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

Chemical compound 1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine (3S,4S)-4-(4-Chloro-phenyl)-1-methyl-3-propyl-piperidine 1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine_structure.png skin-invert-image correct CAS 214335-23-6 (3S,4S enantiomer) 1956381-81-9 (racemate) 9837874 correct FDA PJ74S72YHZ 8013594 109097 15 22 1 1 CCC[C@@H]1CN(CC[C@@H]1C2=CC=C(C=C2)Cl)C 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 MWGRXFWGMDSMNI-UKRRQHHQSA-N 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. US 6180648 Kozikowski AP, Araldi GL George Town University 2001-01-30 Analogs of cocaine As with related compounds such as nocaine, it is a structurally simplified derivative of related phenyltropane compounds. Kozikowski AP, Araldi GL, Prakash KR, Zhang M, Johnson KM 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 December 1998 9836615 10.1021/jm9802564 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. Kozikowski AP, Araldi GL, Boja J, Meil WM, Johnson KM, Flippen-Anderson JL, George C, Saiah E 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 May 1998 9599245 10.1021/jm980028+ Kozikowski AP, Araldi GL, Tamiz AP Georgetown University Monomeric and dimeric heterocycles, and therapeutic uses thereof US 6440996 2002-08-27 The rearranged structural isomer 2-[1-(4-chlorophenyl)butyl]piperidine is also a potent inhibitor of dopamine reuptake. Froimowitz M, Gu Y, Dakin LA, Nagafuji PM, Kelley CJ, Parrish D, Deschamps JR, Janowsky A Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter Journal of Medicinal Chemistry 50 2 219–32 January 2007 17228864 10.1021/jm0608614 class=skin-invert-image|200px|thumb|left|2-[1-(4-chlorophenyl)butyl]piperidine16102751 led to CTDP-32476 See also 4-Fluoropethidine Allylprodine JZ-IV-10 N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate WY-46824 References Category:Dopamine reuptake inhibitors Category:4-Phenylpiperidines Category:4-Chlorophenyl compounds