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.
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]
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 120Script error: No such module "String".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]
Pharmacology
NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (EC50 = 50.7Script error: No such module "String".nM; Emax = 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] In contrast to the serotonin 5-HT2A receptor, 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 = 22.4Script error: No such module "String".nM).[5] It also releases dopamine and norepinephrine much more weakly (EC50 = 321Script error: No such module "String".nM and 733Script error: No such module "String".nM, respectively; 14- and 33-fold less than for serotonin, respectively).[5]
Society and culture
Legal status
In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT).[11]
See also
- N-Ethyltryptamine (NET)
- N,N,-Dimethyltryptamine (DMT)
- Acacia confusa (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)
- Acacia obtusifolia (NMT up to 2/3 alkaloid content)
- Acacia simplicifolia (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet et al. 1976)
- Desmanthus illinoensis (NMT major component seasonally)
References
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External links
- NMT - Isomer Design
- NMT - TiHKAL - Erowid
- NMT - TiHKAL - Isomer Design
- N-Methyltryptamine (NMT) - Trout's Notes
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