N-Methyltryptamine

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

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[3] However, it may become active upon combination with a MAOA inhibitor (MAOI).[3] 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.[4][5]


See also

References

  1. Tryptophan metabolism
  2. 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.
  3. 3.0 3.1 Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams
  4. Shulgin & Shulgin "TIKHAL" 1997
  5. Nen 2011 - lecture presented EGA conference, Victoria. 4/12/2011.

External links