throughout at least eight plant families."[1] 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.[1]Template:Rs
See also
External links
- TiHKAL #44
- TiHKAL in general
- MeSH Beta-Carbolines
- Beta-carbolines in Coffee
- Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test
References
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
