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

DOEF

Clinical data
Other names	DOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
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)

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a lesser-known psychedelic drug and member of the DOx family.^[1][2] DOEF was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 2 to 3.5 mg, and the duration is listed as 12 to 16 hours.^[3] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOEF.

See also

• DOx (psychedelics)
• DOET
• DOPF
• DOTFM

References

1. Gerdes JM, Mathis CA, Shulgin AT (1988). "Synthesis of 1-[2′,5′-dimethoxy-4′-(β-fluoroethyl) phenyl]-2-aminopropane: studies related to ¹⁸F-labeled serotonin receptor ligands". Tetrahedron Letters. 29 (50): 6537–6539. doi:10.1016/S0040-4039(00)82391-6.
2. Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
3. "DOEF Entry". PiHKAL.

External links

• DOEF - Isomer Design
• DOEF - PiHKAL - Erowid
• DOEF - PiHKAL - Isomer Design
• DOEF: Here's What Little We Know - Tripsitter