4-Fluoromethamphetamine

Last updated
4-Fluoromethamphetamine
4-FMA.svg
4-Fluoromethamphetamine molecule ball.png
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA:Schedule I [1]
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class A
  • US:Unscheduled
Identifiers
  • (RS)-1-(4-Fluorophenyl)-N-methylpropan-2-amine
CAS Number
  • 351-03-1  X mark.svgN
    52063-62-4 (hydrochloride)
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.254.220 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H14FN
Molar mass 167.227 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)CC(NC)C
  • InChI=1S/C10H14FN/c1-8(12-2)7-9-3-5-10(11)6-4-9/h3-6,8,12H,7H2,1-2H3 Yes check.svgY
  • Key:YCWZPIHKUYZTFM-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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. [2] 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 (although not to simply possess for personal use) in Japan in 2008. [3] 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. [4]

Contents

Pharmacology

4-FMA is a CYP450 inhibitor. It reduces the metabolism of methamphetamine, which has the effect of increasing its potency, duration and systemic toxicity while also reducing its cellular toxicity. [5]

Australia

4-FMA is considered a Schedule 9 substance in Australia under the Poisons Standard (October 2015). [6] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. [6]

Canada

As of 1996, 4-FMA is a controlled substance in Canada, due to being an analog of methamphetamine. [1]

China

As of October 2015 4-FMA is a controlled substance in China. [7]

United States

As a close analog of scheduled controlled substance, [2] sale or possession of 4-FMA could be potentially be prosecuted under the Federal Analogue Act. [8]

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">Betahydroxythiofentanyl</span> Chemical compound

Betahydroxythiofentanyl (β-hydroxythiofentanyl) is an opioid analgesic that is an analog of fentanyl. Beginning as early as 2008, clandestine labs in China began to manufacture synthetic opioids on an industrial scale. Initially, these opioids were distributed in Eastern European markets such as Ukraine and Estonia. Beginning in 2015, fentanyl had replaced heroin as the opioid of choice due to its cheap cost of production and astronomical potency. Utilizing loosely regulated drug laws in the ports of western Mexico, Mexican and Chinese criminal organizations began to traffic the drug en masse along the U.S.-Mexico border.

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

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">Flephedrone</span> Chemical compound

Flephedrone, also known as 4-fluoromethcathinone (4-FMC), is a stimulant drug of the cathinone chemical class that has been sold online as a designer drug starting in 2008.

<i>alpha</i>-Pyrrolidinopentiophenone Chemical compound

α-Pyrrolidinopentiophenone is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug. Colloquially, it is sometimes called flakka. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.

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

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">2-Fluoromethamphetamine</span> Stimulant designer drug

2-Fluoromethamphetamine (2-FMA) is a stimulant drug of the amphetamine family which has been used as a designer drug. 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.

<span class="mw-page-title-main">JWH-122</span> Chemical compound

JWH-122 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is a methylated analogue of JWH-018. It has a Ki of 0.69 nM at CB1 and 1.2 nM at CB2.

<span class="mw-page-title-main">AH-7921</span> Opioid analgesic

AH-7921 is an opioid analgesic drug selective for the μ-opioid receptor, having around 90% the potency of morphine when administered orally. It was discovered in the 1970s by a team at Allen and Hanburys located in the United Kingdom. The drug is considered a new psychoactive substance (NPS) in which it is synthetically created in laboratories to mimic that of controlled substances. The substance has also been sold on the internet since 2012 as a "research chemical". When sold online it may be called the alternative name doxylam, not to be confused with doxylamine. AH-7921 has never progressed to clinical trials. The DEA is not aware of any medical usage in the United States, and has not insisted the Health and Human Services department (HHS) to conduct any medical research of the substance's uses.

<span class="mw-page-title-main">25C-NBOMe</span> Psychedelic drug

25C-NBOMe is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011. It acts as a potent agonist of the 5HT2A receptor, and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET). Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

<span class="mw-page-title-main">Pentedrone</span> Stimulant designer drug of the cathinone class

Pentedrone is a stimulant of the cathinone class that has been sold as a designer drug and has been found since 2010 as an ingredient in a number of "bath salt" mixes sold as legal highs.

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

EAM-2201 is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in synthetic cannabis smoking blends Like the closely related MAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by designer drug suppliers specifically for recreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds JWH-210 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

<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">25D-NBOMe</span> Chemical compound

25D-NBOMe is a derivative of the phenethylamine derived hallucinogen 2C-D. It acts in a similar manner to related compounds such as 25I-NBOMe, which is a potent agonist at the 5HT2A receptor. 25D-NBOMe has been sold as a street drug since 2010 and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe. It was banned as a Temporary Class Drug in the UK on 10 June 2013 after concerns about its recreational use.

<span class="mw-page-title-main">Acetylfentanyl</span> Opioid analgesic

Acetylfentanyl is an opioid analgesic drug that is an analog of fentanyl. Studies have estimated acetylfentanyl to be fifteen times more potent than morphine, which would mean that despite being somewhat weaker than fentanyl, it is nevertheless still several times stronger than pure heroin. It has never been licensed for medical use and instead has only been sold as a designer drug. Acetylfentanyl was discovered at the same time as fentanyl itself and had only rarely been encountered on the illicit market in the late 1980s. However, in 2013, Canadian police seized 3 kilograms of acetylfentanyl. As a μ-opioid receptor agonist, acetylfentanyl may serve as a direct substitute for heroin or other opioids. Common side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.

<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).

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

5F-APINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding pentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.

<span class="mw-page-title-main">4-Chloromethcathinone</span> Pair of enantiomers

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">3-Chloromethcathinone</span> Chemical compound

3-Chloromethcathinone is a stimulant drug of the cathinone class that has been sold online as a designer drug, mainly in European countries such as Ireland, Italy, Poland and Sweden.

References

  1. 1 2 Branch, Legislative Services (2022-03-31). "Consolidated federal laws of Canada, Controlled Drugs and Substances Act". laws-lois.justice.gc.ca. Archived from the original on 2022-06-11. Retrieved 2022-08-11.
  2. 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): 143–56. doi:10.1016/j.forsciint.2004.05.003. PMID   15639609.
  3. Nagashima M, Seto T, Takahashi M, Suzuki J, Yasuda I (2006). "Spectrum Data of the 3rd Governor-designated Drugs and the Analyses of Uncontrolled Drugs Purchased" (PDF). Tokyo Metropolitan Institute of Public Health Annual Report (in Japanese). 57: 109–113. Archived from the original (PDF) on 2011-07-22. Retrieved 2007-12-10.
  4. 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.
  5. Cherner M, Bousman C, Everall I, Barron D, Letendre S, Vaida F, et al. (September 2010). "Cytochrome P450-2D6 extensive metabolizers are more vulnerable to methamphetamine-associated neurocognitive impairment: preliminary findings". Journal of the International Neuropsychological Society. 16 (5): 890–901. doi:10.1017/S1355617710000779. PMC   3543816 . PMID   20727252.
  6. 1 2 "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.
  7. "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.
  8. "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault.