2-Fluoromethamphetamine

2-Fluoromethamphetamine (2-FMA) is a stimulant drug of the amphetamine family which has been used as a designer drug .[1][2][3] 2-FMA is commonly compared to lisdexamfetamine (Vyvanse), and dextroamphetamine due to its efficacy as a study or productivity aid. 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.[4]

2-Fluoromethamphetamine
Clinical data
Routes of
administration		By mouth
Legal status
Legal status
  • CA: Schedule I[5]
  • 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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H14FN
Molar mass167.227 g·mol−1
3D model (JSmol)
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 Y
  • Key:XNWIKJYFOIDUGD-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
Not to be confused with 2-Fluoroamphetamine.

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-HT2A,[4] unlike most stimulant drugs of the amphetamine family.

Canada

As of 1996, 2-FMA is a controlled substance in Canada, due to being an analog of methamphetamine.[5]

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,[1] sale or possession of 2-FMA could be potentially be prosecuted under the Federal Analogue Act.[11]

See also

References
  1. 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): 143–56. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609.
  2. 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.
  3. Ishii, Ayumu; Sato, Kazuki; Kusakabe, Kosuke; Kato, Noriyuki; Wada, Takeshi (May 2022). "Identification and Quantitative Analysis of 2-Fluoro Methamphetamine and its Metabolites in Human Urine". Journal of Analytical Toxicology. doi:10.1093/jat/bkac026. ISSN 0146-4760. PMID 35562170.
  4. Åstrand, Anna; Guerrieri, Davide; Vikingsson, Svante; Kronstrand, Robert; Green, Henrik (23 March 2020). "In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors—On-target receptor potency and efficacy, and off-target effects". Forensic Science International. 317: 110553. doi:10.1016/j.forsciint.2020.110553.
  5. Branch, Legislative Services (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.
  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 6 September 2021. Retrieved 6 September 2021.
  11. "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.


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