Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2,5-Dimethoxy-4-fluoroamphetamine: Difference between pages

{{Short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 477211659

| IUPAC_name = 1-(4-Fluoro-2,5-dimethoxyphenyl)propan-2-amine

| tradename =

| pregnancy_category =

| legal_CA = Schedule I

| legal_UK = Class A

| legal_status =

| routes_of_administration = [[oral administration|Oral]], [[Insufflation (medicine)|Insufflation]]

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 125903-69-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 93WSW5GYR6

| ATC_suffix =

| C=11 | H=16 | F=1 | N=1 | O=2

'''2,5-Dimethoxy-4-fluoroamphetamine''' ('''DOF''') is a [[psychedelic drug|psychedelic]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] classes. [[Alexander Shulgin]] briefly describes DOF in his book ''[[PiHKAL]]'':<ref name="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}}</ref>

{{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.<ref name="pmid7143352">{{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 }}</ref>|[[Alexander Shulgin]]|([[PiHKAL]])}}

DOF showed some stimulating effects in humans, but no psychedelic activity, after three doses of 6&nbsp;mg spaced by one hour.<ref>{{cite book | title=Biochemistry and Physiology of Substance Abuse, Vol. III | publisher=CRC Press | vauthors = Nichols DE | year=1991 | location=Boca Raton, Florida}}</ref> 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 5-HT_2A receptor sufficiently.<ref>{{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 }}</ref> DOF more closely mimics the effects of the 4-unsubstituted [[Dimethoxyamphetamine|2,5-dimethoxyamphetamine]] than the effects of [[2,5-Dimethoxy-4-chloroamphetamine|DOC]], [[2,5-Dimethoxy-4-bromoamphetamine|DOB]], and [[2,5-Dimethoxy-4-iodoamphetamine|DOI]].<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref>

== See also ==

* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s

== References ==

{{Reflist}}

{{Hallucinogens}}

{{Serotonergics}}

{{Phenethylamines}}

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

[[Category:Substituted amphetamines]]

[[Category:Serotonin receptor agonists]]

[[Category:Fluoroarenes]]

[[Category:2,5-Dimethoxyphenethylamines]]