2-Fluoromethcathinone

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2-Fluoromethcathinone
2-Fluoromethcathinone.svg
Clinical data
Other names2-FMC; 2-Fluoromethylcathinone; 2-Fluoro-N-methylcathinone; 2-Flephedrone
Drug class Stimulant; Norepinephrine–dopamine releasing agent
Identifiers
  • 1-(2-fluorophenyl)-2-(methylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H12FNO
Molar mass 181.210 g·mol−1
3D model (JSmol)
  • CC(C(=O)C1=CC=CC=C1F)NC
  • InChI=1S/C10H12FNO/c1-7(12-2)10(13)8-5-3-4-6-9(8)11/h3-7,12H,1-2H3
  • Key:DCMOUMKIDLRIBO-UHFFFAOYSA-N

2-Fluoromethcathinone (2-FMC), also known as 2-flephedrone, is a psychostimulant and designer drug of the cathinone family. [1] [2] [3] [4] It acts as a dopamine and norepinephrine releasing agent (NDRA). [4]

Contents

Pharmacology

The drug has an EC50 Tooltip half-maximal effective concentration for dopamine release of 48.7 nM and induces 85% release of norepinephrine at a concentration of 10 μM. [4] For comparison, the EC50 values of methcathinone are 49.9 nM for dopamine release and 22.4 nM for norepinephrine release and it induces 100% release of norepinephrine at a concentration of 10 μM. [4] [5] Hence, compared to methcathinone, 2-FMC appears to be relatively more selective or efficacious for induction of dopamine release over norepinephrine release. [4] [5] It is notable in this regard that selective dopamine releasing agents are largely unknown. [6] [4]

See also

Related Research Articles

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

Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis, also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

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<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters.

<span class="mw-page-title-main">Norepinephrine releasing agent</span> Catecholaminergic type of drug

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<span class="mw-page-title-main">Dopamine releasing agent</span> Type of drug

A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain.

<span class="mw-page-title-main">Norepinephrine–dopamine releasing agent</span> Drug class

A norepinephrine–dopamine releasing agent (NDRA) is a type of drug which induces the release of norepinephrine and dopamine in the body and/or brain.

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<span class="mw-page-title-main">BK-NM-AMT</span> Monoamine releaser and entactogen

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References

  1. ↑ Kelly JP (2011). "Cathinone derivatives: a review of their chemistry, pharmacology and toxicology". Drug Test Anal. 3 (7–8): 439–453. doi:10.1002/dta.313. PMID   21755607.
  2. ↑ Glennon RA (2014). "Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention". Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Adv Pharmacol. Vol. 69. pp. 581–620. doi:10.1016/B978-0-12-420118-7.00015-9. ISBN   978-0-12-420118-7. PMC   4471862 . PMID   24484988.
  3. ↑ Kelleher C, Christie R, Lalor K, Fox J, Bowden M, O'Donnell C (30 June 2011). "An Overview of New Psychoactive Substances and the Outlets Supplying them". Reports. doi:10.21427/43F1-XR91 . Retrieved 24 November 2024.
  4. 1 2 3 4 5 6 Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, et al. (March 2019). "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl). 236 (3): 915–924. doi:10.1007/s00213-018-5063-9. PMC   6475490 . PMID   30341459.
  5. 1 2 Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN   978-0-470-11790-3. OCLC   181862653. OL   18589888W.
  6. ↑ Negus SS, Mello NK, Blough BE, Baumann MH, Rothman RB (February 2007). "Monoamine releasers with varying selectivity for dopamine/norepinephrine versus serotonin release as candidate "agonist" medications for cocaine dependence: studies in assays of cocaine discrimination and cocaine self-administration in rhesus monkeys". J Pharmacol Exp Ther. 320 (2): 627–636. doi:10.1124/jpet.106.107383. PMID   17071819.
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