| Verifiedfields: | verified |
| Watchedfields: | verified |
| Verifiedrevid: | 464372446 |
| Iupac Name: | 2-(1H-Indol-3-yl)-N-methylethan-1-amine |
| Drug Name: | N-Methyltryptamine |
| Legal Us: | Schedule I (isomer of AMT) |
| Cas Number: | 61-49-4 |
| Unii: | 6FRL4L3Z7V |
| Pubchem: | 6088 |
| Chemspiderid: | 5863 |
| Kegg: | C06213 |
| Chebi: | 28136 |
| Chembl: | 348588 |
| Synonyms: | NMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine |
| C: | 11 |
| H: | 14 |
| N: | 2 |
| Smiles: | CNCCc1c[nH]c2ccccc12 |
| Stdinchi: | 1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3 |
| Stdinchikey: | NCIKQJBVUNUXLW-UHFFFAOYSA-N |
| Melting Point: | 87 |
| Melting High: | 89 |
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 and produces psychoactive and hallucinogenic effects in humans.
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[5] However, it may become active upon combination with a MAOA inhibitor (MAOI).[5]
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.[6] [7]
NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (= 50.7nM; = 96%).[8] 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 (= 22.4nM). It also releases dopamine and norepinephrine much more weakly (= 321nM and 733nM, respectively; 14- and 33-fold less than for serotonin, respectively).
In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT) [9]