3-Chloro-N-cyclopropylcathinone

{{DISPLAYTITLE:3-Chloro-N-cyclopropylcathinone}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| drug_name = 3-Chloro-N-cyclopropylcathinone

| image = 3-Chloro-N-cyclopropylcathinone.svg

| width =

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class = Stimulant; Serotonin releasing agent; Serotonin–norepinephrine–dopamine reuptake inhibitor

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number = 1193779-70-2

| CAS_supplemental =

| PubChem = 44543271

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 24631232

| UNII =

| KEGG =

| ChEBI =

| ChEMBL = 569700

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = 3Cl-CpC; 3′-Chloro-2-(cyclopropylamino)-propanophenone; 2-(N-Cyclopropylamino)-3-chloropropiophenone; PAL-433; PAL433; RTI-6037-39

| IUPAC_name = 1-(3-chlorophenyl)-2-(cyclopropylamino)propan-1-one

| C=12 | H=14 | Cl=1 | N=1 | O=1

| SMILES = CC(C(=O)C1=CC(=CC=C1)Cl)NC2CC2

| StdInChI = 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

| StdInChIKey = YKOZIWZLLJVPPD-UHFFFAOYSA-N

}}

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).{{cite journal | vauthors = Carroll FI, Blough BE, Abraham P, Mills AC, Holleman JA, Wolckenhauer SA, Decker AM, Landavazo A, McElroy KT, Navarro HA, Gatch MB, Forster MJ | title = Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction | journal = Journal of Medicinal Chemistry | volume = 52 | issue = 21 | pages = 6768–6781 | date = November 2009 | pmid = 19821577 | doi = 10.1021/jm901189z }}{{cite journal | vauthors = Blough BE, Landavazo A, Partilla JS, Baumann MH, Decker AM, Page KM, Rothman RB | title = Hybrid dopamine uptake blocker-serotonin releaser ligands: a new twist on transporter-focused therapeutics | journal = ACS Medicinal Chemistry Letters | volume = 5 | issue = 6 | pages = 623–627 | date = June 2014 | pmid = 24944732 | pmc = 4060932 | doi = 10.1021/ml500113s }}{{cite book | vauthors = Carroll FI, Blough BE, Mascarella SW, Navarro HA, Lukas RJ, Damaj MI | title = Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse | chapter = Bupropion and bupropion analogs as treatments for CNS disorders | series = Advances in Pharmacology | volume = 69 | pages = 177–216 | date = 2014 | pmid = 24484978 | doi = 10.1016/B978-0-12-420118-7.00005-6 | isbn = 978-0-12-420118-7 }}

It acts specifically as a dual serotonin releasing agent (SRA) and serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI). Its {{Abbrlink|EC₅₀|half-maximal effective concentration}} for induction of serotonin release is 1,328{{nbsp}}nM, whereas its {{Abbrlink|IC₅₀|half-maximal inhibitory concentration}} values for monoamine reuptake inhibition are 265 to 533{{nbsp}}nM for dopamine, 2,150{{nbsp}}nM for norepinephrine, and 3,180{{nbsp}}nM for serotonin. The drug produces psychostimulant-like effects in animals, with a slow onset of action and a long duration of action. The activities of the individual enantiomers of 3Cl-CpC, (–)-3Cl-CpC (PAL-1122) and (+)-3Cl-CpC (PAL-1123), have also been reported.

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