6-Fluoro-DET

6-Fluoro-DET
Identifiers
IUPAC name
  • N,N-diethyl-2-(6-fluoro-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H19FN2
Molar mass234.318 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)CCC1=CNC2=C1C=CC(=C2)F
InChI
  • InChI=1S/C14H19FN2/c1-3-17(4-2)8-7-11-10-16-14-9-12(15)5-6-13(11)14/h5-6,9-10,16H,3-4,7-8H2,1-2H3
  • Key:RPWUTEXLVPDNEA-UHFFFAOYSA-N

6-Fluoro-DET (6F-DET, 6-fluoro-N,N-diethyltryptamine) is a substituted tryptamine derivative related to drugs such as DET and 5-fluoro-DET. It acts as a partial agonist at the 5-HT2A receptor, but while it produces similar physiological effects to psychedelic drugs, it does not appear to produce psychedelic effects itself even at high doses. For this reason it saw some use as an active placebo in early clinical trials of psychedelic drugs but was regarded as having little use otherwise, though more recent research into compounds such as AL-34662 and AAZ-A-154 has shown that these kind of non-psychedelic 5-HT2A agonists can have various useful applications.[1][2][3][4]

See also

References

  1. ↑ Martin WR, Sloan JW (1977). "Pharmacology and Classification of LSD-like Hallucinogens.". In Martin WR (ed.). Drug Addiction II. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology (Heffter-Heubner / New Series). Vol. 45. Berlin, Heidelberg: Springer. pp. 305–368. doi:10.1007/978-3-642-66709-1_3. ISBN 978-3-642-66711-4.
  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): 4701–4710. 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.
  4. ↑ Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
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