3C-DFE

{{Short description|Psychedelic drug}}

{{chembox

| ImageFile = 3C-DFE_structure.png

| PIN = 1-[4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenyl]propan-2-amine

| OtherNames = 3C-DFE

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 33260397

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 501700-07-8

| PubChem = 54939285

| SMILES = COc1cc(CC(N)C)cc(OC)c1OCC(F)F

| 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

| InChIKey = TYXHBMNQOVLYRX-UHFFFAOYAC

| StdInChI = 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

| StdInChIKey = TYXHBMNQOVLYRX-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula =

| C=13 | H=19 | F=1 | N=1 | O=3

| MolarMass = 275.292 g/mol

| Appearance =

| Density =

| MeltingPtC = 171-172

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

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,{{cite journal | doi = 10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4| year = 2002| last1 = Trachsel| first1 = Daniel| journal = Helvetica Chimica Acta| volume = 85| issue = 9| pages = 3019–3026 | title = Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate}}{{cite journal | doi = 10.1002/dta.413| pmid = 22374819| title = Fluorine in psychedelic phenethylamines| journal = Drug Testing and Analysis| volume = 4| issue = 7–8| pages = 577–90| year = 2012| last1 = Trachsel| first1 = Daniel}} 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.{{Cite book | author = Daniel Trachsel, David Lehmann and Christoph Enzensperger | title = Phenethylamine Von der Struktur zur Funktion | publisher = Nachtschatten Verlag AG | date = 2013 | isbn = 978-3-03788-700-4}}{{rp|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,{{rp|737}} making it only slightly higher affinity than mescaline, despite its higher potency in vivo.