6-Fluoro-DET

6-Fluoro-DET

Clinical data
Other names	6-F-DET 6-Fluoro-N,N-diethyltryptamine 1H-Indole-3-ethanamine, N,N-diethyl-6-fluoro-
Identifiers
IUPAC name N,N-diethyl-2-(6-fluoro-1H-indol-3-yl)ethanamine
CAS Number	2836-69-3  Y
PubChem CID	17371
ChemSpider	16436
UNII	0ZD2XR6YPV
ChEMBL	ChEMBL444612
CompTox Dashboard (EPA)	DTXSID301345652
Chemical and physical data
Formula	C14H19FN2
Molar mass	234.318 g·mol−1
3D model (JSmol)	Interactive image
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-HT_2A 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, ^[1] though more recent research into compounds such as AL-34662, TBG and zalsupindole has shown that these kind of non-psychedelic 5-HT_2A agonists can have various useful applications. ^{[2] [3] [4] [5] [6] [7]}

See also

• 5F-DMT
• 5F-DET
• 5F-MET
• 5F-EPT
• 6F-AMT
• 6F-DMT
• 6-MeO-DMT
• 6-MeO-isoDMT

References

1. Faillace LA, Vourlekis A, Szara S (October 1967). "Clinical evaluation of some hallucinogenic tryptamine derivatives". The Journal of Nervous and Mental Disease. 145 (4): 306–313. doi:10.1097/00005053-196710000-00005. PMID   6076017. S2CID   19328310.
2. 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. Vol. 45. Berlin, Heidelberg: Springer. pp. 305–368. doi:10.1007/978-3-642-66709-1_3. ISBN   978-3-642-66711-4.
3. 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.
4. 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.
5. Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524.
6. Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, et al. (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. PMC   7874389 . PMID   33299186.
7. Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021). "Psychedelic-inspired drug discovery using an engineered biosensor". Cell. 184 (10): 2779–2792.e18. doi:10.1016/j.cell.2021.03.043. PMC   8122087 . PMID   33915107.