5-Fluoro-DMT

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5-Fluoro-DMT
5-Fluoro-DMT structure.png
Clinical data
Other names5-F-DMT; 5F-DMT; 5-Fluoro-N,N-dimethyltryptamine
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H15FN2
Molar mass 206.264 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=C(C=C2)F
  • InChI=1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 Yes check.svgY
  • Key:BXYDWQABVPBLBU-UHFFFAOYSA-N Yes check.svgY
   (verify)

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]

Contents

Use and effects

5-Fluoro-DMT was not included or 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]

See also

References

  1. 1 2 3 4 Puigseslloses P, Nadal-Gratacós N, Fumàs B, Modenutti CP, Pottie E, Ortigosa JR, et al. (October 2025). "Neuropharmacology of halogenated DMT analogs: psychoplastogenic and antidepressant properties of 5-Br-DMT, a psychedelic derivative with low hallucinogenic potential". Mol Psychiatry. doi:10.1038/s41380-025-03308-2. PMID   41120735.
  2. ↑ Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ (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. 59 (13): 3738–3741. doi:10.1021/jo00092a046.
  3. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  4. ↑ Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, et al. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem. 299 (10) 105231. doi: 10.1016/j.jbc.2023.105231 . PMC   10570959 . PMID   37690691.
  5. ↑ Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, et al. (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi: 10.21203/rs.3.rs-2667175/v1 , retrieved 18 March 2025
  6. ↑ Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, et al. (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 43 (24): 4701–10. doi:10.1021/jm000339w. PMID   11101361.
  7. ↑ Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/S0091-3057(01)00720-1. PMID   11900766. S2CID   6480715.
  8. ↑ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123.
  9. ↑ Fumàs B, Nadal-Gratacós N, Pablo-Quesada A, Berzosa X, Camarasa J, Pubill D, et al. (2024). "5-halo-substituted DMT derivatives. Hallucinogenic response and early gene expression in mice". Neuroscience Applied. 3 104390. 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. ↑ Kalir A, Szara S (May 1966). "Synthesis and pharmacological activity of alkylated tryptamines". J Med Chem. 9 (3): 341–344. doi:10.1021/jm00321a017. PMID   5960901.
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