2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug pf the phenethylamine, amphetamine, and DOx families.^[1][2][3] In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOEF's dose as 2 to 3.5 mg orally and its duration as 12 to 16 hours.^[1] The drug's onset was 1 to 2 hours and peak effects occurred after 3 hours.^[1] The effects of DOEF were reported to include unworldliness, closed-eye imagery no appreciable open-eye visuals or not highly visual, time dilation, music and erotic enhancement, no body discomfort, insomnia, and sleep disruption, among others.^[1] DOEF was first described in the scientific literature by Alexander Shulgin and colleagues in 1988.^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]

DOEF

Clinical data
Other names	DOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Onset of action	1–2 hours[1] Peak: 3 hours[1]
Duration of action	12–16 hours[1]
Identifiers
IUPAC name 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine
CAS Number	121649-01-2 Y
PubChem CID	14201982
ChemSpider	21106293 Y
UNII	72UT55MXE3
ChEMBL	ChEMBL123685 Y
CompTox Dashboard (EPA)	DTXSID00557322
Chemical and physical data
Formula	C13H20FNO2
Molar mass	241.306 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC
InChI InChI=1S/C13H20FNO2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4-6,15H2,1-3H3 Y Key:QLENKWFQUHHBKZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

See also

• DOx (psychedelics)
• DOET
• DOPF
• DOTFM