1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine

1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine is a drug developed by a team led by Alan Kozikowski, which acts as a potent dopamine reuptake inhibitor, and was developed as a potential therapeutic agent for the treatment of cocaine addiction.[1] As with related compounds such as nocaine, it is a structurally simplified derivative of related phenyltropane compounds.[2] Its activity at the serotonin and noradrenaline transporters has not been published, though most related 4-phenylpiperidine derivatives are relatively selective for inhibiting dopamine reuptake over the other monoamine neurotransmitters. While several of its isomers are active, the (3S,4S)-enantiomer is by far the most potent.[3][4] The rearranged structural isomer 2-[1-(4-chlorophenyl)butyl]piperidine is also a potent inhibitor of dopamine reuptake.[5]

2-[1-(4-chlorophenyl)butyl]piperidine
1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine
Identifiers
IUPAC name
  • (3S,4S)-4-(4-Chloro-phenyl)-1-methyl-3-propyl-piperidine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H22ClN
Molar mass251.80 g·mol−1
3D model (JSmol)
SMILES
  • CCC[C@@H]1CN(CC[C@@H]1C2=CC=C(C=C2)Cl)C
InChI
  • InChI=1S/C15H22ClN/c1-3-4-13-11-17(2)10-9-15(13)12-5-7-14(16)8-6-12/h5-8,13,15H,3-4,9-11H2,1-2H3/t13-,15-/m1/s1
  • Key:MWGRXFWGMDSMNI-UKRRQHHQSA-N

See also

References
  1. US 6180648, Kozikowski AP, Araldi GL, "Analogs of cocaine", issued 2001-01-30, assigned to George Town University
  2. Kozikowski AP, Araldi GL, Prakash KR, Zhang M, Johnson KM (December 1998). "Synthesis and biological properties of new 2beta-alkyl- and 2beta-aryl-3-(substituted phenyl)tropane derivatives: stereochemical effect of C-3 on affinity and selectivity for neuronal dopamine and serotonin transporters". Journal of Medicinal Chemistry. 41 (25): 4973–82. doi:10.1021/jm9802564. PMID 9836615.
  3. Kozikowski AP, Araldi GL, Boja J, Meil WM, Johnson KM, Flippen-Anderson JL, George C, Saiah E (May 1998). "Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton". Journal of Medicinal Chemistry. 41 (11): 1962–9. doi:10.1021/jm980028+. PMID 9599245.
  4. US 6440996, Kozikowski AP, Araldi GL, Tamiz AP, "Monomeric and dimeric heterocycles, and therapeutic uses thereof", issued 2002-08-27, assigned to Georgetown University
  5. Froimowitz M, Gu Y, Dakin LA, Nagafuji PM, Kelley CJ, Parrish D, Deschamps JR, Janowsky A (January 2007). "Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter". Journal of Medicinal Chemistry. 50 (2): 219–32. doi:10.1021/jm0608614. PMID 17228864.


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