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

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DOEF
Clinical data
Other namesDOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action1–2 hours[1]
Peak: 3 hours[1]
Duration of action12–16 hours[1]
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.[1][2][3]

Use and effects

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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]

Interactions

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Chemistry

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Synthesis

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The chemical synthesis of DOEF has been described.[1]

Analogues

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Analogues of DOEF include 2C-EF, DOET, DOTFE, DOPF, and DOTFM, among others.[1][4][5]

History

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DOEF was first described in the scientific literature by Alexander Shulgin and colleagues in 1988.[6] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

Society and culture

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DOEF is a controlled substance in Canada under phenethylamine blanket-ban language.[7]

See also

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References

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  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.
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