Chemistry:7-MeO-DMT

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7-MeO-DMT, or 7-OMe-DMT, also known as 7-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family.[1] It is the 7-methoxy derivative of the serotonergic psychedelic dimethyltryptamine (DMT) and is a positional isomer of 5-MeO-DMT, 4-MeO-DMT, and 6-MeO-DMT.[1]

Use and effects

7-MeO-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.[2]

Pharmacology

Pharmacodynamics

In an early study using the isolated rat stomach fundus strip, the drug showed very low serotonin receptor affinity (A2 = 4,677 nM) that was about 56-fold lower than that of 5-MeO-DMT.[3][4][5] However, this assay was subsequently found to be an unreliable predictor of hallucinogenic activity.[6] The receptor in this tissue may correspond to the serotonin 5-HT2B receptor.[7]

In subsequent studies, 7-MeO-DMT bound to the serotonin 5-HT2A receptor (Ki = 5,400–5,440 nM) and had 9- to 59-fold lower affinity than 5-MeO-DMT and 5- to 17-fold lower affinity than DMT.[1][8][9] It showed no detectable affinity for the serotonin 5-HT2C receptor (Ki = >10,000 nM), but did show affinity for the serotonin 5-HT1A receptor (Ki = 1,760 nM).[9] Its affinity for the serotonin 5-HT1A receptor was 160-fold lower than that of 5-MeO-DMT and was 9-fold lower than that of DMT.[9] 7-MeO-DMT has also been assessed at the serotonin 5-HT1E and 5-HT1F receptors (Ki = >10,000 nM and 2,620 nM, respectively).[10]

7-MeO-DMT substitutes for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests.[5] The drug was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL and is not known to have been tested in humans.[3][2] Hence, it is unknown whether 7-MeO-DMT produces psychedelic effects in humans.[3][2]

Chemistry

Analogues

Analogues of 7-MeO-DMT include dimethyltryptamine (DMT), 4-MeO-DMT, 5-MeO-DMT, and 6-MeO-DMT, among others.[2][1]

History

7-MeO-DMT was first described in the scientific literature by at least 1968.[11]

Society and culture

United States

7-MeO-DMT is not an explicitly controlled substance in the United States, but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DMT.[12][13]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. "Nevertheless, substitutions at positions 6 or 7 were reported to reduce or even abolish the binding ability to 5-HT2 receptors. For example, 6-OMe-DMT (35, Ki = 7300 nM) and 7-OMe-DMT (36, Ki = 5400 nM) exhibited reduced affinity compared to that of DMT (Ki = 1200 nM) at [3H]-ketanserin-labeled 5-HT2Rs.124". 
  2. ↑ 2.0 2.1 2.2 2.3 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. 
  3. ↑ 3.0 3.1 3.2 "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews 6 (4): 489–497. 1982. doi:10.1016/0149-7634(82)90030-6. PMID 6757811. 
  4. ↑ "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry 22 (4): 428–432. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  5. ↑ 5.0 5.1 "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology 68 (2): 155–158. 1980. doi:10.1007/BF00432133. PMID 6776558. 
  6. ↑ "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. 
  7. ↑ "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. 
  8. ↑ "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology 145 (3): 291–297. January 1988. doi:10.1016/0014-2999(88)90432-3. PMID 3350047. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=cabb8bfdccd28f358a469865fe8f08afe29d7086. Retrieved 2025-06-18. 
  9. ↑ 9.0 9.1 9.2 "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence 60 (2): 121–132. August 2000. doi:10.1016/s0376-8716(99)00148-9. PMID 10940539. 
  10. ↑ "Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships". The Journal of Pharmacology and Experimental Therapeutics 337 (3): 860–867. June 2011. doi:10.1124/jpet.111.179606. PMID 21422162. 
  11. ↑ "Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines". Life Sciences 7 (5): 267–277. March 1968. doi:10.1016/0024-3205(68)90200-2. PMID 5641719. 
  12. ↑ 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 
  13. ↑ Drug Enforcement Administration (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances". https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances. 



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