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6-Fluoro-DET

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
6-Fluoro-DET
Clinical data
Other names6-F-DET; 6-F-DET; 6-Fluoro-N,N-diethyltryptamine
Drug classSerotonin receptor modulator;Serotonin 5-HT2A receptor agonist
Identifiers
  • N,N-diethyl-2-(6-fluoro-1H-indol-3-yl)ethanamine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC14H19FN2
Molar mass234.318 g·mol−1
3D model (JSmol)
  • CCN(CC)CCC1=CNC2=C1C=CC(=C2)F
  • 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, or6-F-DET, also known as6-fluoro-N,N-diethyltryptamine, is asubstituted tryptamine derivative related topsychedelic drugs such asdiethyltryptamine (DET).[1]

Use and effects

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6-Fluoro-DET produces physiological effects but does not producehallucinogenic effects in humans.[1]

Pharmacology

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Pharmacodynamics

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6-Fluoro-DET acts as apartial agonist at theserotonin5-HT2A receptor,[2] but while it produces similar physiological effects topsychedelics, it does not appear to produce psychedelic effects itself even at high doses. Relatedly, 6-F-DET does not substitute forLSD indrug discrimination tests and does not produce thehead-twitch response in rodents.[2][3][4] For the preceding reasons, it saw some use as anactive placebo in earlyclinical trials of psychedelic drugs, but was regarded as having little use otherwise,[5] though more recent research into compounds such asAL-34662,tabernanthalog, andzalsupindole has shown that these kind of non-psychedelic serotonin 5-HT2A agonists can have various useful applications.[6][7][8][9][10][11]

A hypothesis for the lack ofhead-twitch response in mice andhallucinogenic effects in humans is that 6-F-DET acts as a5-HT2A receptor partialagonist of the Gq signaling pathway.[2] This hypothesis explains the lack of hallucinogenic effects of other5-HT2A receptor ligands, which are also weak Gq agonists and below theefficacy threshold found to induce psychedelic effects, like25N-N1-Nap,2-Br-LSD,lisuride,tabernanthalog, and6-MeO-DMT.[2][10][12]

Chemistry

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Analogues

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Analogues of 6-fluoro-DET include6-fluoro-DMT,5-fluoro-DMT,5-chloro-DMT,5-bromo-DMT,5-fluoro-AMT,6-fluoro-AMT,6-methyl-DMT,6-MeO-DMT,6-hydroxy-DMT, andbretisilocin (5-fluoro-MET), among others.

History

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6-Fluoro-DET was first described in thescientific literature byStephen Szara and colleagues by 1963.[13]

See also

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References

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  1. ^abShulgin, Alexander;Shulgin, Ann (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
  2. ^abcdWallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar RJ, Halberstadt AL, McCorvy JD (2023)."Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential".Nature Communications.14 (1): 8221.doi:10.1038/s41467-023-43904-4.PMC 10694965.PMID 38001451.
  3. ^"Psychedelic-Inspired Medium-Throughput Assays for the Development of Next-Generation Neurotherapeutics".ProQuest.6-F-DMT has been thought to be non-hallucinogenic as 6-F-DET (6-fluoro-N,N-diethyltryptamine) has been shown to not substitute for LSD in DD.
  4. ^"Fluorinated tryptamine compounds, analogues thereof, and methods using same".Google Patents. 2 June 2022. Retrieved8 April 2025.
  5. ^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.
  6. ^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.
  7. ^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.
  8. ^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.
  9. ^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.
  10. ^abCameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE (2021)."A non-hallucinogenic psychedelic analogue with therapeutic potential".Nature.589 (7842):474–479.doi:10.1038/s41586-020-3008-z.PMC 7874389.PMID 33299186.
  11. ^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.
  12. ^Glatfelter GC, Pottie E, Partilla JS, Stove CP, Baumann MH (2024). "Comparative pharmacological effects of lisuride and lysergic acid diethylamide revisited".ACS Pharmacology & Translational Science.7 (3):641–653.doi:10.1021/acsptsci.3c00274.
  13. ^Kalir A, Szara S (November 1963). "Synthesis and pharmacological activity of fluorinated tryptamine derivatives".J Med Chem.6:716–719.doi:10.1021/jm00342a019.PMID 14184932.

External links

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