N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants. It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a known component in human urine. NMT is an alkaloid derived from L -tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT). NMT acts as a serotonin receptor agonist and serotonin releasing agent and produces psychoactive and hallucinogenic effects in humans.

Effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. However, it may become active upon combination with a MAOA inhibitor (MAOI). By vaporization, NMT shows psychoactive activity at 50 to 100 mg, with a duration of 45 to 70minutes; duration of visual effects is said to be only 15 to 30 seconds. Effects are primarily non-visual.

Pharmacology

NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (EC50 = 50.7nM; Emax = 96%). It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor. In contrast to the serotonin 5-HT2A receptor, the drug is not an agonist of the serotonin 5-HT1A receptor. In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent (EC50 = 22.4nM). It also releases dopamine and norepinephrine much more weakly (EC50 = 321nM and 733nM, respectively; 14- and 33-fold less than for serotonin, respectively).

Legality

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT)