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-Chlorocathinone

Clinical data
Other names	3-CC; Norclophedrone; 3Cl-C; 3Cl-Cathinone; 3-Chloro-β-ketoamphetamine
Drug class	Stimulant; Serotonin–norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 2-amino-1-(3-chlorophenyl)propan-1-one
CAS Number	119802-69-6
PubChem CID	22031823
ChemSpider	10769205
CompTox Dashboard (EPA)	DTXSID80621813
Chemical and physical data
Formula	C9H10ClNO
Molar mass	183.64 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC(=CC=C1)Cl)N
InChI InChI=1S/C9H10ClNO/c1-6(11)9(12)7-3-2-4-8(10)5-7/h2-6H,11H2,1H3 Key:RDWWHMAISJGIDU-UHFFFAOYSA-N

3-CC is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[3][4] 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.^[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]

References

1. Mazzoni I, Rabin O (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.
2. 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.
3. 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.
4. 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.
5. 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. Bupropion, the N-tert-butyl analog of 3-chlorocathinone, is a clinically employed antidepressant.