Chemistry:4-Methyl-DMT

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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

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. ↑ 1.0 1.1 1.2 1.3 1.4 "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". J Med Chem 27 (1): 41–45. January 1984. 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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol 86 (3–4): 453–459. January 1983. doi:10.1016/0014-2999(83)90196-6. PMID 6572591. 
  3. ↑ 3.0 3.1 3.2 3.3 "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. June 2011. doi:10.1124/jpet.111.179606. PMID 21422162. 
  4. ↑ 4.0 4.1 4.2 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  5. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. Retrieved 1 February 2025. 
  6. ↑ "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr 146: 74–91. 1994. PMID 8742795. https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79. 
  7. ↑ "Serotonin receptor binding affinities of tryptamine analogues". J Med Chem 22 (4): 428–432. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  8. ↑ "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences 35 (13): 1343–1348. September 1984. doi:10.1016/0024-3205(84)90390-4. PMID 6482656. 
  9. ↑ "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". Br J Pharmacol 112 (1): 323–331. May 1994. doi:10.1111/j.1476-5381.1994.tb13072.x. PMID 8032658. 
  10. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  11. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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