Difluoroescaline

Difluoroescaline
Clinical data
Other namesDFE; 2,2-DFE; F2EM; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(2,2-difluoroethoxy)phenethylamine
Routes of
administration		Oral[1][2][3]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action6–12 hours[1][2][3]
Identifiers
  • 2-[4-(2,2-difluoroethoxy)-3,5-dimethoxyphenyl]ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H17F2NO3
Molar mass261.269 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OCC(F)F)OC)CCN
  • InChI=1S/C12H17F2NO3/c1-16-9-5-8(3-4-15)6-10(17-2)12(9)18-7-11(13)14/h5-6,11H,3-4,7,15H2,1-2H3
  • Key:PCAYHBWBNGPKII-UHFFFAOYSA-N

Difluoroescaline (DFE), also known as 4-(2,2-difluoroethoxy)-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][2][3] It is a difluorinated derivative of escaline.[1][2][3] Its dose range is 40 to 80 mg and its duration is 6 to 12 hours.[1][2][3] The drug's effects include color enhancement, some closed-eye and open-eye visuals, emotional changes, and some physical discomfort.[1] It acts as a low-potency partial agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors and targets.[3][2] The chemical synthesis of difluoroescaline has been described.[4] Difluoroescaline was first described in the scientific literature by Daniel Trachsel in 2002.[1][2][3][4] Its pharmacology was studied in more detail in 2021.[3] It is not a controlled substance in Canada as of 2025.[5]

See also

References

  1. ^ a b c d e f g 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. 706, 710–711, 716–717, 736–737. ISBN 978-3-03788-700-4. OCLC 858805226.
  2. ^ a b c d e f g Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819. Difluoroescaline (77), on the other hand, retained, and trifluoroescaline (78) showed increased human potency of escaline (70). [...] The trifluoroethyl derivative 78 (35–65 mg, 12–18 h) proved to be a psychedelic compound of similar or slightly increased human potency with a prolonged duration of action. [...] Three fluoro analogs (76–78) of escaline (70) have been investigated.[86] At the [3 H]ketanserin-labelled serotonin h5-HT2A receptor both fluoroescaline (76: Ki = 7628nM) and difluoroescaline (77: Ki > 10000nM) showed low affinities. Interestingly, with monofluorination the human potency of 76 (75 mg, ~6 h) decreased distinctly, while the difluoro analog 77 (40–80 mg, 6–12 h) regained similar potency to the non-fluorinated derivative escaline (70: 40–60 mg, 8–12 h). The trifluoroethyl derivative 78 (35–65 mg, 12–18 h) proved to be a psychedelic compound of similar or slightly increased human potency with a prolonged duration of action. [...] With compounds 76–78 it has been shown that fluorination of the 4-ethoxy group of escaline (70) can change the (psycho)pharmacological properties profoundly. While monofluorination causes loss of psychoactivity (compound 76), difluorination retains human potency (compound 77) and the trifluoroethoxy derivative 78 proved to be a long-lasting psychedelic with similar or slightly increased potency.
  3. ^ a b c d e f g h Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Frontiers in Pharmacology. 12 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
  4. ^ a b Trachsel D (2002). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate". Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.