3C-DFE

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

Other names3C-F₂EM; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyamphetamine; α-Methyldifluoroescaline; 3C-Difluoroescaline

Routes of
administrationOral^[1][2]

Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen

ATC code

• None

Quick facts Clinical data, Other names ...

3C-DFE

Clinical data
Other names	3C-F2EM; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyamphetamine; α-Methyldifluoroescaline; 3C-Difluoroescaline
Routes of administration	Oral[1][2]
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	~10 hours[1][2]
Identifiers
IUPAC name 1-[4-(2,2-difluoroethoxy)-3,5-dimethoxyphenyl]propan-2-amine
CAS Number	501700-07-8 Y
PubChem CID	54939285
ChemSpider	33260397 Y
CompTox Dashboard (EPA)	DTXSID701032726
Chemical and physical data
Formula	C13H19F2NO3
Molar mass	275.296 g·mol−1
3D model (JSmol)	Interactive image
Melting point	171 to 172 °C (340 to 342 °F)
SMILES COc1cc(CC(N)C)cc(OC)c1OCC(F)F
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

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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-HT_2A receptor with negligible affinity at the serotonin 5-HT_2C 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 serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 120 nM (83-fold that of mescaline in the same study) and an E_maxTooltip maximal efficacy of 95% (relative to 56% with mescaline in the study).^[2]

It is a controlled substance in Canada under phenethylamine blanket-ban language.^[5]