| 词条 | 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine |
| 释义 |
| IUPAC_name = 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine | image = 3C-PEP_structure.png | width = 220 | tradename = | routes_of_administration = | legal_status = | CAS_number_Ref = | CAS_number = 136534-45-7 | ATC_suffix = | PubChem = 2845469 | ChemSpiderID = 2121938 | C=18 | H=21 | Cl=1 | N=2 | molecular_weight = 300.8 g/mol | smiles = ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3 | StdInChI = 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 | StdInChIKey = 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] Pharmacology3C-PEP is one of the most potent dopamine transporter (DAT) ligand reported to date. It is highly selective for the dopamine transporter (dissociation constant K{{sub|i}} = 0.04 nM) with relatively low affinity for the closely related norepinephrine transporter (NET, K{{sub|i}} = 1107 nM ) and the serotonin transporter (SERT, K{{sub|i}} = 802 nM). In addition, the compound has little or no affinity for D2-like receptor (K{{sub|i}} = 327 nM), serotonin 5-HT2 receptor (K{{sub|i}} = 53 nM), opioid receptor (K{{sub|i}}>10000 nM), and the PCP/NMDA receptor (K{{sub|i}}>10000 nM).[2] With a DAT dissociation constant K{{sub|i}} 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 K{{sub|i}} of 435 nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor in vitro.[2] Legal statusUnited States3C-PEP is not scheduled at the federal level in the United States,[3] Canada3C-PEP is not scheduled under the Controlled Drugs and Substances Act. See also
References1. ^{{cite web|last1 = Glennon|first1 = Richard A|title = Sigma receptor ligands and the use thereof|url = http://www.google.com/patents/US6057371}} {{Stimulants}}{{Dopaminergics}}{{DEFAULTSORT:Chlorophenyl)-4-(2-phenylethyl)piperazine, 1-(3-}}2. ^1 2 {{cite journal|vauthors=Motel WC, Healy JR, Viard E, Pouw B, Martin KE, Matsumoto RR, Coop A|title = Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands|journal = Bioorg Med Chem Lett|year = 2013|volume = 23|issue = 24|pages = 6020–6922|pmid = 24211020|pmc = 3919026|doi = 10.1016/j.bmcl.2013.09.038}} 3. ^21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. 4 : Chloroarenes|Stimulants|Piperazines|Dopamine reuptake inhibitors |
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