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

vanc 6 changed changed 477211525 DOEF DOEF chemical structure.svg skin-invert-image 250px Oral Serotonergic psychedelic; Hallucinogen None 1–2 hoursPeak: 3 hours 12–16 hours correct CAS 121649-01-2 14201982 correct chemspider 21106293 72UT55MXE3 correct EBI 123685 DOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine 13 20 1 2 1 C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC correct chemspider 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 correct chemspider QLENKWFQUHHBKZ-UHFFFAOYSA-N 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. http://www.erowid.org/library/books_online/pihkal/pihkal065.shtml DOEF Entry PiHKAL Gerdes JM, Mathis CA, Shulgin AT 10.1016/S0040-4039(00)82391-6 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 1988 Trachsel D Fluorine in psychedelic phenethylamines Drug Testing and Analysis 4 7–8 577–590 2012 22374819 10.1002/dta.413 Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DOEF's dose as 2 to 3.5mg orally and its duration as 12 to 16hours. The drug's onset was 1 to 2hours and peak effects occurred after 3hours. 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 Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Chemistry Synthesis The chemical synthesis of DOEF has been described. Analogues Analogues of DOEF include 2C-EF, DOET, DOTFE, DOPF, and DOTFM, among others. Trachsel D Fluorine in psychedelic phenethylamines Drug Test Anal 4 7–8 577–590 2012 22374819 10.1002/dta.413 https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=c7b41be36b1f580a264a752521d151e6e2d9409d subscription Trachsel D, Lehmann D, Enzensperger C Phenethylamine: von der Struktur zur Funktion Solothurn 2013 Phenethylamines: From Structure to Function 1 Nachtschatten-Verlag Nachtschatten-Science 978-3-03788-700-4 858805226 https://books.google.com/books?id=-Us1kgEACAAJ de History DOEF was first described in the scientific literature by Alexander Shulgin and colleagues in 1988. Gerdes JM, Mathis CA, Shulgin AT 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 1988 10.1016/S0040-4039(00)82391-6 https://linkinghub.elsevier.com/retrieve/pii/S0040403900823916 27 November 2025 subscription Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991. Society and culture Legal status DOEF is a controlled substance in Canada under phenethylamine blanket-ban language.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 See also DOx (psychedelics) References External links DOEF - Isomer Design DOEF - PiHKAL - Erowid DOEF - PiHKAL - Isomer Design The Small & Handy DOEF Thread - Bluelight DOEF: Here's What Little We Know - Tripsitter Category:DOx (psychedelics) Category:Fluoroethyl compounds Category:PiHKAL Category:Psychedelic phenethylamines