2,5-Dimethoxy-4-fluoroamphetamine

Alexander Shulgin briefly describes DOF in his book PiHKAL:{{cite book | title = PiHKAL: A Chemical Love Story | vauthors = Shulgin A, Shulgin A | publisher = Transform Press | location = United States | isbn = 978-0-9630096-0-9 | pages = 978 | url = http://www.erowid.org/library/books_online/pihkal/pihkal.shtml |date= September 1991}}

{{Quotation|Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.{{cite journal | vauthors = Glennon RA, Young R, Benington F, Morin RD | title = Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 10 | pages = 1163–1168 | date = October 1982 | pmid = 7143352 | doi = 10.1021/jm00352a013 }}|Alexander Shulgin|(PiHKAL)}}

DOF showed some stimulating effects in humans, but no psychedelic activity, after three doses of 6 mg spaced by one hour.{{cite book | vauthors=Nichols DE, Oberlender R, McKenna DJ | chapter=Stereochemical Aspects of Hallucinogenesis | veditors=Watson RR | title=Biochemistry and Physiology of Substance Abuse | volume=3 | publisher=CRC Press | publication-place=Boca Raton, Fla. | year=1991 | isbn=978-0-8493-4463-3 | oclc=26748320 | pages=1–39 | url=https://books.google.com/books?id=Zl4vAAAACAAJ | chapter-url=https://archive.org/details/biochemistryphys0003unse/page/1/mode/2up}} Researcher Daniel Trachsel further suspected that the molar refraction of the important 4-substituent in DOF and 2C-F may be too low to activate the serotonin 5-HT_2A receptor sufficiently to produce psychedelic effects.{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | date = July 2012 | pmid = 22374819 | doi = 10.1002/dta.413 }} DOF more closely mimics the effects of the 4-unsubstituted 2,5-dimethoxyamphetamine than the effects of DOC, DOB, and DOI.{{cite journal | vauthors = Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, Nash JF | title = 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist | journal = Journal of Medicinal Chemistry | volume = 37 | issue = 25 | pages = 4346–4351 | date = December 1994 | pmid = 7996545 | doi = 10.1021/jm00051a011 }}{{cite journal | vauthors = Glennon RA | title = Discriminative stimulus properties of hallucinogens and related designer drugs | journal = NIDA Research Monograph | volume = 116 | issue = 116 | pages = 25–44 | year = 1991 | pmid = 1369672 | url = http://archives.drugabuse.gov/pdf/monographs/download116.html | access-date = 2015-06-29 | url-status = dead | archive-url = https://web.archive.org/web/20150722190934/http://archives.drugabuse.gov/pdf/monographs/download116.html | archive-date = 2015-07-22 }}{{cite journal | vauthors = Johnson MP, Hoffman AJ, Nichols DE, Mathis CA | title = Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI | journal = Neuropharmacology | volume = 26 | issue = 12 | pages = 1803–1806 | date = December 1987 | pmid = 3437942 | doi = 10.1016/0028-3908(87)90138-9 | s2cid = 25077839 }}

The receptor and transporter interactions of DOF have been characterized.{{cite journal | vauthors = Shannon M, Battaglia G, Glennon RA, Titeler M | title = 5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA) | journal = Eur J Pharmacol | volume = 102 | issue = 1 | pages = 23–29 | date = June 1984 | pmid = 6479216 | doi = 10.1016/0014-2999(84)90333-9 | url = }}{{cite journal | vauthors = Glennon RA | title = Central serotonin receptors as targets for drug research | journal = J Med Chem | volume = 30 | issue = 1 | pages = 1–12 | date = January 1987 | pmid = 3543362 | doi = 10.1021/jm00384a001 | url = | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites}}{{cite journal | vauthors = Nelson DL, Lucaites VL, Wainscott DB, Glennon RA | title = Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors | journal = Naunyn Schmiedebergs Arch Pharmacol | volume = 359 | issue = 1 | pages = 1–6 | date = January 1999 | pmid = 9933142 | doi = 10.1007/pl00005315 | url = }}{{cite journal | vauthors = Rudin D, Luethi D, Hoener MC, Liechti ME | title=Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2121 | doi-access=free | url=https://www.researchgate.net/publication/360423277_Structure-activity_relation_of_halogenated_25-dimethoxyamphetamines_compared_to_their_a-desmethyl_2C_analogues}} As with other DOx drugs, it shows affinity for the serotonin 5-HT₂ receptors and acts as a partial to full agonist of the serotonin 5-HT_2A and 5-HT_2B receptors. However, it shows much lower affinity for the serotonin 5-HT₂ receptors than many other DOx drugs and a much lower degree of selectivity for the serotonin 5-HT_2A receptor over the serotonin 5-HT_1A receptor. On the other hand, the activational potencies of DOF at the serotonin 5-HT_2A and 5-HT_2B receptors was similar to those of DOB. The drug lacks significant affinity for the monoamine transporters (MATs), the human trace amine-associated receptor 1 (TAAR1), and various other receptors.

DOF substituted for DOM in rodent drug discrimination tests, albeit with lower potency than other DOx drugs.{{cite journal | vauthors = Glennon RA | title = Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships | journal = NIDA Res Monogr | volume = 94 | issue = | pages = 43–67 | date = 1989 | pmid = 2575229 | doi = | url = }}

• 2,5-Dimethoxy-4-substituted amphetamines (DOx)
• 2C-F
• 25F-NBOMe

{{Reflist}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

{{DEFAULTSORT:Dimethoxy-4-fluoroamphetamine, 2,5-}}

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:DOx (psychedelics)

Category:Fluoroarenes

Category:Serotonin receptor agonists

Category:Substituted amphetamines