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Beta-Carboline

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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. 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.[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.

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
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

Occurrence in nature

There are presently sixty-four known β-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.[2]

As a result of the presence of Beta-carbolines in the cuticle of Scorpions, they are known to glow when exposed to certain wavelengths of ultraviolet light such as that produced by a blacklight.[3]

References

External links

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This page uses content from the English Wikipedia. The original article was at Beta-Carboline. The list of authors can be seen in the page history.

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