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β-carboline alkaloids are widespread in plants and animals, and frequently act as monoamine oxidase inhibitors. As components of 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 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 saturationThe term saturation can refer to the following: In chemistry, saturation has a number of meanings. In color theory, saturation refers to the intensity of a specific hue. Saturation is also a coordinate in the HSV color space. See also: hue. An atmospheric are possible in the third ring, which is indicated here in the structural formulaMany chemical compounds, especially hydrocarbons, can exist in different geometric configurations. A structural formula represents the arrangements of atoms in a way that a chemical formula cannot. One of the advantages with structural formulae is the abi by colouring the optionally double bonds red and blue. Some of the more important β-carbolines are tabulated by structure below.
| Short Name | ? | ? | R1 | R6 | R7 |
|---|---|---|---|---|---|
| β-carboline | × | × | |||
| tryptoline | |||||
| pinoline | OCH3 | ||||
| harman | × | × | CH3 | ||
| harmine | × | × | CH3 | OCH3 | |
| harmaline | × | CH3 | OCH3 | ||
| tetrahydroharmine | CH3 | OCH3 |