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
PubChem CID
ChemSpider
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

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]

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 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).[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. 1 2 3 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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