N-Methyltryptamine
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N-Methyltryptamine
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| Systematic (IUPAC) name | |
| 2-(1H-Indol-3-yl)-N-methylethanamine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 61-49-4  |
| ATC code | ? |
| PubChem | CID 6088 |
| ChemSpider | 5863  |
| KEGG | C06213 |
| ChEBI | CHEBI:28136 |
| ChEMBL | CHEMBL348588 |
| Chemical data | |
| Formula | C11H14N2 |
| Mol. mass | 174.245 g/mol |
| SMILES | eMolecules & PubChem |
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| Physical data | |
| Melt. point | 87–89 °C (189–192 °F) |
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N-Methyltryptamine (NMT), or methyltryptamine, is a member of the tryptamine chemical class. It is an alkaloid, probably derived from L-tryptophan, that has been found in the bark, shoots and leaves of several plant species, 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).[1] It is also synthesized in the human body as a metabolic endproduct of the amino acid L-tryptophan.[2] It was found to be a natural trace component in human urine.[3]
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[4] However, it may become active upon combination with a MAOA inhibitor (MAOI).[5] By vaporization NMT shows activity at 50-100mg, with a duration of 45-70 minutes; duration of visual effects 15-30 seconds.[6][7]
NMT has been shown to act as an agonist of the TAAR1, similarly to its relatives tryptamine and N,N-dimethyltryptamine (DMT).[8]
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
- ^ see wikipedia list of psychedlic plants for references
- ^ Tryptophan metabolism
- ^ Scand J Clin Lab Invest. 2001;61(7):547-56. Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Forsström T, Tuominen J, Karkkäinen J.
- ^ Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams
- ^ Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams
- ^ Shulgin & Shulgin "TIKHAL" 1997
- ^ Nen 2011 - lecture presented EGA conference, Victoria. 4/12/2011.
- ^ Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences 26 (5): 274–81. doi:10.1016/j.tips.2005.03.007. PMID 15860375. http://linkinghub.elsevier.com/retrieve/pii/S0165-6147(05)00079-9.
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