N-Methyltryptamine

N-Methyltryptamine
Clinical data
Other namesNMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
Legal status
Legal status
Identifiers
IUPAC name
  • 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.462
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
Melting point87 to 89 °C (189 to 192 °F)
SMILES
  • CNCCc1c[nH]c2ccccc12
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 checkY
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N checkY
  (verify)

N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.

It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase.[1][2] It is a known component in human urine.[3] 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).[4]

NMT acts as a serotonin receptor agonist and serotonin releasing agent[5] and produces psychoactive and hallucinogenic effects in humans.[6]

Effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.[7] However, it may become active upon combination with a MAOA inhibitor (MAOI).[7]

By vaporization, NMT shows psychoactive activity at 50 to 100 mg, with a duration of 45 to 70 minutes; duration of visual effects is said to be only 15 to 30 seconds. Effects are primarily non-visual.[6][8]

Pharmacology

NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (EC50Tooltip half-maximal effective concentration = 50.7 nM; EmaxTooltip maximal efficacy = 96%).[5] It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor.[5] In contrast to the serotonin 5-HT2A receptor, the drug is not an agonist of the serotonin 5-HT1A receptor.[5]

In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent (EC50 = 22.4 nM).[5] It also releases dopamine and norepinephrine much more weakly (EC50 = 321 nM and 733 nM, respectively; 14- and 33-fold less than for serotonin, respectively).[5]

Legality

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT) [9]

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. ↑ Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences. 26 (5): 274–281. doi:10.1016/j.tips.2005.03.007. PMID 15860375.
  2. ↑ Burchett SA, Hicks TP (August 2006). "The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain". Progress in Neurobiology. 79 (5–6): 223–246. doi:10.1016/j.pneurobio.2006.07.003. PMID 16962229. S2CID 10272684.
  3. ↑ Forsström T, Tuominen J, Karkkäinen J (2001). "Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS". Scandinavian Journal of Clinical and Laboratory Investigation. 61 (7): 547–56. doi:10.1080/003655101753218319. PMID 11763413. S2CID 218987277.
  4. ↑ Ott, J. Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History (1993), ISBN 0-9614234-2-0
  5. 1 2 3 4 5 6 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
  6. 1 2 Shulgin A, Shulgin A (1997). TiHKAL. Berkeley: Transform Press.
  7. 1 2 Foye WO, Lemke TL, Williams DA (2002). "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). p. 439. ISBN 9780683307375.
  8. ↑ Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.
  9. ↑ "Orange Book - List of Controlled Substances and Regulated Chemicals" (PDF). U.S. Department of Justice Diversion Control Division. August 2023. Archived (PDF) from the original on September 6, 2023.
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