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

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[1] disclosing a series of piperazine compounds as sigma receptor ligands. Later, it was discovered to be a highly potent dopamine reuptake inhibitor.[2]

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
Identifiers
IUPAC name
  • 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.83 g·mol−1
3D model (JSmol)
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

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 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 lower (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).[2]

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.[2]

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.

See also

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