5-Fluoro-DMT

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] 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.[2][3]

5-Fluoro-DMT
Identifiers
  • 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
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)

See also

References
  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. Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE (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.
  3. 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.
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