2-Fluoromethcathinone

2-Fluoromethcathinone
Clinical data
Other names	2-FMC; 2-Fluoromethylcathinone; 2-Fluoro-N-methylcathinone; 2-Flephedrone
Drug class	Stimulant; Norepinephrine–dopamine releasing agent
Identifiers
	IUPAC name 1-(2-fluorophenyl)-2-(methylamino)propan-1-one;
CAS Number	1186137-35-8;
PubChem CID	71316821;
ChemSpider	37701826;
UNII	7NLX9J64KY;
CompTox Dashboard (EPA)	DTXSID401017070 ;
Chemical and physical data
Formula	C10H12FNO
Molar mass	181.210 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C(=O)C1=CC=CC=C1F)NC;
	InChI 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]

Pharmacology

The drug has an EC₅₀Tooltip 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]

References

^ 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 21755607.7–8&rft.pages=439-453&rft.date=2011&rft_id=info:doi/10.1002/dta.313&rft_id=info:pmid/21755607&rft.aulast=Kelly&rft.aufirst=JP&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">
^ 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 24484988.581-620&rft.date=2014&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4471862#id-name=PMC&rft_id=info:pmid/24484988&rft_id=info:doi/10.1016/B978-0-12-420118-7.00015-9&rft.isbn=978-0-12-420118-7&rft.aulast=Glennon&rft.aufirst=RA&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">
^ 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.
^ ^a ^b ^c ^d ^e ^f 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 30341459.915-924&rft.date=2019-03&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6475490#id-name=PMC&rft_id=info:pmid/30341459&rft_id=info:doi/10.1007/s00213-018-5063-9&rft.aulast=Blough&rft.aufirst=BE&rft.au=Decker, AM&rft.au=Landavazo, A&rft.au=Namjoshi, OA&rft.au=Partilla, JS&rft.au=Baumann, MH&rft.au=Rothman, RB&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6475490&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">
^ ^a ^b 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.305-320&rft.pub=Wiley&rft.date=2008-07&rft_id=info:oclcnum/181862653&rft_id=https://openlibrary.org/works/OL18589888W#id-name=OL&rft.isbn=978-0-470-11790-3&rft.aulast=Blough&rft.aufirst=B&rft_id=https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">
^ 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 17071819.627-636&rft.date=2007-02&rft_id=info:doi/10.1124/jpet.106.107383&rft_id=info:pmid/17071819&rft.aulast=Negus&rft.aufirst=SS&rft.au=Mello, NK&rft.au=Blough, BE&rft.au=Baumann, MH&rft.au=Rothman, RB&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

External links

2-FMC (2-Fluoromethcathinone) - Isomer Design

[Kelly2011-1] 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 21755607.7–8&rft.pages=439-453&rft.date=2011&rft_id=info:doi/10.1002/dta.313&rft_id=info:pmid/21755607&rft.aulast=Kelly&rft.aufirst=JP&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

[Glennon2014-2] 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 24484988.581-620&rft.date=2014&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4471862#id-name=PMC&rft_id=info:pmid/24484988&rft_id=info:doi/10.1016/B978-0-12-420118-7.00015-9&rft.isbn=978-0-12-420118-7&rft.aulast=Glennon&rft.aufirst=RA&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

[KelleherChristieLalor2011-3] 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.

[BloughDeckerLandavazo2019-4] ^ ^a ^b ^c ^d ^e ^f 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 30341459.915-924&rft.date=2019-03&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6475490#id-name=PMC&rft_id=info:pmid/30341459&rft_id=info:doi/10.1007/s00213-018-5063-9&rft.aulast=Blough&rft.aufirst=BE&rft.au=Decker, AM&rft.au=Landavazo, A&rft.au=Namjoshi, OA&rft.au=Partilla, JS&rft.au=Baumann, MH&rft.au=Rothman, RB&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6475490&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

[Blough2008-5] 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.305-320&rft.pub=Wiley&rft.date=2008-07&rft_id=info:oclcnum/181862653&rft_id=https://openlibrary.org/works/OL18589888W#id-name=OL&rft.isbn=978-0-470-11790-3&rft.aulast=Blough&rft.aufirst=B&rft_id=https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

[NegusMelloBlough2007-6] 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 17071819.627-636&rft.date=2007-02&rft_id=info:doi/10.1124/jpet.106.107383&rft_id=info:pmid/17071819&rft.aulast=Negus&rft.aufirst=SS&rft.au=Mello, NK&rft.au=Blough, BE&rft.au=Baumann, MH&rft.au=Rothman, RB&rfr_id=info:sid/en.wikipedia.org:2-Fluoromethcathinone" class="Z3988">

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2-Fluoromethcathinone

Contents

Pharmacology

See also

References

External links