Article · Wikipedia archive · Last revised Jun 11, 2026

N-Methyltryptamine

N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

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N-Methyltryptamine
Clinical data
Other namesNMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
Routes of
administration		Smoking, oral (with an MAOITooltip monoamine oxidase inhibitor)123
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of actionSeconds to minutes123
Identifiers
  • 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)
  • 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
  (verify)

N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase.45 It is a known component of human urine.6 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).7

NMT acts as a serotonin receptor agonist and serotonin releasing agent8 and is said to produce hallucinogenic effects in humans.123

Use and effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.9

According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.10 On the other hand, according to reports given to Alexander Shulgin and by others, NMT is active via non-oral routes.123 It has been said to produce psychedelic effects at doses of 50 to 120 mg by smoking or vaporization, with a duration of seconds to minutes.123 Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects.123

NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI).23

Interactions

Pharmacology

Pharmacodynamics

NMT activities
Target Affinity (Ki, nM)
5-HT1A IA
5-HT2A 51 (EC50Tooltip half-maximal effective concentration)
96% (EmaxTooltip maximal efficacy)
SERT 22a (EC50)
NETTooltip Norepinephrine transporter 733a (EC50)
DATTooltip Dopamine transporter 321a (EC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Neurotransmitter release. Sources: 8

NMT is known to act as a potent serotonin 5-HT2A receptor full agonist.8 It has been reported to be inactive in activating the β-arrestin2 pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor.811 The drug does not seem to be an agonist of the serotonin 5-HT1A receptor.8 On the other hand, it is also a serotonin receptor agonist in the rat uterus and stomach strip.1213

In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent.8 It also releases dopamine and norepinephrine much more weakly (14- and 33-fold less than for serotonin, respectively).8

NMT has also been evaluated for binding affinity at the sigma σ1 and sigma σ2 receptors.14 It's affinity towards both sigma receptors is intermediate between the unmethylated tryptamine and the fully dimethylated DMT.14

Pharmacokinetics

NMT undergoes oxidative deamination by monoamine oxidase (MAO), particularly MAO-A, which preferentially metabolizes serotonin and tryptamine derivatives. The intermediate methylation state of NMT makes it a substrate for further N-methylation to DMT by amine N-methyltransferase (INMT).

Chemistry

Synthesis

The chemical synthesis of NMT has been described.1

Analogues

Analogues of NMT include N-ethyltryptamine (NET), methylethyltryptamine (MET), and dimethyltryptamine (DMT), among others.1

Natural occurrence

NMT is naturally occurring in Acacia species like Acacia confusa (1.63%; Buchanan et al., 2007), Acacia obtusifolia (up to two-thirds of total alkaloid content), and Acacia simplicifolia (A. simplex; 1.44% in bark, 0.29% twigs; Pouet et al., 1976) and Desmanthus illinoensis (major component seasonally).

History

NMT was encountered as a novel designer drug by 2014.15

Society and culture

Canada

NMT is not a controlled substance in Canada.16

United States

In the United States, NMT is considered a schedule 1 controlled substance as an positional isomer of α-methyltryptamine (AMT).17

See also

See also

References

References

  1. Shulgin A, Shulgin A (1997). TiHKAL: The Continuation. Berkeley: Transform Press. To my knowledge there have been no reports of oral activity of NMT, although its wide availability from botanic sources has encouraged some explorers to assay it. I have had one report that the smoking of 50–100 mg gave visuals that lasted for maybe 15 seconds.
  2. Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 (PDF). Retrieved 15 April 2025.{{cite conference}}: CS1 maint: deprecated archival service (link)
  3. Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.
  4. 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.
  5. 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.
  6. 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.
  7. Ott, Jonathan (1996). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company. ISBN 978-0-9614234-8-3.
  8. 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.
  9. Foye WO, Lemke TL, Williams DA (2002). "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). Lippincott Williams & Wilkins. p. 439. ISBN 9780683307375.
  10. Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. N-Monoalkyltryptamines resemble the unsubstituted tryptamines in being good substrates for amine oxidases (Erspamer, 1955), a property which is reflected in their relatively poor hallucinogenic activity as compared to their N,N-dialkyl analogues. Thus, neither tryptamine nor its N-methyl derivative, both of which are oxidatively deaminated in rats to free (and conjugated) indole-3-acetic acids to the extent of 84·6 and 35·7 per cent respectively, produce behavioural changes in animals or man, whereas N,N-dimethyltryptamine, which is but little affected by amine oxidases, is a potent hallucinogen.
  11. Schmid CL, Bohn LM (October 2010). "Serotonin, But Not N-Methyltryptamines, Activates the Serotonin 2A Receptor Via a β-Arrestin2/Src/Akt Signaling Complex In Vivo". The Journal of Neuroscience. 30 (40): 13513–13524. doi:10.1523/JNEUROSCI.1665-10.2010. ISSN 0270-6474. PMC 3001293. PMID 20926677.
  12. Barlow RB, Khan I (March 1959). "Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations". Br J Pharmacol Chemother. 14 (1): 99–107. doi:10.1111/j.1476-5381.1959.tb00934.x. PMC 1481812. PMID 13651585.
  13. Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
  14. Fontanilla D, Johannessen M, Hajipour AR, Cozzi NV, Jackson MB, Ruoho AE (February 2009). "The Hallucinogen N,N -Dimethyltryptamine (DMT) Is an Endogenous Sigma-1 Receptor Regulator". Science. 323 (5916): 934–937. doi:10.1126/science.1166127. ISSN 0036-8075. PMC 2947205. PMID 19213917.
  15. "NMT (N-Метилтриптамин)". АИПСИН (in Russian). Retrieved 2 January 2026.
  16. "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  17. "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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