2-Fluoromethcathinone
{{Technical|date=November 2024}}
{{Short description|Designer stimulant}}
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| class = Stimulant; Norepinephrine–dopamine releasing agent
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| CAS_number = 1186137-35-8
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| PubChem = 71316821
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| ChemSpiderID = 37701826
| UNII = 7NLX9J64KY
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| synonyms = 2-FMC; 2-Fluoromethylcathinone; 2-Fluoro-N-methylcathinone; 2-Flephedrone
| IUPAC_name = 1-(2-fluorophenyl)-2-(methylamino)propan-1-one
| C=10 | H=12 | F=1 | N=1 | O=1
| SMILES = CC(C(=O)C1=CC=CC=C1F)NC
| StdInChI = 1S/C10H12FNO/c1-7(12-2)10(13)8-5-3-4-6-9(8)11/h3-7,12H,1-2H3
| StdInChIKey = DCMOUMKIDLRIBO-UHFFFAOYSA-N
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2-Fluoromethcathinone (2-FMC), also known as 2-flephedrone, is a psychostimulant and designer drug of the cathinone family.{{cite journal | vauthors = Kelly JP | title = Cathinone derivatives: a review of their chemistry, pharmacology and toxicology | journal = Drug Test Anal | volume = 3 | issue = 7–8 | pages = 439–453 | date = 2011 | pmid = 21755607 | doi = 10.1002/dta.313 | url = }}{{cite book | vauthors = Glennon RA | title = Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse | chapter = Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention | series = Adv Pharmacol | volume = 69 | pages = 581–620 | date = 2014 | pmid = 24484988 | pmc = 4471862 | doi = 10.1016/B978-0-12-420118-7.00015-9 | isbn = 978-0-12-420118-7 | chapter-url = }}{{cite journal | vauthors = Kelleher C, Christie R, Lalor K, Fox J, Bowden M, O'Donnell C | title=An Overview of New Psychoactive Substances and the Outlets Supplying them | journal=Reports | date=30 June 2011 | doi=10.21427/43F1-XR91 | url=https://arrow.tudublin.ie/cserrep/23/ | access-date=24 November 2024}}{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 | url = }} It acts as a dopamine and norepinephrine releasing agent (NDRA).
Pharmacology
The drug has an {{Abbrlink|EC50|half-maximal effective concentration}} for dopamine release of 48.7{{nbsp}}nM and induces 85% release of norepinephrine at a concentration of 10{{nbsp}}μM. For comparison, the {{Abbr|EC50|half-maximal effective concentration}} values of methcathinone are 49.9{{nbsp}}nM for dopamine release and 22.4{{nbsp}}nM for norepinephrine release and it induces 100% release of norepinephrine at a concentration of 10{{nbsp}}μM.{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }} Hence, compared to methcathinone, 2-FMC appears to be relatively more selective or efficacious for induction of dopamine release over norepinephrine release. It is notable in this regard that selective dopamine releasing agents are largely unknown.{{cite journal | vauthors = Negus SS, Mello NK, Blough BE, Baumann MH, Rothman RB | title = 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 | journal = J Pharmacol Exp Ther | volume = 320 | issue = 2 | pages = 627–636 | date = February 2007 | pmid = 17071819 | doi = 10.1124/jpet.106.107383 | url = }}
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/2126 2-FMC (2-Fluoromethcathinone) - Isomer Design]
{{Stimulants}}
{{Monoamine releasing agents}}
{{Phenethylamines}}
{{DEFAULTSORT:Fluoromethcathinone, 2-}}
Category:2-Fluorophenyl compounds