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N-Methyltryptamine

Clinical data
Other names	NMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine
Legal status
Legal status	US: Schedule I (isomer of AMT)
Identifiers
IUPAC name 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number	61-49-4
PubChem CID	6088
ChemSpider	5863
UNII	6FRL4L3Z7V
KEGG	C06213
ChEBI	CHEBI:28136
ChEMBL	ChEMBL348588
CompTox Dashboard (EPA)	DTXSID70209846
ECHA InfoCard	100.000.462
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol
3D model (JSmol)	Interactive image
Melting point	87 to 89 °C (189 to 192 °F)
SMILES CNCCc1cc2ccccc12
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 Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N
(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. It is a known 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).

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

Effects

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 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.

Pharmacology

NMT is known to act as a potent serotonin 5-HT_2A receptor full agonist (EC₅₀Tooltip half-maximal effective concentration = 50.7 nM; E_maxTooltip maximal efficacy = 96%). 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-HT_2A receptor. In contrast to the serotonin 5-HT_2A receptor, the drug is not an agonist of the serotonin 5-HT_1A receptor.

In addition to its serotonin 5-HT_2A receptor agonism, NMT is a potent serotonin releasing agent (EC₅₀ = 22.4 nM). 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).

Legality

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

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. ^ 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. ^ Shulgin A, Shulgin A (1997). TiHKAL. Berkeley: Transform Press.
7. ^ 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.

External links

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

• 5-HT2A agonists
• Biased ligands
• Experimental hallucinogens
• Psychedelic tryptamines
• Serotonin receptor agonists
• Serotonin releasing agents
• Tryptamine alkaloids