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]

Other names3-CC; Norclophedrone; 3Cl-C; 3Cl-Cathinone; 3-Chloro-β-ketoamphetamine

Drug classStimulant; Serotonin–norepinephrine–dopamine releasing agent

CAS Number

• 119802-69-6 ^Y

PubChem CID

• 22031823

Quick facts Clinical data, Other names ...

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 Y
PubChem CID	22031823
ChemSpider	10769205
UNII	WE6T7CGT56
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

Close

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]