3C-PEP

CAS: 136534-45-7
Molecular wt: 300.83
Compound class: Phenylpiperazine

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3C-PEP

30 mL liquid at 100 mcg per mL, 3 mg total.
3C-PEP (CAS 136534-45-7) is a phenylpiperazine dopamine transporter ligand with sub-nanomolar DAT affinity and roughly 20,000-fold selectivity over SERT.

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Description

3C-PEP is a phenylpiperazine characterised as a high-affinity, transporter-selective dopamine transporter (DAT) ligand.

It was identified during structure-activity work on sigma-2 selective phenylpiperazines. While substituents were being optimised to reduce activity at other neurotransmitter systems, the 3-chlorophenyl and phenethyl substitution pattern was found to confer preferential affinity for the dopamine transporter rather than the intended sigma-2 selectivity.

Binding constants reported in the primary literature are 0.04 nM at DAT, 53 nM at 5-HT₂, 327 nM at D₂-like receptors, 802 nM at SERT and 1,107 nM at NET. That is approximately 20,000-fold selectivity for DAT over SERT and 27,000-fold over NET. Binding at the PCP/NMDA site and at opioid receptors was not detected within the concentration range assayed.

Published characterisation consists of in vitro binding data. No pharmacokinetic, metabolic or in vivo characterisation has been reported, and transporter conformational preference has not been determined for this compound — DAT ligands of comparable affinity differ in the conformational state they stabilise, and that is not inferable from affinity data alone.

Supplied as an analytical reference material for transporter pharmacology. Identity may be matched against CAS 136534-45-7 and InChIKey NKMGWZZAFWDLFG-UHFFFAOYSA-N. Identity and purity are confirmed by third-party COA, and per-lot analytical documentation is published to the COA archive.

Motel WC, Healy JR, Viard E, Pouw B, Martin K, Matsumoto RR, Coop A. Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands. Bioorganic & Medicinal Chemistry Letters. 2013;23(24):6920–6922. doi:10.1016/j.bmcl.2013.09.038

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