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

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(Redirected from2,5-Dimethoxy-4-fluoroethylamphetamine)

Pharmaceutical compound
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
PubChemCID
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
 ☒NcheckY (what is this?)  (verify)

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is apsychedelic drug pf thephenethylamine,amphetamine, andDOx families.[1][2][3] In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists DOEF's dose as 2 to 3.5 mgorally and itsduration as 12 to 16 hours.[1] The drug'sonset was 1 to 2 hours and peak effects occurred after 3 hours.[1] The effects of DOEF were reported to includeunworldliness,closed-eyeimagery no appreciableopen-eyevisuals or not highly visual,time dilation,music anderotic enhancement, nobody discomfort,insomnia, andsleep disruption, among others.[1] DOEF was first described in thescientific literature byAlexander Shulgin and colleagues in 1988.[4] Subsequently, it was described in greater detail by Shulgin inPiHKAL in 1991.[1] The drug is acontrolled substance inCanada under phenethylamine blanket-ban language.[5]

See also

[edit]

References

[edit]
  1. ^abcdefghi"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 to18F-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. ^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. Retrieved27 November 2025.
  5. ^"Controlled Drugs and Substances Act".Department of Justice Canada. Retrieved19 January 2026.

External links

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