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5-Fluoro-DMT

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5-Fluoro-DMT
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
FormulaC12H15FN2
Molar mass206.264 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 checkY
  • Key:BXYDWQABVPBLBU-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Fluoro-N,N-dimethyltryptamine (5-fluoro-DMT, 5F-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT.[1]

It is known to have affinity for and to act as an agonist of the serotonin 5-HT1A and 5-HT2A receptors.[2][3] Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C 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 5-HT1A than 5-HT2A.[4][5]

5F-DMT produces a robust head-twitch response in mice, and hence is a putative serotonergic psychedelic.[6] In another study however, it failed to substitute for LSD in rodent drug discrimination tests, at least at the assessed doses.[7]

See also

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References

[edit]
  1. ^ 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.
  2. ^ 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.
  3. ^ 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
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ Blair JB (August 1997). "Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine". Purdue e-Pubs. Retrieved 20 March 2025.


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