3C-DFE

3C-DFE is a lesser-known psychedelic drug, which is a fluorinated derivative of 3C-E. It was first synthesised by Daniel Trachsel in 2002,[1][2] and has been reported as showing similar psychedelic activity to related compounds, with a dose range of around 20–40 mg and a duration of approximately 10 hours.[3]: 736  Despite its reported psychedelic activity, binding studies in vitro showed 3C-DFE to have a surprisingly weak binding affinity of 2695 nM at 5-HT2A with negligible affinity at 5-HT2C,[3]: 737  making it only slightly higher affinity than mescaline, despite its higher potency in vivo.

3C-DFE
Names
Preferred IUPAC name
1-[4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenyl]propan-2-amine
Other names
3C-DFE
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • 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
  • InChI=1/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-UHFFFAOYAC
SMILES
  • COc1cc(CC(N)C)cc(OC)c1OCC(F)F
Properties
Chemical formula
 C13H19FNO3
Molar mass 275.292 g/mol
Melting point 171–172 °C (340–342 °F; 444–445 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. 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.
  2. Trachsel, Daniel (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–90. doi:10.1002/dta.413. PMID 22374819.
  3. Daniel Trachsel, David Lehmann and Christoph Enzensperger (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.


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