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

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.

Column 1

DOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
Oral
Serotonergic psychedelic; Hallucinogen
.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None
1–2 hoursPeak: 3 hours
12–16 hours
IUPAC name
1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine
121649-01-2 Y
14201982
21106293 Y
72UT55MXE3
ChEMBL123685 Y
DTXSID00557322
C13H20FNO2
241.306 g·mol−1
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 YKey:QLENKWFQUHHBKZ-UHFFFAOYSA-N Y
.mw-parser-output .nobold{font-weight:normal} NY (what is this?) (verify)

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.

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. The drug's onset was 1 to 2 hours and peak effects occurred after 3 hours. 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.

The chemical synthesis of DOEF has been described.

Analogues of DOEF include 2C-EF, DOET, DOTFE, DOPF, and DOTFM, among others.

DOEF was first described in the scientific literature by Alexander Shulgin and colleagues in 1988. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

DOEF is a controlled substance in Canada under phenethylamine blanket-ban language.

DOx (psychedelics)
DOEF - Isomer Design
DOEF - PiHKAL - Erowid
DOEF - PiHKAL - Isomer Design
The Small & Handy DOEF Thread - Bluelight
DOEF: Here's What Little We Know - Tripsitter

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