N-Methyltryptamine

N-Methyltryptamine

Systematic (IUPAC) name
2-(1H-Indol-3-yl)-N-methylethanamine
Identifiers
CAS Number	61-49-4 N
PubChem	CID: 6088
ChemSpider	5863 Y
KEGG	C06213 Y
ChEBI	CHEBI:28136 Y
ChEMBL	CHEMBL348588 Y
Chemical data
Formula	C11H14N2
Molecular mass	174.245 g/mol
SMILES c1cccc2c1c(cn2)CCNC
InChI InChI=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 Y Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N Y
Physical data
Melting point	87 to 89 °C (189 to 192 °F)
NY (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). It is also synthesized in the human body as a metabolic endproduct of the amino acid L-tryptophan. It was found to be a natural trace component in human urine.

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. However, it may become active upon combination with a MAO_A inhibitor (MAOI). By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. Effects are primarily non-visual.

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)

External links

• NMT Entry in TIHKAL
• NMT Entry in TiHKAL • info