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N-Methyltryptamine

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1903928

N-Methyltryptamine

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N-Methyltryptamine

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 is said to produce hallucinogenic effects in humans.

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.

According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. On the other hand, according to Alexander Shulgin and others, NMT is active via non-oral routes. It has been said to produce psychedelic effects at doses of 50 to 120 mg by smoking or vaporization, with a duration of seconds to minutes. Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.

NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).

NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (EC50Tooltip half-maximal effective concentration = 50.7 nM; EmaxTooltip maximal efficacy = 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. 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 = 22.4 nM). It also releases dopamine and norepinephrine much more weakly (EC50 = 321 nM and 733 nM, respectively; 14- and 33-fold less than for serotonin, respectively).

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