2-Fluoromethamphetamine

2-Fluoromethamphetamine
Clinical data
Routes of; administration	By mouth
Legal status
Legal status	CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Unscheduled;
Identifiers
	IUPAC name (RS)-1-(2-Fluorophenyl)-N-methylpropan-2-amine;
CAS Number	1017176-48-5 ;
PubChem CID	24257263;
ChemSpider	23900072 ;
UNII	YV5793W75P;
CompTox Dashboard (EPA)	DTXSID90640530 ;
Chemical and physical data
Formula	C10H14FN
Molar mass	167.227 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=CC=C1F)NC;
	InChI InChI=1S/C10H14FN/c1-8(12-2)7-9-5-3-4-6-10(9)11/h3-6,8,12H,7H2,1-2H3 ; Key:XNWIKJYFOIDUGD-UHFFFAOYSA-N ;
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2-Fluoromethamphetamine (2-FMA) is a stimulant drug of the amphetamine family which has been used as a designer drug.^[2]^[3]^[4] 2-FMA is commonly compared to lisdexamfetamine (Vyvanse), and dextroamphetamine due to its efficacy as a study or productivity aid.^{[citation needed]} 2-FMA is purported to produce somewhat less euphoria than comparable amphetamines, likely due to its main mechanism of action consisting of norepinephrine reuptake inhibition.^[5]

Chemistry

2-Fluoromethamphetamine is fluorinated analogue of methamphetamine, and is a regioisomer of 3-FMA and 4-FMA.

It does not activate the serotonin receptors, including 5-HT_2A,^[5] 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.^[1]

China

As of October 2015, 2-FMA is a controlled substance in China.^[6]

Germany

As of 13 December 2014, 2-FMA is a controlled substance in Germany.^[7] It is controlled under Anlage I BtMG (Narcotics Act, Schedule I).^[8] 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.^[9]

Ukraine

As of July 2019, 2-FMA is a controlled substance in Ukraine (considered a narcotic).^[10]

United States

As a close analog of scheduled controlled substance,^[2] sale or possession of 2-FMA could be potentially be prosecuted under the Federal Analogue Act.^[11]

References

^ ^a ^b Legislative Services Branch (31 March 2022). "Consolidated federal laws of Canada, Controlled Drugs and Substances Act". laws-lois.justice.gc.ca. Archived from the original on 11 June 2022. Retrieved 11 August 2022.
^ ^a ^b Rösner P, Quednow B, Girreser U, Junge T (March 2005). "Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs)". Forensic Science International. 148 (2–3): 143–156. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609.
^ Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG (April 2010). "Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone". Forensic Science International. 197 (1–3): 59–66. doi:10.1016/j.forsciint.2009.12.048. PMID 20074881.
^ Ishii A, Sato K, Kusakabe K, Kato N, Wada T (February 2023). "Identification and Quantitative Analysis of 2-Fluoromethamphetamine and Its Metabolites in Human Urine". Journal of Analytical Toxicology. 47 (1): 59–65. doi:10.1093/jat/bkac026. PMID 35562170.
^ ^a ^b Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020). "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". Forensic Science International. 317: 110553. doi:10.1016/j.forsciint.2020.110553. PMID 33160102. S2CID 226279968.
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
^ Bundesgesetzblatt. "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften – Vom 5. Dezember 2014" (in German). Bundesanzeiger-Verlags-GmbH. Retrieved 6 April 2022.
^ Bundesministerium der Justiz. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) Anlage I (zu § 1 Abs. 1) (nicht verkehrsfähige Betäubungsmittel)" (in German). Retrieved 6 April 2022.
^ Bundesministerium der Justiz. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) § 29 Straftaten" (in German). Retrieved 6 April 2022.
^ "Про внесення змін до Закону України "Про обіг в Україні наркотичних засобів, психотропних речовин, їх аналогів і прекурсорів"" (in Ukrainian). Verkhovna Rada of Ukraine. 23 July 2019. Archived from the original on 5 September 2021. Retrieved 6 September 2021.
^ "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.

[:1-1] Legislative Services Branch (31 March 2022). "Consolidated federal laws of Canada, Controlled Drugs and Substances Act". laws-lois.justice.gc.ca. Archived from the original on 11 June 2022. Retrieved 11 August 2022.

[Rösner-2] Rösner P, Quednow B, Girreser U, Junge T (March 2005). "Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs)". Forensic Science International. 148 (2–3): 143–156. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609.

[3] Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG (April 2010). "Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone". Forensic Science International. 197 (1–3): 59–66. doi:10.1016/j.forsciint.2009.12.048. PMID 20074881.

[4] Ishii A, Sato K, Kusakabe K, Kato N, Wada T (February 2023). "Identification and Quantitative Analysis of 2-Fluoromethamphetamine and Its Metabolites in Human Urine". Journal of Analytical Toxicology. 47 (1): 59–65. doi:10.1093/jat/bkac026. PMID 35562170.

[:0-5] Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020). "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". Forensic Science International. 317: 110553. doi:10.1016/j.forsciint.2020.110553. PMID 33160102. S2CID 226279968.

[6] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[7] Bundesgesetzblatt. "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften – Vom 5. Dezember 2014" (in German). Bundesanzeiger-Verlags-GmbH. Retrieved 6 April 2022.

[8] Bundesministerium der Justiz. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) Anlage I (zu § 1 Abs. 1) (nicht verkehrsfähige Betäubungsmittel)" (in German). Retrieved 6 April 2022.

[9] Bundesministerium der Justiz. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz – BtMG) § 29 Straftaten" (in German). Retrieved 6 April 2022.

[10] "Про внесення змін до Закону України "Про обіг в Україні наркотичних засобів, психотропних речовин, їх аналогів і прекурсорів"" (in Ukrainian). Verkhovna Rada of Ukraine. 23 July 2019. Archived from the original on 5 September 2021. Retrieved 6 September 2021.

[:2-11] "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.

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