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N-Methyltryptamine

Chemical compound From Wikipedia, the free encyclopedia

N-Methyltryptamine
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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.

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It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase.[1][2] It is a known component in human urine.[3] 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).[4]

NMT acts as a serotonin receptor agonist and serotonin releasing agent[5] and is said to produce hallucinogenic effects in humans.[6][7][8]

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Effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[9]

Per Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.[10] On the other hand, according to Alexander Shulgin and others, NMT is active via non-oral routes.[6][7][8] 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.[6][7][8] Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.[6][7][8]

NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).[7][8]

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Pharmacology

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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%).[5] 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.[5] The drug is not an agonist of the serotonin 5-HT1A receptor.[5]

In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent (EC50 = 22.4 nM).[5] 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).[5]

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Society and culture

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT).[11]

See also

References

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