Trifluoroescaline

Trifluoroescaline
Clinical data
Other namesTFE; 3,3,3-Trifluoroescaline; 3,3,3-TFE; F3EM; 4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)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 action12–18 hours[1][2][3]
Identifiers
  • 2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H16F3NO3
Molar mass279.259 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OCC(F)(F)F)OC)CCN
  • InChI=1S/C12H16F3NO3/c1-17-9-5-8(3-4-16)6-10(18-2)11(9)19-7-12(13,14)15/h5-6H,3-4,7,16H2,1-2H3
  • Key:LMULYKOEWFMASK-UHFFFAOYSA-N

Trifluoroescaline (TFE), also known as 4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1][2][3] It is a trifluorinated derivative of escaline.[1][2][3] The drug has a dose range of 35 to 65 mg orally and a duration of 12 to 18 hours.[1][2][3] It has similar potency to escaline, greatly increased potency relative to mescaline, and a prolonged duration compared to both mescaline and escaline.[1][2][3] The effects of trifluoroescaline have been reported to include enhanced fantasy, strong closed-eye visuals, significant open-eye visuals, and low body load.[1] The drug is a low-potency partial agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors and targets.[3] The chemical synthesis of trifluoroescaline has been described.[4] Trifluoroescaline 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]

See also

References

  1. ^ a b c d e f g h 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, 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. s. 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. [...] 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 i 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.
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