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

Chemical compound September 2015 3C-PEP 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine 3C-PEP structure.svg skin-invert-image 250px correct CAS 147429-37-6 correct FDA 3LEH2E7AEU 2845469 2121938 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine 18 21 1 2 ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3 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 NKMGWZZAFWDLFG-UHFFFAOYSA-N 3C-PEP, also known as 1-(3-chlorophenyl)-4-(2-phenylethyl)piperazine, is a designer drug of the piperazine class of chemical substances. 3C-PEP is related to meta-cholorophenylpiperazine (mCPP) and phenethylamine which 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. Glennon Richard A Sigma receptor ligands and the use thereof https://patents.google.com/patent/US6057371 Later, it was discovered to be a highly potent dopamine reuptake inhibitor.Motel WC, Healy JR, Viard E, Pouw B, Martin KE, Matsumoto RR, Coop A Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands Bioorg Med Chem Lett 2013 23 24 6020–6922 24211020 3919026 10.1016/j.bmcl.2013.09.038 Pharmacology 3C-PEP is one of the most potent dopamine transporter (DAT) ligands 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 the PCP/NMDA receptor (Ki > 10000 nM), D2-like receptors (Ki = 327 nM), serotonin 5-HT2 receptors (Ki = 53 nM), and opioid receptors (Ki > 10000 nM). With a DAT dissociation constant Ki of 0.04 nM, 3C-PEP is one of the most potent dopamine transporter ligands 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. Legal status United States 3C-PEP is not scheduled at the federal level in the United States,http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. 2015-09-15 2009-08-27 https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm dead 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 Category:3-Chlorophenyl compounds Category:Dopamine reuptake inhibitors Category:1-Phenylpiperazines Category:Stimulants