2-Methyltryptamine


2-Methyltryptamine is a serotonin receptor agonist of the tryptamine family. It shows dramatically reduced activity at serotonin receptors compared to tryptamine and mixed effects in terms of psychedelic-like effects in animals.

Pharmacology

Pharmacodynamics

2-MT shows affinity for the serotonin 5-HT1A and 5-HT2A receptors, with Ki values of 1,095nM and 7,774nM, respectively. These affinities were respectively 34-fold and 3.2-fold lower than those of tryptamine in the same study. It also acts as an agonist of the serotonin 5-HT1A and 5-HT2A receptors, with values of 12,534nM and 4,598nM, respectively. These activational potencies were respectively 14-fold and 19-fold lower than those of tryptamine in the same study.
It does not produce conditioned place preference, self-administration, or changes in locomotor activity in rodents. Findings on whether 2-MT produces the head-twitch response, a behavioral proxy of psychedelic effects, are mixed. In one study, it produced the HTR at a dose of 3mg/kg intraperitoneally, and this was completely blocked by the serotonin 5-HT2A receptor antagonist ketanserin. In another study, both tryptamine and 2-MT did not produce the HTR at a dose of 3mg/kg intraperitoneally.

Chemistry

Derivatives

A number of derivatives of 2-MT are known, including:
  • 2,α-Dimethyltryptamine
  • 2,N,''N-Trimethyltryptamine
  • 2-Methyl-N'',N-diethyltryptamine
  • 5-Methoxy-2,N,''N''-trimethyltryptamine
These drugs were synthesized and tested by Alexander Shulgin. He found that the drugs in this group became orally active but generally produced no or only mild psychedelic effects. Instead, they caused effects like tactile enhancement and auditory distortion, among others.
A few other derivatives, including 2-methyl-DiPT, 2-methyl-iPALT, 2-methyl-5-MeO-DALT, and 2-methyl-5-F-DALT, are also known.
Further derivatives of 2-MT include the following:
EMD-386088 isn't technically a tryptamine but is very similar and is a serotonin 5-HT6 receptor partial agonist as well as having moderate affinity for the serotonin 5-HT3 receptor and acting as a dopamine reuptake inhibitor.
Yet another related compound is 2-HO-NMT, a tryptamine alkaloid.