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((Short description|Chemical compound))
((more citations needed|date=September 2015))
((Drugbox
| IUPAC_name    = 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
| image         = 3C-PEP_structure.png
| width         = 220


<!--Clinical data-->
| tradename                =
| routes_of_administration =
| legal_status =

<!--Identifiers-->
| CAS_number_Ref = ((cascite|correct|CAS))
| CAS_number = 136534-45-7
| UNII_Ref = ((fdacite|correct|FDA))
| UNII = 3LEH2E7AEU
| ATC_suffix     = 
| PubChem        = 2845469
| ChemSpiderID = 2121938

<!--Chemical data-->
| C=18 | H=21 | Cl=1 | N=2
| smiles = ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3
| StdInChI = 1S/C18H21ClN2/c19-17-7-4-8-18(15-17)21-13-11-20(12-14-21)10-9-16-5-2-1-3-6-16/h1-8,15H,9-14H2
| StdInChIKey = NKMGWZZAFWDLFG-UHFFFAOYSA-N
))

'''1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine''' ('''3C-PEP''') is a [[designer drug]] of the [[piperazine]] class of chemical substances. 3C-PEP is related to [[Meta-Chlorophenylpiperazine|''meta''-cholorophenylpiperazine]] (mCPP) and [[phenethylamine]] that can be thought of as mCPP having a phenylethyl group attached to the [[nitrogen atom]] at its 4-position. It was first described in 1994 in a patent disclosing a series of [[piperazine]] compounds as [[sigma receptor]] ligands.<ref>((cite web|last1 = Glennon|first1 = Richard A|title = Sigma receptor ligands and the use thereof|url = http://www.google.com/patents/US6057371))</ref>   Later, it was discovered to be a highly potent [[dopamine reuptake inhibitor]].<ref name="pmid10721502">((cite journal|vauthors=Motel WC, Healy JR, Viard E, Pouw B, Martin KE, Matsumoto RR, Coop A|title = Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands|journal = Bioorg Med Chem Lett|year = 2013|volume = 23|issue = 24|pages = 6020–6922|pmid = 24211020|pmc = 3919026|doi = 10.1016/j.bmcl.2013.09.038))</ref>

== Pharmacology ==
3C-PEP is one of the most potent [[dopamine transporter]] (DAT) ligand reported to date. It is highly [[Binding selectivity|selective]] for the [[dopamine transporter]] (dissociation constant K((sub|i)) = 0.04&nbsp;nM) with relatively low [[affinity (pharmacology)|affinity]] for the closely related [[norepinephrine transporter]] (NET, K((sub|i)) = 1107&nbsp;nM ) and the [[serotonin transporter]] (SERT, K((sub|i)) = 802&nbsp;nM).  In addition, the compound has lower (or no) affinity for [[D2-like receptor]] (K((sub|i)) = 327&nbsp;nM), [[serotonin]] [[5-HT2 receptor]] (K((sub|i)) = 53&nbsp;nM), [[opioid receptor]] (K((sub|i)) > 10000&nbsp;nM), and the PCP/[[NMDA receptor]] (K((sub|i)) > 10000&nbsp;nM).<ref name="pmid10721502"/>

With a DAT dissociation constant K((sub|i)) of 0.04&nbsp;nM, 3C-PEP is one of the most potent dopamine transporter ligand described to date in the literature. In comparison, [[cocaine]] which is a prototypical DAT ligand and reuptake inhibitor has a dissociation constant K((sub|i)) of 435&nbsp;nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor ''[[in vitro]]''.<ref name="pmid10721502"/>

== Legal status ==

=== United States ===
3C-PEP is not scheduled at the federal level in the [[United States]],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">((Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. |access-date=2015-09-15 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead ))</ref>

=== Canada ===
3C-PEP is not scheduled under the [[Controlled Drugs and Substances Act]].

== See also ==
* [[Substituted piperazine]]
* [[Etoperidone]], [[nefazodone]], and [[trazodone]] (structurally related drugs which may also produce mCPP as a metabolite)
* [[CM156]]
* [[Diphenpipenol]]
* [[MT-45]]

== References ==
((Reflist))

((Stimulants))
((Dopaminergics))

((DEFAULTSORT:Chlorophenyl)-4-(2-phenylethyl)piperazine, 1-(3-))
[[Category:Chlorobenzene derivatives]]
[[Category:Stimulants]]
[[Category:Meta-Chlorophenylpiperazines]]
[[Category:Piperazines]]
[[Category:Dopamine reuptake inhibitors]]

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