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|Chemical and physical data|
|Molar mass||300.8 g/mol g·mol−1|
|3D model (JSmol)|
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-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. Later, it was discovered to be a highly potent dopamine reuptake inhibitor.
3C-PEP is one of the most potent dopamine transporter (DAT) ligand reported to date. It is highly selective for the dopamine transporter (dissociation constant Ki = 0.04 nM) with relatively low affinity for the closely related norepinephrine transporter (NET, Ki = 1107 nM ) and the serotonin transporter (SERT, Ki = 802 nM). In addition, the compound has little or no affinity for D2-like receptor (Ki = 327 nM), serotonin 5-HT2 receptor (Ki = 53 nM), opioid receptor (Ki>10000 nM), and the PCP/NMDA receptor (Ki>10000 nM).
With a DAT dissociation constant Ki of 0.04 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 Ki of 435 nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor in vitro.
3C-PEP is not scheduled under the Controlled Drugs and Substances Act.
- Substituted piperazine
- Etoperidone, nefazodone, and trazodone (structurally related drugs which may also produce mCPP as a metabolite)
- Glennon, Richard A. "Sigma receptor ligands and the use thereof".
- Motel WC, Healy JR, Viard E, Pouw B, Martin KE, Matsumoto RR, Coop A (2013). "Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands". Bioorg Med Chem Lett. 23 (24): 6020–6922. doi:10.1016/j.bmcl.2013.09.038. PMC 3919026. PMID 24211020.
- 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.