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β-Carboline

Names
IUPAC name 9H-β-carboline
Other names 9H-pyridoindole
Identifiers
CAS Number	244-63-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:109895
ChEMBL	ChEMBL275224
ChemSpider	58486
ECHA InfoCard	100.005.418
MeSH	norharman
PubChem CID	64961
CompTox Dashboard (EPA)	DTXSID2021070
InChI InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13HKey: AIFRHYZBTHREPW-UHFFFAOYSA-N InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13HKey: AIFRHYZBTHREPW-UHFFFAOYAG
SMILES c2cncc3nc1ccccc1c23
Properties
Chemical formula	C11H8N2
Molar mass	168.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

β-Carboline (9H-pyridoindole) 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 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. The β-carboline can link to cerebral benzodiazepine receptors and induce inverse agonist effect.

United States Patent Number 5591738 describes a method for treating various chemical dependencies via the administration of beta-carbolines.

Structure

β-Carbolines belong to the group of Indole alkaloids. They consist of an indole skeleton and various side chains. 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	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	HH	OCH3

Occurrence in nature

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"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, since they contain about 2-6% alkaloids, most of which is harmaline.

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.

Several β-carbolines have actions opposite to those of benzodiazepines: convulsive, anxiogenic and memory enhancing.

See also

• Harmala alkaloid
• Tryptamine

References

1. ^ Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof
2. The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications. Ratsch, Christian. Park Street Press c. 2005
3. www.amazing-nature.com
4. Stachel, Shawn J (1999). "The fluorescence of scorpions and cataractogenesis". Chemistry & Biology. 6. Cell Press: 531–539. doi:10.1016/S1074-5521(99)80085-4. PMID 10421760. Retrieved 2008-06-17. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
5. 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

External links

• TiHKAL #44
• TiHKAL in general
• Beta-Carbolines at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
• Beta-carbolines in Coffee
• Farzin D, Mansouri N (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. {{cite journal}}: Unknown parameter |month= ignored (help)

• Beta-Carbolines
• Entheogens
• Monoamine oxidase inhibitors