6-Fluoro-DET

{{Short description|Chemical compound}}

{{infobox drug

| drug_name = 6-Fluoro-DET

| image = 6-Fluoro-DET.svg

| legal_UK =

| legal_DE =

| C = 14 | H = 19 | F = 1 | N = 2

| IUPAC_name = N,N-diethyl-2-(6-fluoro-1H-indol-3-yl)ethanamine

| CAS_number = 2836-69-3

| CAS_number_Ref = {{cascite|correct|CAS}}

| ChEMBL = 444612

| ChemSpiderID = 16436

| PubChem = 17371

| UNII = 0ZD2XR6YPV

| synonyms = {{Unbulleted list

| 6-F-DET

| 6-Fluoro-N,N-diethyltryptamine

| 1H-Indole-3-ethanamine, N,N-diethyl-6-fluoro-

}}

| smiles = CCN(CC)CCC1=CNC2=C1C=CC(=C2)F

| StdInChI = 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

| StdInChIKey = 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. Relatedly, 6-F-DET does not substituted for LSD in drug discrimination tests and does not produce the head-twitch response in rodents.{{cite web | title=Psychedelic-Inspired Medium-Throughput Assays for the Development of Next-Generation Neurotherapeutics | website=ProQuest | url=https://www.proquest.com/openview/556de98980d27bfee6bd3cdef6d94fe0/ | quote=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.}}{{cite web | title=Fluorinated tryptamine compounds, analogues thereof, and methods using same | website=Google Patents | date=2 June 2022 | url=https://patents.google.com/patent/WO2022256554A1/ | access-date=8 April 2025}} For the preceding reasons, it saw some use as an active placebo in early clinical trials of psychedelic drugs but was regarded as having little use otherwise,{{cite journal | vauthors = Faillace LA, Vourlekis A, Szara S | title = Clinical evaluation of some hallucinogenic tryptamine derivatives | journal = The Journal of Nervous and Mental Disease | volume = 145 | issue = 4 | pages = 306–313 | date = October 1967 | pmid = 6076017 | doi = 10.1097/00005053-196710000-00005 | s2cid = 19328310 }} 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.{{cite book | vauthors = Martin WR, Sloan JW | chapter = Pharmacology and Classification of LSD-like Hallucinogens | date = 1977 | veditors = Martin WR | title = Drug Addiction II. Handbuch der experimentellen Pharmakologie |series=Handbook of Experimental Pharmacology | volume = 45 | issue = 2 | pages = 305–368 | publisher = Springer | location = Berlin, Heidelberg | doi = 10.1007/978-3-642-66709-1_3| isbn = 978-3-642-66711-4 }}{{cite journal | vauthors = Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE | title = Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 24 | pages = 4701–4710 | date = November 2000 | pmid = 11101361 | doi = 10.1021/jm000339w }}{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/s0091-3057(01)00720-1 | s2cid = 6480715 }}{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | series = Current Topics in Behavioral Neurosciences| volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 }}{{cite journal | vauthors = Cameron 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 | display-authors = 6 | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C }}{{cite journal | vauthors = Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, Azinfar A, Oh WC, Wetsel WC, Olson DE, Tian L | display-authors = 6 | title = Psychedelic-inspired drug discovery using an engineered biosensor | journal = Cell | volume = 184 | issue = 10 | pages = 2779–2792.e18 | date = May 2021 | pmid = 33915107 | pmc = 8122087 | doi = 10.1016/j.cell.2021.03.043 }}