# DOTFE

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/DOTFE
> Markdown URL: https://mediated.wiki/source/DOTFE.md
> Source: https://en.wikipedia.org/wiki/DOTFE
> Source revision: 1338612500
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

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| image = DOTFE.svg
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| 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](/source/drug) of the [phenethylamine](/source/substituted_phenethylamine), [amphetamine](/source/substituted_amphetamine), and [DOx](/source/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](/source/structural_analog) of known [psychedelic](/source/psychedelic_drug)s like the DOx psychedelic [DOTFM](/source/DOTFM) and the [2C](/source/2C_(psychedelics)) psychedelics [2C-TFE](/source/2C-TFE) and [2C-TFM](/source/2C-TFM).<ref name="Trachsel_2013" /><ref name="Trachsel_2012" /><ref name="Schulze-Alexandru_1999" /> The drug was predicted to bind to the [serotonin](/source/serotonin) [5-HT<sub>2A</sub> receptor](/source/5-HT2A_receptor), with a predicted [affinity](/source/affinity_(pharmacology)) (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](/source/potency_(pharmacology)) psychedelic at active doses.<ref name="Trachsel_2013" /> It was first described in the [scientific literature](/source/scientific_literature) by at least 1999.<ref name="Schulze-Alexandru_1999" /> DOTFE was evaluated in humans by [Daniel Trachsel](/source/Daniel_Trachsel), with these reports published in 2012 and 2013.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" />

==See also==
* [DOx (psychedelics)](/source/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}}

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Adapted from the Wikipedia article [DOTFE](https://en.wikipedia.org/wiki/DOTFE) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/DOTFE?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.