{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477211525 | drug_name = DOEF | image = DOEF chemical structure.svg | image_class = skin-invert-image | width = 250px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = 1–2 hours<ref name="PiHKAL" /><br />Peak: 3 hours<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = 12–16 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 121649-01-2 | CAS_supplemental = | PubChem = 14201982 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106293 | UNII = 72UT55MXE3 | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 123685 | NIAID_ChemDB = | PDB_ligand = | synonyms = DOEF; 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine; 4-(2-Fluoroethyl)-2,5-dimethoxyamphetamine
<!-- Chemical data --> | IUPAC_name = 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine | C=13 | H=20 | N=1 | O=2 | F=1 | SMILES = C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QLENKWFQUHHBKZ-UHFFFAOYSA-N }}
''' 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine''' ('''DOEF''') is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.<ref name="PiHKAL">{{cite web | url = http://www.erowid.org/library/books_online/pihkal/pihkal065.shtml | title = DOEF Entry | work = PiHKAL }}</ref><ref>{{cite journal | vauthors = Gerdes JM, Mathis CA, Shulgin AT | doi = 10.1016/S0040-4039(00)82391-6| title = Synthesis of 1-[2′,5′-dimethoxy-4′-(β-fluoroethyl) phenyl]-2-aminopropane: studies related to <sup>18</sup>F-labeled serotonin receptor ligands | journal = Tetrahedron Letters| volume = 29| issue = 50| pages = 6537–6539| year = 1988 }}</ref><ref>{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | year = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 }}</ref>
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists DOEF's dose as 2 to 3.5{{nbsp}}mg orally and its duration as 12 to 16{{nbsp}}hours.<ref name="PiHKAL" /> The drug's onset was 1 to 2{{nbsp}}hours and peak effects occurred after 3{{nbsp}}hours.<ref name="PiHKAL" /> 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.<ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Chemistry== ===Synthesis=== The chemical synthesis of DOEF has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of DOEF include 2C-EF, DOET, DOTFE, DOPF, and DOTFM, among others.<ref name="PiHKAL" /><ref name="Trachsel_2012">{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Test Anal | volume = 4 | issue = 7–8 | pages = 577–590 | date = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=c7b41be36b1f580a264a752521d151e6e2d9409d | url-access = subscription}}</ref><ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de }}</ref>
==History== DOEF was first described in the scientific literature by Alexander Shulgin and colleagues in 1988.<ref name="Gerdes_1988">{{cite journal | vauthors = Gerdes JM, Mathis CA, Shulgin AT | title = Synthesis of 1-[2′,5′-dimethoxy-4′-(β-fluoroethyl)phenyl]-2-aminopropane:studies related to 18F-labeled serotonin receptor ligands | journal = Tetrahedron Letters | volume = 29 | issue = 50 | pages = 6537–6539 | date = 1988 | doi = 10.1016/S0040-4039(00)82391-6 | url = https://linkinghub.elsevier.com/retrieve/pii/S0040403900823916 | access-date = 27 November 2025 | url-access = subscription }}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== DOEF is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
== See also == * DOx (psychedelics)
== References == {{Reflist}}
== External links == * [https://isomerdesign.com/pihkal/explore/65 DOEF - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal065.shtml DOEF - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/65 DOEF - PiHKAL - Isomer Design] * [https://www.bluelight.org/xf/threads/441598 The Small & Handy DOEF Thread - Bluelight] * [https://tripsitter.com/doef/ DOEF: Here's What Little We Know - Tripsitter]
{{Psychedelics}} {{Phenethylamines}}
{{DEFAULTSORT:Dimethoxy-4-(2-fluoroethyl)amphetamine, 2,5-}}
Category:DOx (psychedelics) Category:Fluoroethyl compounds Category:PiHKAL Category:Psychedelic phenethylamines