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
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Onset of action	1–2 hours; Peak: 3 hours
Duration of action	12–16 hours
Identifiers
	IUPAC name 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine;
CAS Number	121649-01-2 ;
PubChem CID	14201982;
ChemSpider	21106293 ;
UNII	72UT55MXE3;
ChEMBL	ChEMBL123685 ;
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 ; Key:QLENKWFQUHHBKZ-UHFFFAOYSA-N ;
	(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

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

Chemistry

Synthesis

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

Analogues

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

History

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

Legal status

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

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "DOEF Entry". PiHKAL.
^ 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.
^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
^ 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.
^ 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.
^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k "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.

[Trachsel_2012-4] Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.

[Trachsel_2013-5] 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.

[Gerdes_1988-6] 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.

[CDSA-7] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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