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

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1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
Identifiers
  • 1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine
Chemical and physical data
FormulaC18H21ClN2
Molar mass300.8 g/mol g·mol−1
3D model (JSmol)
  • ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3
  • 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 psychoactive recreational drug of the piperazine class. It is presumably a potent psychostimulant with reportedly aphrodisiac properties.[original research?] 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 by researchers at the University of Maryland to be a highly potent dopamine reuptake inhibitor.[2] Rather serendipitously, since the investigators were looking for compounds that bind to the Sigma receptor as Sigma ligands have been proposed as potential treatment of psychostimulant abuse including cocaine and methamphetamine abuse.

Pharmacology

3C-PEP is one of the most potent dopamine transporter (DAT) ligand reported to date. It is highly selective for the dopamine transporter (DAT dissociation constant Ki = 0.04nM with relatively low affinity for the closely related Norepinephrine transporter NET (Ki = 1107nM ) and the Serotonine Transporter SERT (Ki = 802 nm). In addition, the compound has little or no affinity for D2-like receptor (Ki = 327nM), Serotonin 5-HT2 receptor, (Ki = 53nM) Opioid receptor (Ki>10000nM) and the PCP/NMDA receptor (Ki>10000nM).[original research?]

With a DAT dissociation constant Ki of 0.04nM, 3C-PEP is 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. Similarly to related 1-4 disubstiuted piperazines such as Etoperidone, Nefazodone or Trazodone, 3C-PEP presumably might be expected to be metabolized to mCPP.[original research?]

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.

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 Letters. 23 (24): 6020–6922. doi:10.1016/j.bmcl.2013.09.038. PMC 3919026. PMID 24211020.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.


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