Chemistry:3-Chlorocathinone
3-Chlorocathinone (3-CC) is a psychostimulant drug of the cathinone family.[1][2][3][4] It is the analogue of the antidepressant and norepinephrine–dopamine reuptake inhibitor (NDRI) bupropion in which the N-tert-butyl group has been removed.[5][3][4] The drug is also the analogue of the stimulant 3-chloromethcathinone (3-CMC; clophedrone) in which the N-methyl group has been removed.[2][3][4]
3-CC is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).[3][4] Its EC50 values for induction of monoamine release are 64 nM for dopamine, 105 nM for norepinephrine, and 567 nM for serotonin in rat brain synaptosomes.[3][4] Hence, 3-CC shows almost 10-fold preference for induction of dopamine release over serotonin release and around 1.5-fold preference for induction of dopamine release over norepinephrine release.[3][4]
The drug was encountered as a novel designer and recreational drug by 2020.[1]
See also
- 3-Chloro-N-cyclopropylcathinone (3Cl-CpC; PAL-433, RTI-6037-39)
References
- ↑ 1.0 1.1 "NPS, PEDs and other emerging drugs on the Clearnet and the Darkweb: Use in sport". Emerging Trends in Drugs, Addictions, and Health 4. 2024. doi:10.1016/j.etdah.2024.100148.
- ↑ 2.0 2.1 "EMCDDA framework and practical guidance for naming cathinones". Drug Test Anal 16 (12): 1409–1435. December 2024. doi:10.1002/dta.3662. PMID 38389255.
- ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release". ACS Chem Neurosci 8 (6): 1397–1403. June 2017. doi:10.1021/acschemneuro.7b00055. PMID 28220701.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Shalabi AR (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. Theses and Dissertations (Thesis). Virginia Commonwealth University. doi:10.25772/M4E1-3549. Retrieved 24 November 2024 – via VCU Scholars Compass.
- ↑ "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. 69. 2014. pp. 581–620. doi:10.1016/B978-0-12-420118-7.00015-9. ISBN 978-0-12-420118-7. "Bupropion, the N-tert-butyl analog of 3-chlorocathinone, is a clinically employed antidepressant."
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