Chemistry:1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine
 | |
| Identifiers | |
|---|---|
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| Chemical and physical data | |
| Formula | C18H21ClN2 |
| Molar mass | 300.83 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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 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]
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
- Substituted piperazine
- Etoperidone, nefazodone, and trazodone (structurally related drugs which may also produce mCPP as a metabolite)
- CM156
- Diphenpipenol
- MT-45
References
- ↑ Glennon, Richard A. "Sigma receptor ligands and the use thereof". http://www.google.com/patents/US6057371.
- ↑ 2.0 2.1 2.2 "Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands". Bioorg Med Chem Lett 23 (24): 6020–6922. 2013. doi:10.1016/j.bmcl.2013.09.038. PMID 24211020.
- ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm.
 |  |
