Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Fluoromethamphetamine: Difference between pages

{{Short description|Stimulant designer drug}}

{{cs1 config|name-list-style=vanc}}

{{Distinguish|2-Fluoroamphetamine}}

{{Use dmy dates|date=July 2022}}

'''2-Fluoromethamphetamine''' ('''2-FMA''') is a [[stimulant]] drug of the [[amphetamine]] family which has been used as a [[designer drug]].<ref name="Rösner"/><ref>{{cite journal | vauthors = Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG | title = Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone | journal = Forensic Science International | volume = 197 | issue = 1–3 | pages = 59–66 | date = April 2010 | pmid = 20074881 | doi = 10.1016/j.forsciint.2009.12.048 }}</ref><ref>{{cite journal | vauthors = Ishii A, Sato K, Kusakabe K, Kato N, Wada T | title = Identification and Quantitative Analysis of 2-Fluoromethamphetamine and Its Metabolites in Human Urine | journal = Journal of Analytical Toxicology | volume = 47 | issue = 1 | pages = 59–65 | date = February 2023 | pmid = 35562170 | doi = 10.1093/jat/bkac026 }}</ref> 2-FMA is commonly compared to [[lisdexamfetamine]] (Vyvanse), and [[dextroamphetamine]] due to its efficacy as a study or productivity aid.{{Citation needed|reason=This is available online and anecdotally, but has not been published in a scientific journal to my knowledge. |date=May 2021}} 2-FMA is purported to produce somewhat less euphoria than comparable amphetamines, likely due to its main mechanism of action consisting of [[Norepinephrine reuptake inhibitor|norepinephrine reuptake inhibition]].<ref name=":0">{{cite journal | vauthors = Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H | title = In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT_1A, and 5-HT_2A receptors-On-target receptor potency and efficacy, and off-target effects | journal = Forensic Science International | volume = 317 | pages = 110553 | date = December 2020 | pmid = 33160102 | doi = 10.1016/j.forsciint.2020.110553 | s2cid = 226279968 | doi-access = free }}</ref>

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477213403

| IUPAC_name = (''RS'')-1-(2-Fluorophenyl)-''N''-methylpropan-2-amine

| image = 2-Fluoro Methamphetamine Structure.svg

| image2 = 2-Fluoromethamphetamine molecule ball.png

| alt2 = Ball-and-stick model of the 2-fluoromethamphetamine molecule

<!--Clinical data-->| tradename =

| routes_of_administration = [[Oral administration|By mouth]]

| legal_US = Unscheduled

| legal_CA = Schedule I<ref name=":1" />

| legal_UK = Class A

| legal_DE = Anlage I

<!--Identifiers-->| PubChem = 24257263

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = YV5793W75P

| CAS_number_Ref = {{cascite|changed|CAS}}

| CAS_number = 1017176-48-5

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 23900072

<!--Chemical data-->| C = 10

| H = 14

| F = 1

| N = 1

| smiles = CC(CC1=CC=CC=C1F)NC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H14FN/c1-8(12-2)7-9-5-3-4-6-10(9)11/h3-6,8,12H,7H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XNWIKJYFOIDUGD-UHFFFAOYSA-N

== Chemistry ==

2-Fluoromethamphetamine is fluorinated analogue of [[methamphetamine]], and is a [[Structural isomer#Regioisomer|regioisomer]] of [[3-FMA]] and [[4-FMA]].

It does not activate the serotonin receptors, including [[5-HT2A receptor|5-HT_2A]],<ref name=":0" /> unlike most stimulant drugs of the amphetamine family.

==Legal status==

=== Canada ===

As of 1996, 2-FMA is a controlled substance in Canada, due to being an analog of [[methamphetamine]].<ref name=":1">{{Cite web | author = Legislative Services Branch |date=2022-03-31 |title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act |url=https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-9.html |url-status=live |archive-url=https://web.archive.org/web/20220611233323/https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-9.html |archive-date=2022-06-11 |access-date=2022-08-11 |website=laws-lois.justice.gc.ca}}</ref>

===China===

As of October 2015, 2-FMA 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=Chinese | 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>

===Germany===

As of 13 December 2014, 2-FMA is a controlled substance in Germany.<ref>{{cite web |last1=Bundesgesetzblatt |title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften – Vom 5. Dezember 2014 |url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1649260007019 |language=German |publisher=Bundesanzeiger-Verlags-GmbH |access-date=6 April 2022}}</ref> It is controlled under Anlage I BtMG (Narcotics Act, Schedule I).<ref>{{cite web |last1=Bundesministerium der Justiz |title=Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) Anlage I (zu § 1 Abs. 1) (nicht verkehrsfähige Betäubungsmittel) |url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html |language=German |access-date=6 April 2022}}</ref> Substances controlled under Anlage I BtMG are illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license. Violations of the law are punishable by a fine or imprisonment for up to five years.<ref>{{cite web |last1=Bundesministerium der Justiz |title=Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) § 29 Straftaten |url=https://www.gesetze-im-internet.de/btmg_1981/__29.html |language=German |access-date=6 April 2022}}</ref>

===Ukraine===

As of July 2019, 2-FMA is a controlled substance in Ukraine (considered a narcotic).<ref>{{cite web | url=https://zakon.rada.gov.ua/laws/show/600-2019-%D0%BF | title=Про внесення змін до Закону України "Про обіг в Україні наркотичних засобів, психотропних речовин, їх аналогів і прекурсорів" | publisher=Verkhovna Rada of Ukraine | date=23 July 2019 | language=Ukrainian | access-date=6 September 2021 | archive-url=https://web.archive.org/web/20210905235904/https://zakon.rada.gov.ua/laws/show/863-14| archive-date=5 September 2021 | url-status=live }}</ref>

=== United States ===

As a close analog of [[Controlled Substances Act#Schedules of controlled substances|scheduled]] [[controlled substance]],<ref name="Rösner">{{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> sale or [[Drug possession|possession]] of 2-FMA could be potentially be prosecuted under the [[Federal Analogue Act]].<ref name=":2">{{cite web |title=Federal Controlled Substance Analogue Act Summary |url=https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml |work=Erowid Analog Law Vault}}</ref>

== See also ==

* [[2-Fluoroamphetamine]]

* [[3-Fluoromethamphetamine]]

* [[3-Fluoroethamphetamine]]

* [[4-Fluoromethamphetamine]]

* [[4-FA|4-Fluoroamphetamine]]

* [[Methoxyphenamine|2-Methoxymethamphetamine]] (methoxyphenamine)

* [[2F-MAR]]

== References ==

{{Reflist}}

{{Stimulants}}

{{Phenethylamines}}

{{DEFAULTSORT:Fluoromethamphetamine, 2-}}

[[Category:Designer drugs]]

[[Category:Methamphetamines]]

[[Category:2-Fluorophenyl compounds]]

[[Category:Norepinephrine-dopamine releasing agents]]

[[Category:Organofluorides]]