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.
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.
|Harmane|| || |
|Harmine|| || || |
|Harmaline|| || |
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.
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.
- ↑ 1.0 1.1 Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof
- ↑ www.amazing-nature.com
- ↑ Stachel, Shawn J; Scott A Stockwell and David L Van Vranken (August 1999). "The fluorescence of scorpions and cataractogenesis". Chemistry & Biology (Cell Press) 6: 531–539. http://www.chembiol.com/content/article/abstract?uid=PIIS1074552199800854. Retrieved 2008-06-17.
- TiHKAL #44
- Beta-carbolines in Coffee
- Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test
|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.|