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| Formula | C18H21ClN2 |
| Molar mass | 300.83 g·mol−1 |
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1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is adesigner drug of thepiperazine class of chemical substances. 3C-PEP is related tometa-cholorophenylpiperazine (mCPP) andphenethylamine which can be thought of as mCPP having a phenylethyl group attached to thenitrogen atom at its 4-position. It was first described in 1994 in a patent disclosing a series ofpiperazine compounds assigma receptor ligands.[1] Later, it was discovered to be a highly potentdopamine reuptake inhibitor.[2]
3C-PEP is one of the most potentdopamine transporter (DAT) ligands reported to date. It is highlyselective for thedopamine transporter (dissociation constant Ki = 0.04 nM) with relatively lowaffinity for the closely relatednorepinephrine transporter (NET, Ki = 1107 nM ) and theserotonin transporter (SERT, Ki = 802 nM). In addition, the compound has lower (or no) affinity for the PCP/NMDA receptor (Ki > 10000 nM),[2]D2-like receptors (Ki = 327 nM),serotonin5-HT2 receptors (Ki = 53 nM), andopioid receptors (Ki > 10000 nM).
With a DAT dissociation constant Ki of 0.04 nM, 3C-PEP is one of the most potent dopamine transporter ligands 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 inhibitorin vitro.[2]
3C-PEP is not scheduled at the federal level in theUnited States,[3]
3C-PEP is not scheduled under theControlled Drugs and Substances Act.
