Article · Wikipedia archive · Last revised Jun 7, 2026

DOTFE

DOTFE, also known as 4-(2,2,2-trifluoroethyl)-2,5-dimethoxyamphetamine, is a drug of the phenethylamine, amphetamine, and DOx families. It is a close analogue of known psychedelics like the DOx psychedelic DOTFM and the 2C psychedelics 2C-TFE and 2C-TFM. The drug was predicted to bind to the serotonin 5-HT2A receptor, with a predicted affinity (Ki) of 50 nM. It was inactive in humans at doses of up to 3 mg, but higher doses were not assessed. DOTFE is expected to be a potent psychedelic at active doses. It was first described in the scientific literature by at least 1999. DOTFE was evaluated in humans by Daniel Trachsel, with these reports published in 2012 and 2013.

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Jun 7, 2026
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DOTFE
Clinical data
Other names4-(2,2,2-Trifluoroethyl)-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine
ATC code
  • None
Identifiers
  • 1-[2,5-dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]propan-2-amine
PubChem CID
Chemical and physical data
FormulaC13H18F3NO2
Molar mass277.287 g·mol−1
3D model (JSmol)
  • COc1cc(CC(F)(F)F)c(cc1CC(N)C)OC
  • InChI=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
  • Key: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.123 It is a close analogue of known psychedelics like the DOx psychedelic DOTFM and the 2C psychedelics 2C-TFE and 2C-TFM.132 The drug was predicted to bind to the serotonin 5-HT2A receptor, with a predicted affinity (Ki) of 50 nM.2 It was inactive in humans at doses of up to 3 mg, but higher doses were not assessed.13 DOTFE is expected to be a potent psychedelic at active doses.1 It was first described in the scientific literature by at least 1999.2 DOTFE was evaluated in humans by Daniel Trachsel, with these reports published in 2012 and 2013.31

See also

See also

References

References

  1. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 769, 778–780. ISBN 978-3-03788-700-4. OCLC 858805226. 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.
  2. Schulze-Alexandru M, Kovar KA, Vedani A (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances" (PDF). Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. Retrieved 15 July 2025.
  3. Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819. 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.
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