3-Chloro-N-cyclopropylcathinone

3-Chloro-N-cyclopropylcathinone
Clinical data
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
Identifiers
  • 1-(3-chlorophenyl)-2-(cyclopropylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H14ClNO
Molar mass223.70 g·mol−1
3D model (JSmol)
  • CC(C(=O)C1=CC(=CC=C1)Cl)NC2CC2
  • 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

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]

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]

See also

References

  1. ^ a b c d e f Carroll FI, Blough BE, Abraham P, Mills AC, Holleman JA, Wolckenhauer SA, et al. (November 2009). "Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for cocaine addiction". Journal of Medicinal Chemistry. 52 (21): 6768–6781. doi:10.1021/jm901189z. PMID 19821577.
  2. ^ a b c d e f Blough BE, Landavazo A, Partilla JS, Baumann MH, Decker AM, Page KM, et al. (June 2014). "Hybrid dopamine uptake blocker-serotonin releaser ligands: a new twist on transporter-focused therapeutics". ACS Medicinal Chemistry Letters. 5 (6): 623–627. doi:10.1021/ml500113s. PMC 4060932. PMID 24944732.
  3. ^ a b c d e f Carroll FI, Blough BE, Mascarella SW, Navarro HA, Lukas RJ, Damaj MI (2014). "Bupropion and bupropion analogs as treatments for CNS disorders". Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Advances in Pharmacology. Vol. 69. pp. 177–216. doi:10.1016/B978-0-12-420118-7.00005-6. ISBN 978-0-12-420118-7. PMID 24484978.
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