2-Fluoromethamphetamine

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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.[ 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. [4]

Contents

2-Fluoromethamphetamine
2-Fluoro Methamphetamine Structure.svg
2-Fluoromethamphetamine molecule ball.png
Clinical data
Routes of
administration
By mouth
Legal status
Legal status
Identifiers
  • (RS)-1-(2-Fluorophenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H14FN
Molar mass 167.227 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=CC=C1F)NC
  • InChI=1S/C10H14FN/c1-8(12-2)7-9-5-3-4-6-10(9)11/h3-6,8,12H,7H2,1-2H3 Yes check.svgY
  • Key:XNWIKJYFOIDUGD-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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

Related Research Articles

<span class="mw-page-title-main">4-Fluoroamphetamine</span> Psychoactive research chemical

4-Fluoroamphetamine, also known as para-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.

<span class="mw-page-title-main">4-Fluoromethamphetamine</span> Stimulant designer drug

4-Fluoromethamphetamine (4-FMA) is a stimulant drug related to methamphetamine and 4-fluoroamphetamine. It has been reported to be sold as a designer drug, but little is known about its pharmacology or toxicology. It was first detected from legal highs sold in Japan in 2006 and became illegal to sell or to possess for the purpose of distribution in Japan in 2008. It was initially reported to be contained as an ingredient in some of the range of party pills sold internationally by the Israeli company Neorganics from around 2006 onwards, but this was later shown to be incorrect and this ingredient was eventually identified as the closely related compound 2-fluoromethamphetamine.

<span class="mw-page-title-main">Ethcathinone</span> Simulant designer drug

Ethcathinone, also known as ethylpropion or ETH-CAT, is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is an active metabolite of the prodrug diethylcathinone and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills", and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">2-Fluoroamphetamine</span> Stimulant designer drug

2-Fluoroamphetamine (2-FA) is a stimulant drug from the amphetamine family which has been sold as a designer drug. 2-Fluoroamphetamine differs from 3- 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.

<span class="mw-page-title-main">3-Fluoromethamphetamine</span> Stimulant designer drug

3-Fluoromethamphetamine (3-FMA) is a stimulant drug related to methamphetamine and 3-fluoroamphetamine. It has been sold online as a designer drug.

<span class="mw-page-title-main">AB-FUBINACA</span> Chemical compound

AB-FUBINACA (AMB-FUBINACA) is a psychoactive drug that acts as a potent agonist for the cannabinoid receptors, with Ki values of 0.9 nM at CB1 and 23.2 nM at CB2 and EC50 values of 1.8 nM at CB1 and 3.2 nM at CB2. It was originally developed by Pfizer in 2009 as an analgesic medication but was never pursued for human use. In 2012, it was discovered as an ingredient in synthetic cannabinoid blends in Japan, along with a related compound AB-PINACA, which had not previously been reported.

<span class="mw-page-title-main">AB-PINACA</span> Chemical compound

AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.

<span class="mw-page-title-main">4,4'-Dimethylaminorex</span> Chemical compound

4,4'-Dimethylaminorex, sometimes referred to by the street name "Serotoni", is a psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex, and pemoline. It was first detected in the Netherlands in December 2012, and has been sold as a designer drug around Europe since mid-2013.

<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most countries that have banned mephedrone due to 3-MMC being a structural isomer of 4-MMC. However, 3-MMC has still appeared on the recreational drug market as an alternative to mephedrone, and was first identified being sold in Sweden in 2012. Unlike some synthetic cathinones, 3-MMC has been evaluated in at least one large mammal study. 3-MMC is a monoamine transporter substrate that potently inhibits norepinephrine uptake and displays more pronounced dopaminergic vs. serotonergic activity.

<span class="mw-page-title-main">AB-CHMINACA</span> Chemical compound

AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent. Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.

<span class="mw-page-title-main">THJ-2201</span> Synthetic cannabinoid

THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor and has been sold online as a designer drug.

<span class="mw-page-title-main">5F-AMB</span> Chemical compound

5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in early 2014. Although only very little pharmacological information about 5F-AMB itself exists, its 4-cyanobutyl analogue (instead of 5-fluoropentyl) has been reported to be a potent agonist for the CB1 receptor (KI = 0.7 nM).

Drugs controlled by the German Betäubungsmittelgesetz (BtMG). Trade and possession of these substances without licence or prescription is considered illegal; prescription is illegal for drugs on Anlage I and II and drugs on Anlage III require a special prescription form.

<span class="mw-page-title-main">5F-AB-PINACA</span> Chemical compound

5F-AB-PINACA is an indazole-based synthetic cannabinoid that is derived from a series of compounds originally developed by Pfizer in 2009 as an analgesic medication, and has been sold online as a designer drug.

<span class="mw-page-title-main">THJ-018</span> Chemical compound

THJ-018 (SGT-17) is a synthetic cannabinoid that is the indazole analogue of JWH-018 and has been sold online as a designer drug.

<span class="mw-page-title-main">NM-2201</span> Chemical compound

NM-2201 (also known as CBL-2201 and NA-5F-PIC) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low nanomolar affinity.

<i>para</i>-Chloromethamphetamine Chemical compound

para-Chloromethamphetamine is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-chloroamphetamine (4-CA). It has been found to decrease serotonin in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.

<span class="mw-page-title-main">4-Chloromethcathinone</span> Simulant drug of the cathinone class

4-Chloromethcathinone is a stimulant drug of the cathinone class that has been sold online as a designer drug.

<span class="mw-page-title-main">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

References

  1. 1 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.
  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 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.
  4. 1 2 Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 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 . PMID   33160102. S2CID   226279968.
  5. 1 2 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.
  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.
  11. "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.