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N-Methyltryptamine

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N-Methyltryptamine
NMT structure.svg
Legal status
Legal status
Identifiers
  • 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.462
Chemical and physical data
Formula C11H14N2
Molar mass 174.247 g·mol−1
3D model (JSmol)
Melting point 87 to 89 °C (189 to 192 °F)
  • CNCCc1c[nH]c2ccccc12
  • 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 checkY
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N checkY
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N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common component in human urine. 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).

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 MAOA 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.

Legality

In the United States N-Methyltryptamine is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT)

See also

External links


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