N-Methyltryptamine
Chemical compound
From Wikipedia, the free encyclopedia
N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.
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| Other names | NMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152 |
| Routes of administration | Smoking, oral (with an MAOI)[1][2][3] |
| Drug class | Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Duration of action | Seconds to minutes[1][2][3] |
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| ECHA InfoCard | 100.000.462 |
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| Formula | C11H14N2 |
| Molar mass | 174.247 g·mol−1 |
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| Melting point | 87 to 89 °C (189 to 192 °F) |
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It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase.[4][5] It is a known component of human urine.[6] 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).[7]
NMT acts as a serotonin receptor agonist and serotonin releasing agent[8] and is said to produce hallucinogenic effects in humans.[1][2][3]
Use and effects
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[9]
According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.[10] On the other hand, according to reports given to Alexander Shulgin and by others, NMT is active via non-oral routes.[1][2][3] 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.[1][2][3] Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.[1][2][3]
NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).[2][3]
Interactions
Pharmacology
Pharmacodynamics
NMT is known to act as a potent serotonin 5-HT2A receptor full agonist.[8] It has been reported to be inactive in activating the β-arrestin2 pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor.[8][11] The drug does not seem to be an agonist of the serotonin 5-HT1A receptor.[8]
In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent.[8] It also releases dopamine and norepinephrine much more weakly (14- and 33-fold less than for serotonin, respectively).[8]
NMT has also been evaluated for binding affinity at the sigma σ1 and sigma σ2 receptors.[12] It's affinity towards both sigma receptors is intermediate between the unmethylated tryptamine and the fully dimethylated DMT.[12]
Pharmacokinetics
NMT undergoes oxidative deamination by monoamine oxidase (MAO), particularly MAO-A, which preferentially metabolizes serotonin and tryptamine derivatives. The intermediate methylation state of NMT makes it a substrate for further N-methylation to DMT by amine N-methyltransferase (INMT).
Chemistry
Synthesis
The chemical synthesis of NMT has been described.[1]
Analogues
Analogues of NMT include N-ethyltryptamine (NET), methylethyltryptamine (MET), and dimethyltryptamine (DMT), among others.[1]
Natural occurrence
NMT is naturally occurring in Acacia species like Acacia confusa (1.63%; Buchanan et al., 2007), Acacia obtusifolia (up to two-thirds of total alkaloid content), and Acacia simplicifolia (A. simplex; 1.44% in bark, 0.29% twigs; Pouet et al., 1976) and Desmanthus illinoensis (major component seasonally).
History
NMT was encountered as a novel designer drug by 2014.[13]
Society and culture
Legal status
Canada
NMT is not a controlled substance in Canada.[14]
United States
In the United States, NMT is considered a schedule 1 controlled substance as an positional isomer of α-methyltryptamine (AMT).[15]