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Other names | 3-CC; Norclophedrone; 3Cl-C; 3Cl-Cathinone; 3-Chloro-β-ketoamphetamine |
Drug class | Stimulant; Serotonin–norepinephrine–dopamine releasing agent |
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Formula | C9H10ClNO |
Molar mass | 183.64 g·mol |
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3-Chlorocathinone (3-CC) is a psychostimulant drug of the cathinone family. It is the analogue of the antidepressant bupropion in which the N-tert-butyl group has been removed. The drug is also the analogue of the stimulant 3-chloromethcathinone (3-CMC; clophedrone) in which the N-methyl group has been removed.
3-CC is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 64 nM for dopamine, 105 nM for norepinephrine, and 567 nM for serotonin in rat brain synaptosomes. Hence, 3-CC shows almost 10-fold preference for induction of dopamine release over induction of serotonin release.
The drug was encountered as a novel designer and recreational drug by 2020.
References
- ^ Mazzoni, Irene; Rabin, Olivier (2024). "NPS, PEDs and other emerging drugs on the Clearnet and the Darkweb: Use in sport". Emerging Trends in Drugs, Addictions, and Health. 4: 100148. doi:10.1016/j.etdah.2024.100148.
- ^ Pulver B, Fischmann S, Gallegos A, Christie R (December 2024). "EMCDDA framework and practical guidance for naming cathinones". Drug Test Anal. 16 (12): 1409–1435. doi:10.1002/dta.3662. PMC 11635063. PMID 38389255.
- ^ Shalabi AR, Walther D, Baumann MH, Glennon RA (June 2017). "Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release". ACS Chem Neurosci. 8 (6): 1397–1403. doi:10.1021/acschemneuro.7b00055. PMC 7261150. PMID 28220701.
- ^ Shalabi, Abdelrahman R. (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. VCU Scholars Compass (Thesis). doi:10.25772/M4E1-3549. Retrieved 24 November 2024.
- Glennon RA (2014). "Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention". Adv Pharmacol. 69: 581–620. doi:10.1016/B978-0-12-420118-7.00015-9. PMC 4471862. PMID 24484988.
Bupropion, the N-tert-butyl analog of 3-chlorocathinone, is a clinically employed antidepressant.
Phenethylamines | |
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Phenethylamines |
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Amphetamines |
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Phentermines |
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Cathinones |
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Phenylisobutylamines | |
Phenylalkylpyrrolidines | |
Catecholamines (and close relatives) |
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Miscellaneous |
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