Chemistry:5-MeO-MET

From HandWiki

5-MeO-MET, also known as 5-methoxy-N-methyl-N-ethyltryptamine, is a serotonin receptor modulator, putative serotonergic psychedelic, and relatively rare designer drug of the tryptamine family related to psychedelic drugs like methylethyltryptamine (MET) and 5-MeO-DMT.[1][2][3][4][5]

Use and effects

5-MeO-MET was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[6] Relatedly, its properties, such as dose and duration, and its effects were not described.[6]

Interactions

Pharmacology

Pharmacodynamics

Early studies found 5-MeO-MET to be more potent in animal behavioral tests than 5-MeO-DMT.[2][7] Subsequent studies confirmed that 5-MeO-MET interacts with serotonin receptors similarly to other psychedelic tryptamines.[8][9] A more modern study found that 5-MeO-MET is a potent serotonin 5-HT1A receptor ligand and serotonin 5-HT2A receptor agonist and produces the head-twitch response, a behavioral proxy of psychedelics, in rodents.[1][10] Its activities were of similar potency as 5-MeO-DMT.[1]

Chemistry

Analogues

Analogues of 5-MeO-MET include methylethyltryptamine (MET), 4-HO-MET (metocin), 4-AcO-MET (metacetin), 4-PrO-MET, 5-HO-MET, bretisilocin (5-fluoro-MET), 7F-5-MeO-MET, 5-MeO-DMT, 5-MeO-DET, 5-MeO-MPT, 5-MeO-EPT, 5-MeO-MALT, and 5-MeO-MiPT, among others.

History

5-MeO-MET was first synthesized and limitedly studied in the 1960s.[2][7][8] The drug was first identified on the illicit market in June 2012 in Sweden.[11] It was made illegal in Norway in 2013.[12]

Society and culture

Canada

5-MeO-MET is not a controlled substance in Canada as of 2025.[13]

Sweden

5-MeO-MET is a controlled substance in Sweden.[14]

United States

5-MeO-MET is not an explicitly controlled substance in the United States.[15] 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 "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry 29 (8): 2346–2358. August 2024. doi:10.1038/s41380-024-02506-8. PMID 38486047. 
  2. ↑ 2.0 2.1 2.2 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "Compounds of interest which have not been tested in man include 5-methoxy-N-ethyl-N-methyltryptamine, which is more potent than the N,N-dimethyl analogue in behavioural tests in rodents (Gessner and others, 1968), [...]" 
  3. ↑ "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. 2017. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. 
  4. ↑ "Something New about Something Old: A 10-Year Follow-Up on Classical and New Psychoactive Tryptamines and Results of Analysis". Journal of Psychoactive Drugs 49 (4): 297–305. 2017. doi:10.1080/02791072.2017.1320732. PMID 28569652. 
  5. ↑ "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences 21 (23): 9279. December 2020. doi:10.3390/ijms21239279. PMID 33291798. 
  6. ↑ 6.0 6.1 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. 
  7. ↑ 7.0 7.1 "Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines". Life Sciences 7 (5): 267–77. March 1968. doi:10.1016/0024-3205(68)90200-2. PMID 5641719. 
  8. ↑ 8.0 8.1 "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry 22 (4): 428–32. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  9. ↑ "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. 
  10. ↑ "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci 15 (24): 4458–4477. December 2024. doi:10.1021/acschemneuro.4c00513. PMID 39636099. 
  11. ↑ "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA". New drugs in Europe, 2012. https://www.emcdda.europa.eu/system/files/publications/734/EMCDDA-Europol_2012_Annual_Report_final_439477.pdf. 
  12. ↑ "Forskrift om endring i forskrift om narkotika" (in Norwegian). Lovdata. https://lovdata.no/dokument/LTI/forskrift/2013-12-16-1557. 
  13. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  14. ↑ "5-MeO-MET" (in ru). https://aipsin.com/newsubstance/135/. 
  15. ↑ 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 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:5-MeO-MET&oldid=4243343"