3C-DFE

3C-DFE
Names
	Preferred IUPAC name 1-[4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenyl]propan-2-amine
	Other names 3C-DFE
Identifiers
CAS Number	501700-07-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	33260397 ;
PubChem CID	54939285;
CompTox Dashboard (EPA)	DTXSID701032726 ;
	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

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-HT_2A with negligible affinity at 5-HT_2C,^[3]^: 737 making it only slightly higher affinity than mescaline, despite its higher potency in vivo.

References

^ 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.
^ Trachsel, Daniel (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–90. doi:10.1002/dta.413. PMID 22374819.
^ ^a ^b 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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[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.

[Trachsel-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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See also

References