{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = DOTFE.svg | image_class = skin-invert-image | width = 250px | caption =

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<!-- Identifiers --> | CAS_number = | CAS_supplemental = | PubChem = 170143488 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 4-(2,2,2-Trifluoroethyl)-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine

<!-- Chemical data --> | IUPAC_name = 1-[2,5-dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]propan-2-amine | C=13 | H=18 | F=3 | N=1 | O=2 | SMILES = COc1cc(CC(F)(F)F)c(cc1CC(N)C)OC | StdInChI = 1S/C13H18F3NO2/c1-8(17)4-9-5-12(19-3)10(6-11(9)18-2)7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3 | StdInChIKey = OZFGHDLWUVVAPY-UHFFFAOYSA-N }}

'''DOTFE''', also known as '''4-(2,2,2-trifluoroethyl)-2,5-dimethoxyamphetamine''', is a drug of the phenethylamine, amphetamine, and DOx families.<ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | pages = 769, 778–780 | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de | quote = Das Fluoranalogon DOEF (77, 2–3.5mg, 12–16h) ist im Menschen rund doppelt so potent wie DOET (14, 2–6mg, 14–20h) und wirkt nur Unwesentlich kürzer [8]. Von DOEF (77), DOPF (78) und DOPF-2 (79) wurden zumindest die Affinitäten zu den 5-HT2-Rezeptoren bestimmt [54] (siehe Tabelle 2). Das Trifluoroethylderivat DOTFE (51) wurde von Trachsel et al. hergestellt (Synthese siehe Abb. 8) [37]. Seine Wirkung im Menschen ist bis anhin unbekannt (0.56mg und 3mg erwiesen sich als wirkungslos); es dürfte sich um eine potente Substanz handeln. Das Fluormethyl- oder Difiuormethyklerivat 80 [(DOFM)] und 81 [(DODFM)] wären weitere mögliche 5-HT2-Liganden. }}</ref><ref name="Schulze-Alexandru_1999">{{cite journal | vauthors = Schulze-Alexandru M, Kovar KA, Vedani A | title = Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances | journal = Quantitative Structure-Activity Relationships | volume = 18 | issue = 6 | pages = 548–560 | date = 1999 | doi = 10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B | issn = 0931-8771 | doi-access = free | url = http://www.erowid.org/archive/rhodium/pdf/quasi-atomistic.sar.pea.pdf | access-date = 15 July 2025 }}</ref><ref name="Trachsel_2012">{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | date = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | quote = In humans, 2C-TFE (56) proved to be a potent (5–15 mg) and long-lasting (12–24 h) psychedelic. The homolog DOTFE (57) turned out to be without effects in a single 0.56 mg trial. One might expect this to be a potent 5-HT2A receptor agonist with a potential for high human potency but further studies are needed. }}</ref> It is a close analogue of known psychedelics like the DOx psychedelic DOTFM and the 2C psychedelics 2C-TFE and 2C-TFM.<ref name="Trachsel_2013" /><ref name="Trachsel_2012" /><ref name="Schulze-Alexandru_1999" /> The drug was predicted to bind to the serotonin 5-HT<sub>2A</sub> receptor, with a predicted affinity (K<sub>i</sub>) of 50{{nbsp}}nM.<ref name="Schulze-Alexandru_1999" /> It was inactive in humans at doses of up to 3{{nbsp}}mg, but higher doses were not assessed.<ref name="Trachsel_2013" /><ref name="Trachsel_2012" /> DOTFE is expected to be a potent psychedelic at active doses.<ref name="Trachsel_2013" /> It was first described in the scientific literature by at least 1999.<ref name="Schulze-Alexandru_1999" /> DOTFE was evaluated in humans by Daniel Trachsel, with these reports published in 2012 and 2013.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" />

==See also== * DOx (psychedelics)

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/473 DOTFE - Isomer Design]

{{Phenethylamines}}

Category:Daniel Trachsel Category:DOx (psychedelics) Category:Trifluoroethyl compounds

{{Hallucinogen-stub}}