N-Methyltryptamine

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N-Methyltryptamine
Systematic (IUPAC) name
2-(1H-Indol-3-yl)-N-methylethanamine
Clinical data
Legal status ?
Identifiers
CAS number 61-49-4 N
ATC code ?
PubChem CID 6088
ChemSpider 5863 YesY
KEGG C06213 YesY
ChEBI CHEBI:28136 YesY
ChEMBL CHEMBL348588 YesY
Chemical data
Formula C11H14N2 
Mol. mass 174.245 g/mol
Physical data
Melt. point 87–89 °C (189–192 °F)
 N (what is this?)  (verify)

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).[4] By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds.[5][6]

NMT has been shown to act as an agonist of the TAAR1, similarly to its relatives tryptamine and N,N-dimethyltryptamine (DMT).[7]

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

  1. ↑ see wikipedia list of psychedlic plants for references
  2. ↑ Tryptophan metabolism
  3. ↑ 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.
  4. ↑ 4.0 4.1 Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams
  5. ↑ Shulgin & Shulgin "TIKHAL" 1997
  6. ↑ Nen 2011 - lecture presented EGA conference, Victoria. 4/12/2011.
  7. ↑ 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. 

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M: PNS

anat (h/r/t/c/b/l/s/a)/phys (r)/devp/prot/nttr/nttm/ntrp

noco/auto/cong/tumr, sysi/epon, injr

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