Tryptamines, Beta-carbolines and You



Tryptamines and beta-carbolines are two classes of psychoactive indoles found in plants and animals (1). They have been implicated in a host of neurological functions and display a wide range of neurological activity, which is dependent on their molecular configurations (2). A subgroup of (beta)-carbolines found in some plants are known as the harmala alkaloids; e.g. harmaline in Peganum harmala or Banisteriopsis caapi. Some beta-carbolines have been detected in the tissues and fluids of mammals, including humans, where they are thought to be produced from endogenous tryptamines such as serotonin, 5-methoxy-tryptamine and tryptamine itself. Psychoactive methylated tryptamines such as dimethyltryptamine (DMT), 5-methoxy-dimethyltryptamine (5-MeO-DMT) and 5-hydroxy-dimethyltryptamine (bufotenine) and have been detected in normal human beings as well (3,4,5), though their biological purpose remains a mystery.beta carboline

The psychoactive indoles are interesting not only for their exogenously induced effects on the human mind, but also for their natural occurrence in humans. In the early 1950's, Osmond and Smythies, in their transmethylation hypothesis, proposed endogenous 'schizotoxins' to be responsible for the symptoms characteristic of hallucinatory psychoses, and initiated an era of search for the chemical basis of undesirable states of mind (6). This search was later confounded by the fact that these substances were also found in otherwise normal humans, in addition to many of the other animals in the scientific barnyard. At that time, the psychedelics were commonly referred to as 'psychotomimetics' and 'models for psychosis', and it was difficult to rationalize a normal function for an endogenous psychedelic. Unfortunately, the idea of normal dreaming did not occur to the early pioneers as a possible function for the natural occurrence of endogenous psychedelic substances (7,8).

The Tryptamines Serotonin, melatonin, bufotenine, DMT, 5-MeO-DMT, and tryptamine are well known examples of this group. They primarily originate from tryptophan, an essential amino acid obtained through the diet. All of these tryptamines interact within the central nervous system. DMT is a very potent psychedelic chemical when smoked or injected, but is orally inactive. The onset of its effects are known to be extremely fast, brief and intense. One could say that DMT evokes a transient psychedelic test pattern, exploding with color imagery. 5-MeO-DMT shares similar properties, but is often devoid of visual imagery at effective doses. Its effects have been described as primarily emotive. Bufotenine shares similar properties with these two, especially in terms of a fast onset and short duration of intense action. However, at effective doses, any psychoactivity of interest is essentially lost in the physiological noise it elicits through the serotonergic system. Early reports on the effects of bufotenine in humans clearly indicate its psychoactivity (9), though its polar quality apparently hinders significant passage into the brain. Perhaps the psychoactivity of bufotenine is actually due to its enzymatic conversion to 5-MeO-DMT.