3C-DFE

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Wikipedia

3C-DFE
Clinical data
Other names3C-F2EM; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyamphetamine; α-Methyldifluoroescaline; 3C-Difluoroescaline
Routes of
administration		Oral[1][2]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action~10 hours[1][2]
Identifiers
  • 1-[4-(2,2-difluoroethoxy)-3,5-dimethoxyphenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H19F2NO3
Molar mass275.296 g·mol−1
3D model (JSmol)
Melting point171 to 172 °C (340 to 342 °F)
  • COc1cc(CC(N)C)cc(OC)c1OCC(F)F
  • InChI=1S/C13H19F2NO3/c1-8(16)4-9-5-10(17-2)13(11(6-9)18-3)19-7-12(14)15/h5-6,8,12H,4,7,16H2,1-3H3
  • Key:TYXHBMNQOVLYRX-UHFFFAOYSA-N

3C-DFE, also known as 4-(2,2-difluoroethoxy)-3,5-dimethoxyamphetamine or as α-methyldifluoroescaline (3C-difluoroescaline), is a lesser-known psychedelic drug of the phenethylamine, amphetamine, and 3C families, which is a fluorinated derivative of 3C-E.[1][3][4][2] It was first synthesised by Daniel Trachsel in 2002,[4][3] and has been reported as showing similar psychedelic activity to related compounds, with an active dose of around 22 mg orally and a duration of approximately 10 hours.[1]: 736 

Despite its psychedelic activity, binding studies in vitro showed 3C-DFE to have a surprisingly weak binding affinity of 2,695 nM at the serotonin 5-HT2A receptor with negligible affinity at the serotonin 5-HT2C receptor, making it only slightly higher affinity than mescaline, despite its much higher potency in vivo.[1]: 737  However, the pharmacology of 3C-DFE was subsequently further studied and it was found to be a potent agonist of the seroton 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 120 nM (83-fold that of mescaline in the same study) and an EmaxTooltip maximal efficacy of 95% (relative to 56% with mescaline in the study).[2]

See also

References

  1. 1 2 3 4 5 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 704–723. ISBN 978-3-03788-700-4.
  2. 1 2 3 4 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". Front Pharmacol. 12 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010.
  3. 1 2 Trachsel, Daniel (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–90. doi:10.1002/dta.413. PMID 22374819.
  4. 1 2 Trachsel, Daniel (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.