Beta-Carboline

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.Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof
==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	HH 	OCH3	
==Occurrence in nature==
There are presently sixty-four 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.www.amazing-nature.com
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.
==References==
==External links==
* TiHKAL #44
* Beta-carbolines in Coffee
* Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test
Category:Entheogens