3-Chloro-N-cyclopropylcathinone

3-Chloro-N-cyclopropylcathinone (3Cl-CpC; code names PAL-433, RTI-6037-39) is a stimulant and hybrid monoamine releasing agent and monoamine reuptake inhibitor of the cathinone family related to bupropion (3-chloro-N-tert-butylcathinone).^[1][2][3]

Other names3Cl-CpC; 3′-Chloro-2-(cyclopropylamino)-propanophenone; 2-(N-Cyclopropylamino)-3-chloropropiophenone; PAL-433; PAL433; RTI-6037-39

Drug classStimulant; Serotonin releasing agent; Serotonin–norepinephrine–dopamine reuptake inhibitor

CAS Number

• 1193779-70-2

PubChem CID

• 44543271

Quick facts Clinical data, Other names ...

3-Chloro-N-cyclopropylcathinone

Clinical data
Other names	3Cl-CpC; 3′-Chloro-2-(cyclopropylamino)-propanophenone; 2-(N-Cyclopropylamino)-3-chloropropiophenone; PAL-433; PAL433; RTI-6037-39
Drug class	Stimulant; Serotonin releasing agent; Serotonin–norepinephrine–dopamine reuptake inhibitor
Identifiers
IUPAC name 1-(3-chlorophenyl)-2-(cyclopropylamino)propan-1-one
CAS Number	1193779-70-2
PubChem CID	44543271
ChemSpider	24631232
ChEMBL	ChEMBL569700
Chemical and physical data
Formula	C12H14ClNO
Molar mass	223.70 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC(=CC=C1)Cl)NC2CC2
InChI InChI=1S/C12H14ClNO/c1-8(14-11-5-6-11)12(15)9-3-2-4-10(13)7-9/h2-4,7-8,11,14H,5-6H2,1H3 Key:YKOZIWZLLJVPPD-UHFFFAOYSA-N

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It acts specifically as a dual serotonin releasing agent (SRA) and serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI).^[1][2][3] Its EC₅₀Tooltip half-maximal effective concentration for induction of serotonin release is 1,328 nM, whereas its IC₅₀Tooltip half-maximal inhibitory concentration values for monoamine reuptake inhibition are 265 to 533 nM for dopamine, 2,150 nM for norepinephrine, and 3,180 nM for serotonin.^[1][2][3] The drug produces psychostimulant-like effects in animals, with a slow onset of action and a long duration of action.^[1][3] The activities of the individual enantiomers of 3Cl-CpC, (−)-3Cl-CpC (PAL-1122) and (+)-3Cl-CpC (PAL-1123), have also been reported.^[2]

3Cl-CpC was first described in the scientific literature by 2009.^[1][2][3] It was being investigated by the National Institute on Drug Abuse (NIDA) as a potential treatment of stimulant dependence, including cocaine dependence specifically.^[1][2][3]