{{Short description|Chemical compound}} {{Infobox drug | image = 6-fluoro-AMT.svg | image_class = skin-invert-image | width = 225px | image2 = 6-Fluoro-AMT 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | routes_of_administration = Oral | class = Serotonergic psychedelic; Hallucinogen
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 712-11-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 46F5HN29NW | PubChem = 15289992 | ChemSpiderID = 14228507 | synonyms = 6-Fluoro-AMT; 6-Fluoro-αMT; 6F-AMT; 6F-αMT; 6-F-AMT; 6-F-αMT; 6-Fluoro-α-methyltryptamine
<!-- Chemical data --> | IUPAC_name = 1-(6-fluoro-1''H''-indol-3-yl)propan-2-amine | C=11 | H=13 | F=1 | N=2 | SMILES = NC(C)CC1=CNC2=CC(F)=CC=C21 | StdInChI = 1S/C11H13FN2/c1-7(13)4-8-6-14-11-5-9(12)2-3-10(8)11/h2-3,5-7,14H,4,13H2,1H3 | StdInChIKey = XYJYWUUXCUJXAI-UHFFFAOYSA-N }}
'''6-Fluoro-AMT''', or '''6-fluoro-αMT''', also known as '''6-fluoro-α-methyltryptamine''', is a psychedelic drug of the tryptamine family related to α-methyltryptamine (AMT) and 5-MeO-AMT.<ref name="Morris2010" /><ref name="ThisLandPress2013" />
==Use and effects== 6-Fluoro-AMT was allegedly manufactured and sold from the laboratory operated by Leonard Pickard and Gordon Todd Skinner, who described 6-fluoro-AMT as "a beast".<ref name="Morris2010">{{Cite web |url=https://www.vice.com/en/article/getting-high-on-krystle-trailer/ |title=Life is a Cosmic Giggle on the Breath of the Universe. A Tour of Gordon Todd Skinner's Subterranean LSD Palace. | first = Hamilton | last = Morris | name-list-style = vanc | work = Vice Magazine | date = 2010 |access-date=2017-08-23 |archive-url=https://web.archive.org/web/20141013173933/http://www.vice.com/hamiltons-pharmacopeia/getting-high-on-krystle-trailer |archive-date=2014-10-13 |url-status=live }}</ref> In interviews, Skinner stated that he first began to experiment with 6-fluoro-AMT in the early 1980s by giving it to high school friends.<ref name="ThisLandPress2013" /> Their experiences made him cautious about the appropriate doses, which he said ranged from 25 to 75{{nbsp}}mg (Skinner weighed about 250{{nbsp}}lbs at the time of his own bioassay).<ref name="ThisLandPress2013" /> Skinner said that 6-fluoro-AMT is a long-lasting psychedelic with more time distortion and that it was enhanced by combination with ALD-52.<ref name="ThisLandPress2013">{{cite web |title= Unusual Analogues: Drugs Used by Gordon Todd Skinner |url= http://thislandpress.com/2013/07/25/unusual-analogues-drugs-used-by-gordon-todd-skinner/ | archive-url=https://web.archive.org/web/20160417235026/http://thislandpress.com/2013/07/25/unusual-analogues-drugs-used-by-gordon-todd-skinner/ | archive-date =17 April 2016 | website= thislandpress.com |publisher=This Land Press |access-date=8 April 2016}}</ref>
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== Animal tests showed the drug to be somewhat less potent in terms of pharmacological activity than AMT or 5-fluoro-AMT.<ref name="KalirSzara1963">{{cite journal | vauthors = Kalir A, Szara S | journal = Journal of Medicinal Chemistry | volume = 6 | issue = 6 | pages = 716–719 | date = November 1963 | pmid = 14184932| doi = 10.1021/jm00342a019 | title = Synthesis and Pharmacological Activity of Fluorinated Tryptamine Derivatives }}</ref> It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.<ref name="HalberstadtGeyer2018">{{cite book | vauthors = Halberstadt AL, Geyer MA | title = Behavioral Neurobiology of Psychedelic Drugs | chapter = Effect of Hallucinogens on Unconditioned Behavior | series = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | isbn = 978-3-662-55878-2 | chapter-url = }}</ref><ref name="NakagawasaiAraiSatoh2004">{{cite journal | vauthors = Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T | title = Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives | journal = Neurotoxicology | volume = 25 | issue = 1–2 | pages = 223–232 | date = January 2004 | pmid = 14697897 | doi = 10.1016/S0161-813X(03)00101-3 | bibcode = 2004NeuTx..25..223N | url = }}</ref><ref name="TadanoNedaHozumi1995">{{cite journal | vauthors = Tadano T, Neda M, Hozumi M, Yonezawa A, Arai Y, Fujita T, Kinemuchi H, Kisara K | title = alpha-Methylated tryptamine derivatives induce a 5-HT receptor-mediated head-twitch response in mice | journal = Neuropharmacology | volume = 34 | issue = 2 | pages = 229–234 | date = February 1995 | pmid = 7617148 | doi = 10.1016/0028-3908(94)00119-d | url = }}</ref> Its {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} for monoamine oxidase A (MAO-A) inhibition is 580 to 1,800{{nbsp}}nM, compared to 180 to 450{{nbsp}}nM for 5-fluoro-AMT and 380{{nbsp}}nM for AMT.<ref name="NakagawasaiAraiSatoh2004" /><ref name="WagmannBrandtKavanagh2017">{{cite journal | vauthors = Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR | title = In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | journal = Toxicol Lett | volume = 272 | issue = | pages = 84–93 | date = April 2017 | pmid = 28302559 | doi = 10.1016/j.toxlet.2017.03.007 | url = https://researchonline.ljmu.ac.uk/id/eprint/5909/1/TOXLET-D-17-00086R1_accepted_uncorected.pdf}}</ref><ref name="WO2022061242A1">{{cite patent | country = WO | number = 2022061242 | inventor = Matthew Baggott | status = | title = Advantageous tryptamine compositions for mental disorders or enhancement | pubdate = 2023 March 24 | gdate = | fdate = 2021 September 20 | pridate = 2021 September 20 | assign1 = Tactogen | url = https://patents.google.com/patent/WO2022061242A1/}}</ref>
==Chemistry== ===Analogues=== Analogues of 6-fluoro-AMT include α-methyltryptamine (AMT), 5-fluoro-AMT, 5-chloro-AMT, 5-fluoro-AET, 5-chloro-AET, 6-fluoro-DMT, 6-fluoro-DET, 6-methyl-DMT, 6-MeO-DMT, 6-hydroxy-DMT, 7-chloro-AMT, and O-4310 (1-isopropyl-6-fluoro-4-HO-DMT), among others.
==History== 6-Fluoro-AMT was first described in the scientific literature, by Asher Kalir and Stephen Szara, by at least 1963.<ref name="KalirSzara1963" />
==Society and culture== ===Legal status=== ====Canada==== 6-Fluoro-AMT is not an explicitly nor implicitly controlled substance in Canada as of 2025.<ref name="CDSA2025">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | date=5 December 2025 | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=20 January 2026}}</ref>
====United States==== 6-Fluoro-AMT is not an explicitly controlled substance in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
==See also== * Substituted α-alkyltryptamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5105 6-Fluoro-AMT - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Monoamine metabolism modulators}} {{Tryptamines}}
Category:5-HT2A agonists Category:Alpha-Alkyltryptamines Category:Fluoroarenes Category:Monoamine oxidase inhibitors Category:Psychedelic tryptamines Category:Serotonin receptor agonists