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5-MeO-MET

Topic: Chemistry

 From HandWiki - Reading time: 15 min

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] However, Nervewing later described the effects of 5-MeO-MET in an interview with Hamilton Morris and elsewhere.[7] They described 5-MeO-MET as producing no interesting psychological effects, as feeling like they had purely physically poisoned themselves, as feeling terrible and miserable, and as causing specific symptoms including nausea, chills, muscle aches, and almost vomiting, among others.[7]

Interactions

Pharmacology

Pharmacodynamics

Early studies found 5-MeO-MET to be more potent in animal behavioral tests than 5-MeO-DMT.[2][8] Subsequent studies confirmed that 5-MeO-MET interacts with serotonin receptors similarly to other psychedelic tryptamines.[9][10] 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][11] 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][8][9] The drug was first identified on the illicit market in June 2012 in Sweden.[12] It was made illegal in Norway in 2013.[13]

Society and culture

Canada

5-MeO-MET is not a controlled substance in Canada as of 2025.[14]

Sweden

5-MeO-MET is a controlled substance in Sweden.[15]

United States

5-MeO-MET is not an explicitly controlled substance in the United States.[16] 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 Hamilton Morris (12 May 2026). "POD 144: Nervewing on the Joy and Danger of Exploring New Chemical Frontiers". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:03:57–10:04:25. [...] [Nervewing:] There were some things I took that just like I felt like I'd physically poisoned myself. Uh, 5-MeO-MET, that compound felt terrible to me. I literally like didn't get any even interesting psychological effects. It was purely just like I felt like I physically poisoned myself. Um, just nausea, chills, muscle aches, um, like almost like throwing up, it was just miserable. [...] [Nervewing:] I wrote a report about it. [...]
  8. ↑ 8.0 8.1 "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. 
  9. ↑ 9.0 9.1 "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry 22 (4): 428–32. April 1979. doi:10.1021/jm00190a014. PMID 430481. 
  10. ↑ "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. 
  11. ↑ "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. 
  12. ↑ "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. 
  13. ↑ "Forskrift om endring i forskrift om narkotika" (in Norwegian). Lovdata. https://lovdata.no/dokument/LTI/forskrift/2013-12-16-1557. 
  14. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  15. ↑ "5-MeO-MET" (in ru). https://aipsin.com/newsubstance/135/. 
  16. ↑ 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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