5-Fluoro-DMT

Use and effects

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

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. 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.

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

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.

Society and culture

Legal status

Canada

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

United States

5-Fluoro-DMT is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

References

1. (October 2025). "Neuropharmacology of halogenated DMT analogs: psychoplastogenic and antidepressant properties of 5-Br-DMT, a psychedelic derivative with low hallucinogenic potential". Mol Psychiatry.
2. (July 1994). "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.
3. {{CiteTiHKAL
4. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem.
5. (10 March 2023). "Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery".
6. (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry.
7. (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior.
8. (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev.
9. (2024). "5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice". Neuroscience Applied.
10. (August 1997). "Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine". Purdue University.
11. (May 1966). "Synthesis and pharmacological activity of alkylated tryptamines". J Med Chem.
12. (5 December 2025). "Controlled Drugs and Substances Act".
13. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.