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

{{Short description|Chemical compound}}

{{DISPLAYTITLE:1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine}}

{{Drugbox

| drug_name = 1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine

| IUPAC_name = (3S,4S)-4-(4-Chloro-phenyl)-1-methyl-3-propyl-piperidine

| image = 1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine_structure.png

| image_class = skin-invert-image

| tradename =

| CAS_number = 214335-23-6

| CAS_supplemental = (3S,4S enantiomer)
1956381-81-9 (racemate)

| ATC_prefix =

| ATC_suffix =

| PubChem = 9837874

| ChemSpiderID = 8013594

| ChEMBL = 109097

| C=15 | H=22 | Cl=1 | N=1

| smiles = CCC[C@@H]1CN(CC[C@@H]1C2=CC=C(C=C2)Cl)C

| StdInChI = 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

| StdInChIKey = 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.{{cite patent | country = US | number = 6180648 | inventor = Kozikowski AP, Araldi GL | assign = George Town University | gdate = 2001-01-30 | title = Analogs of cocaine }} As with related compounds such as nocaine, it is a structurally simplified derivative of related phenyltropane compounds.{{cite journal | vauthors = Kozikowski AP, Araldi GL, Prakash KR, Zhang M, Johnson KM | title = 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 = Journal of Medicinal Chemistry | volume = 41 | issue = 25 | pages = 4973–82 | date = December 1998 | pmid = 9836615 | doi = 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.{{cite journal | vauthors = Kozikowski AP, Araldi GL, Boja J, Meil WM, Johnson KM, Flippen-Anderson JL, George C, Saiah E | title = Chemistry and pharmacology of the piperidine-based analogues of cocaine. Identification of potent DAT inhibitors lacking the tropane skeleton | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 11 | pages = 1962–9 | date = May 1998 | pmid = 9599245 | doi = 10.1021/jm980028+ | citeseerx = 10.1.1.512.7158 }}{{cite patent | inventor = Kozikowski AP, Araldi GL, Tamiz AP | assign1 = Georgetown University | title = Monomeric and dimeric heterocycles, and therapeutic uses thereof | country = US | number = 6440996 | gdate = 2002-08-27 }} The rearranged structural isomer 2-[1-(4-chlorophenyl)butyl]piperidine is also a potent inhibitor of dopamine reuptake.{{cite journal | vauthors = Froimowitz M, Gu Y, Dakin LA, Nagafuji PM, Kelley CJ, Parrish D, Deschamps JR, Janowsky A | title = Slow-onset, long-duration, alkyl analogues of methylphenidate with enhanced selectivity for the dopamine transporter | journal = Journal of Medicinal Chemistry | volume = 50 | issue = 2 | pages = 219–32 | date = January 2007 | pmid = 17228864 | doi = 10.1021/jm0608614 }}

:Image:2-(1-(4-chlorophenyl)butyl)piperidine_structure.png{{Clear-left}}