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

DOEF
Clinical data
Other namesDOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action1–2 hours
Peak: 3 hours
Duration of action12–16 hours
Identifiers
  • 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H20FNO2
Molar mass241.306 g·mol−1
3D model (JSmol)
  • C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC
  • 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 checkY
  • Key:QLENKWFQUHHBKZ-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

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

Use and effects

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.

Interactions

Chemistry

Synthesis

The chemical synthesis of DOEF has been described.

Analogues

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

History

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.

Society and culture

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

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 "DOEF Entry". PiHKAL.
  2. ↑ 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.
  3. ↑ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  4. ↑ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  5. ↑ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226.
  6. ↑ 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. Retrieved 27 November 2025.
  7. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.