{{Short description|Stimulant designer drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477213365 | IUPAC_name = 1-(2-Fluorophenyl)propan-2-amine | image = 2-fluoroamphetamine.svg | image_class = skin-invert-image | width = 200px | image2 = 2-Fluoroamphetamine molecule ball.png | image_class2 = bg-transparent | width2 = 200px

<!--Clinical data--> | tradename = | legal_CA = Schedule I | legal_DE = NpSG | legal_UK = Class A

<!--Identifiers--> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 1716-60-5 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = V8Q7K3989D | PubChem = 121531 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 108441

<!--Chemical data--> | C=9 | H=12 | F=1 | N=1 | smiles = CC(CC1=CC=CC=C1F)N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H12FN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = GDSXNLDTQFFIEU-UHFFFAOYSA-N }} thumb|1 gram of 2-FA

'''2-Fluoroamphetamine''' ('''2-FA''') is a stimulant drug from the amphetamine family which has been sold as a designer drug.<ref>{{cite journal | vauthors = Rösner P, Quednow B, Girreser U, Junge T | title = Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs) | journal = Forensic Science International | volume = 148 | issue = 2–3 | pages = 143–156 | date = March 2005 | pmid = 15639609 | doi = 10.1016/j.forsciint.2004.05.003 }}</ref> 2-Fluoroamphetamine differs from 3-fluoroamphetamine and 4-fluoroamphetamine in the position of the fluorine atom on the aromatic ring, making them positional isomers of one another. The replacement of a hydrogen atom with a fluorine atom in certain compounds to facilitate passage through the blood–brain barrier, as is desirable in central nervous system pharmaceutical agents, is a common practice due to the corresponding increase in lipophilicity granted by this substitution.<ref name="smartfluorine">{{cite journal | vauthors = Smart BE |title=Fluorine substituent effects on bioactivity |journal=Journal of Fluorine Chemistry |volume=109 |pages=3–11 |year=2001 |issue=1 |doi=10.1016/s0022-1139(01)00375-x |bibcode=2001JFluC.109....3S }}</ref><ref name="ismailfluorine">{{cite journal | vauthors = Ismail FM |title=Important fluorinated drugs in experimental and clinical use |journal=Journal of Fluorine Chemistry |volume=118 |issue=1–2|pages=27–33 |year=2002 |doi=10.1016/s0022-1139(02)00201-4 |bibcode=2002JFluC.118...27I }}</ref>

==Pharmacology== Anorexiant dose (amount inhibiting food intake by 50% for 2 hours, given 1 hour earlier) = 15&nbsp;mg/kg (rat; p.o.).<ref name = Costa>{{cite book | vauthors = Costa E, Garattini S | date = 1970 | title = Amphetamines and Related Compounds | page = 28 | location = New York | publisher = Raven Press }}</ref>{{Medical citation needed|date=October 2023}}

Analgesic dose (50% inhibition of response to tail-clamp) = 20&nbsp;mg/kg (mouse; i.p.).<ref name = Costa/>{{Medical citation needed|date=October 2023}}

Effect on blood pressure: 0.5&nbsp;mg/kg (rat; i.v.) produces an increase in BP of 29&nbsp;mm.<ref name = Costa/>{{Medical citation needed|date=October 2023}}

==Toxicology== LD<sub>50</sub> (mouse; i.p.) = 100&nbsp;mg/kg.<ref name = Costa/>{{Medical citation needed|date=October 2023}}

==Legal status== ===United States=== The Federal Analogue Act, 21 U.S.C. § 813, is a section of the United States Controlled Substances Act, allowing any chemical "substantially similar" to an illegal drug (in Schedule I or II) to be treated as if it were also in Schedule I or II, but only if it is intended (ref 1) for human consumption. 2-FA may be considered to be an analog of amphetamine, thus falling under the Federal Analog Act, if, as stated above, it is intended for human consumption.

===China=== As of October 2015 2-FA is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

===Finland=== Scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs" and is hence illegal.<ref>https://www.finlex.fi/fi/lainsaadanto/2008/543</ref>

== See also == * 2-Fluoromethamphetamine * 2-Methylamphetamine (2-MA) * 2-Methoxymethamphetamine (methoxyphenamine)

== References == {{Reflist}}

{{Stimulants}} {{Phenethylamines}}

{{DEFAULTSORT:Fluoroamphetamine, 2-}} Category:Substituted amphetamines Category:2-Fluorophenyl compounds Category:Designer drugs Category:Norepinephrine-dopamine releasing agents