4-Methyl-DMT

4-Methyl-DMT
Clinical data
Other names4-Me-DMT; 4-Methyl-N,N-dimethyltryptamine; 4,N,N-Trimethyltryptamine; 4,N,N-TMT; 4-TMT
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N,N-dimethyl-2-(4-methyl-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • CC1=C2C(=CC=C1)NC=C2CCN(C)C
  • InChI=1S/C13H18N2/c1-10-5-4-6-12-13(10)11(9-14-12)7-8-15(2)3/h4-6,9,14H,7-8H2,1-3H3
  • Key:SJLWCURJFQWOAR-UHFFFAOYSA-N

4-Methyl-DMT, or 4-Me-DMT, also known as 4-methyl-N,N-dimethyltryptamine or as 4,N,N-trimethyltryptamine (4,N,N-TMT or 4-TMT), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and psilocin (4-HO-DMT).[1][2][3]

Use and effects

4-Methyl-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[4] Its dose in humans is unknown.[2]

The related drug 4-methyl-AMT has shown mixed findings in terms of hallucinogenic effects in humans and is clearly less potent than α-methyltryptamine (AMT) in such regards.[4][5][6]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

4-Methyl-DMT showed affinity for the serotonin receptors in the isolated rat stomach fundus strip (A2 = 141 nM).[1] Its affinity for these receptors was 7-fold higher than that of dimethyltryptamine (DMT), roughly the same as that of psilocin (4-HO-DMT), and about 60% of that of 5-MeO-DMT.[1][7] However, this assay was subsequently found to be an unreliable predictor of hallucinogenic activity.[8] The receptor in this tissue may correspond to the serotonin 5-HT2B receptor.[9]

In other studies, 4-methyl-DMT was assessed and showed affinity for the serotonin 5-HT1E receptor (Ki = 470 nM) and for the serotonin 5-HT1F receptor (Ki = 198 nM).[3] These affinities were similar to but slightly lower than those of DMT (Ki = 300 nM and 130 nM, respectively).[3]

Like DMT and 5-MeO-DMT, 4-methyl-DMT fully substituted for the psychedelic drug DOM in rodent drug discrimination tests.[2] It was a little more than twice as potent as DMT in this assay but was about half as potent as 5-MeO-DMT.[2] Similarly to diethyltryptamine (DET) and dipropyltryptamine (DPT), 4-methyl-DMT produced behavioral disruption at higher doses.[2]

Chemistry

Synthesis

The chemical synthesis of 4-methyl-DMT has been described.[1]

Analogues

Analogues of 4-methyl-DMT include dimethyltryptamine (DMT), psilocin (4-HO-DMT), 4-fluoro-DMT, 4-MeO-DMT, 4-MeO-DET, 1-methyl-DMT, 2-methyl-DMT, 4-methyl-AMT, 4-methyl-AET, 5-methyl-DMT, 6-methyl-DMT, 7-methyl-DMT, and RS134-49 (4-methyl-THPI), among others.[4]

History

4-Methyl-DMT was first described in the scientific literature by Richard Glennon and colleagues by 1983.[2][1][3]

Society and culture

Canada

4-Methyl-DMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[10]

United States

4-Methyl-DMT is not an explicitly controlled substance in the United States.[11] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ^ a b c d e Glennon RA, Jacyno JM, Young R, McKenney JD, Nelson D (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". J Med Chem. 27 (1): 41–45. doi:10.1021/jm00367a008. PMID 6581313. [...] the affinity of isoDMT (7a) was compared with that of DMT (1; pA2 = 6.006). [...] (8) A PA2 value has not been previously reported for 4,N,N-trimethyltryptamine (4-Me-DMT) but was determined, during the course of this study, to be 6.85 (±0.26); Schild slope = 0.93 (±0.21), n = 4. [...] Experimental Section [...] 4,N,N-Trimethyltryptamine Hydrogen Oxalate. [...]
  2. ^ a b c d e f Glennon RA, Young R, Jacyno JM, Slusher M, Rosecrans JA (January 1983). "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol. 86 (3–4): 453–459. doi:10.1016/0014-2999(83)90196-6. PMID 6572591.
  3. ^ a b c d Klein MT, Dukat M, Glennon RA, Teitler M (June 2011). "Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships". J Pharmacol Exp Ther. 337 (3): 860–867. doi:10.1124/jpet.111.179606. PMC 3101003. PMID 21422162.
  4. ^ a b c Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  5. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
  6. ^ Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
  7. ^ Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". J Med Chem. 22 (4): 428–432. doi:10.1021/jm00190a014. PMID 430481.
  8. ^ Nichols DE, Schooler D, Yeung MC, Oberlender RA, Zabik JE (September 1984). "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences. 35 (13): 1343–1348. doi:10.1016/0024-3205(84)90390-4. PMID 6482656.
  9. ^ Baxter GS, Murphy OE, Blackburn TP (May 1994). "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". Br J Pharmacol. 112 (1): 323–331. doi:10.1111/j.1476-5381.1994.tb13072.x. PMC 1910288. PMID 8032658.
  10. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  11. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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