DOTFE

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
CAS Number
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.[1][2][3] It is a close analogue of known psychedelics like the DOx psychedelic DOTFM and the 2C psychedelics 2C-TFE and 2C-TFM.[1][3][2] 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.[1][3] 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.[3][1]

See also

References

  1. ^ a b c d e 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. ^ a b c d 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. ^ a b c d 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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