1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
Identifiers
	IUPAC name 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine;
CAS Number	136534-45-7 ;
PubChem CID	2845469;
ChemSpider	2121938;
UNII	3LEH2E7AEU;
CompTox Dashboard (EPA)	DTXSID501032720 ;
Chemical and physical data
Formula	C18H21ClN2
Molar mass	300.83 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3;
	InChI InChI=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; Key: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-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.^[1] Later, it was discovered to be a highly potent dopamine reuptake inhibitor.^[2]

Pharmacology

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 K_i = 0.04 nM) with relatively low affinity for the closely related norepinephrine transporter (NET, K_i = 1107 nM ) and the serotonin transporter (SERT, K_i = 802 nM). In addition, the compound has lower (or no) affinity for D2-like receptor (K_i = 327 nM), serotonin 5-HT2 receptor (K_i = 53 nM), opioid receptor (K_i > 10000 nM), and the PCP/NMDA receptor (K_i > 10000 nM).^[2]

With a DAT dissociation constant K_i 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 K_i of 435 nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor in vitro.^[2]

Legal status

United States

3C-PEP is not scheduled at the federal level in the United States,^[3]

Canada

3C-PEP is not scheduled under the Controlled Drugs and Substances Act.

References

^ Glennon, Richard A. "Sigma receptor ligands and the use thereof".
^ ^a ^b ^c 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." Archived from the original on 2009-08-27. Retrieved 2015-09-15.

[1] Glennon, Richard A. "Sigma receptor ligands and the use thereof".

[pmid10721502-2] 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.

[PART_1308_—_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-3] "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2015-09-15.

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