Chemistry:5-Fluoro-DMT

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5-Fluoro-DMT, or 5-F-DMT, also known as 5-fluoro-N,N-dimethyltryptamine, is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and to other psychedelic tryptamines like 5-chloro-DMT and 5-bromo-DMT.[1][2]

Use and effects

5-Fluoro-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[3]

Interactions

Pharmacology

Pharmacodynamics

5-Fluoro-DMT is known to have affinity for and to act as an agonist of the serotonin 5-HT1A and 5-HT2A receptors.[1][4][5] Fluorination of psychedelic tryptamines either reduces or has little effect on serotonin 5-HT2A and 5-HT2C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist (cf. lisuride), while 4-fluoro-5-methoxy-DMT is a much stronger agonist at the serotonin 5-HT1A receptor than at the serotonin 5-HT2A receptor.[6][7]

5-Fluoro-DMT produces a robust head-twitch response in mice, and hence is a putative serotonergic psychedelic.[8][1][9] In another study however, it failed to substitute for LSD in rodent drug discrimination tests, at least at the assessed doses.[10] The drug also produces hypolocomotion and hypothermia in rodents.[1]

Chemistry

Analogues

Analogues of 5-fluoro-DMT include dimethyltryptamine (DMT), 5-fluorotryptamine (5-fluoro-T), 5-bromo-DMT, 5-chloro-DMT, bretisilocin (5-fluoro-MET), 5-fluoro-DET, 4-fluoro-DMT, 6-fluoro-DMT, 6-fluoro-DET, 4-fluoro-5-methoxy-DMT, 5-fluoro-AMT, 6-fluoro-AMT, and O-4310 (1-iPr-6-F-4-HO-DMT), among others.

History

5-Fluoro-DMT was first described in the scientific literature by Stephen Szára and colleagues by 1966.[11]

Society and culture

Canada

5-Fluoro-DMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.[12]

United States

5-Fluoro-DMT is not an explicitly controlled substance in the United States.[13] 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 "Neuropharmacology of halogenated DMT analogs: psychoplastogenic and antidepressant properties of 5-Br-DMT, a psychedelic derivative with low hallucinogenic potential". Mol Psychiatry. October 2025. doi:10.1038/s41380-025-03308-2. PMID 41120735. 
  2. ↑ "Improved Fischer indole reaction for the preparation of N, N-dimethyltryptamines: Synthesis of L-695,894, a potent 5-HT1D receptor agonist.". The Journal of Organic Chemistry 59 (13): 3738–3741. July 1994. doi:10.1021/jo00092a046. 
  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. 
  4. ↑ "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem 299 (10). October 2023. doi:10.1016/j.jbc.2023.105231. PMID 37690691. 
  5. ↑ Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery, 10 March 2023, doi:10.21203/rs.3.rs-2667175/v1, https://www.researchsquare.com/article/rs-2667175/latest.pdf, retrieved 18 March 2025 
  6. ↑ "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry 43 (24): 4701–10. November 2000. doi:10.1021/jm000339w. PMID 11101361. 
  7. ↑ "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior 72 (1–2): 29–37. May 2002. doi:10.1016/S0091-3057(01)00720-1. PMID 11900766. 
  8. ↑ "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. 
  9. ↑ "5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice". Neuroscience Applied 3. 2024. doi:10.1016/j.nsa.2024.104390. 
  10. ↑ Blair JB (August 1997). Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine (Ph.D. thesis). Purdue University. Retrieved 20 March 2025 – via Purdue e-Pubs.
  11. ↑ "Synthesis and pharmacological activity of alkylated tryptamines". J Med Chem 9 (3): 341–344. May 1966. doi:10.1021/jm00321a017. PMID 5960901. 
  12. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  13. ↑ 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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