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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
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H15FN2
Molar mass206.264g·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,5-6H2,1-2H3checkY
  • Key:BXYDWQABVPBLBU-UHFFFAOYSA-NcheckY
☒NcheckY(what is this?)(verify)

5-Fluoro-N,N-dimethyltryptamine(5-fluoro-DMT,5F-DMT) is atryptaminederivative related to compounds such as5-bromo-DMTand5-MeO-DMT.[1]Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/Creceptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2Aagonist (cf.lisuride), while4-fluoro-5-methoxy-DMTis a much stronger agonist at 5-HT1Athan 5-HT2A.[2][3]

See also

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References

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  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.PMID11101361.
  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.PMID11900766.S2CID6480715.