1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is a

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. D ...

of the

piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...

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 Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seven ...

at its 4-position. It was first described in 1994 in a patent disclosing a series of

compounds as

sigma receptor Sigma receptors (σ-receptors) are protein cell surface receptors that bind ligands such as 4-PPBP (4-phenyl-1-(4-phenylbutyl) piperidine), SA 4503 (cutamesine), ditolylguanidine, dimethyltryptamine, and siramesine. There are two subtypes, ...

ligands. Later, it was discovered to be a highly potent

dopamine reuptake inhibitor A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dop ...

Pharmacology

3C-PEP is one of the most potent

dopamine transporter The dopamine transporter (also dopamine active transporter, DAT, SLC6A3) is a membrane-spanning protein that pumps the neurotransmitter dopamine out of the synaptic cleft back into cytosol. In the cytosol, other transporters sequester the dop ...

(DAT) ligand reported to date. It is highly selective for the

(dissociation constant K = 0.04 nM) with relatively low

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Par ...

for the closely related

norepinephrine transporter The norepinephrine transporter (NET), also known as noradrenaline transporter (NAT), is a protein that in humans is encoded by the solute carrier family 6 member 2 (SLC6A2) gene. NET is a monoamine transporter and is responsible for the sodium- ...

(NET, K = 1107 nM ) and the

serotonin transporter The serotonin transporter (SERT or 5-HTT) also known as the sodium-dependent serotonin transporter and solute carrier family 6 member 4 is a protein that in humans is encoded by the SLC6A4 gene. SERT is a type of monoamine transporter protein tha ...

(SERT, K = 802 nM). In addition, the compound has lower (or no) affinity for

D2-like receptor The D2-like receptors are a subfamily of dopamine receptors that bind the endogenous neurotransmitter dopamine. The D2-like subfamily consists of three G-protein coupled receptors that are coupled to Gi/Go and mediate inhibitory neurotransmission ...

(K = 327 nM), serotonin

5-HT2 receptor The 5-HT2 receptors are a subfamily of 5-HT receptors that bind the endogenous neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). The 5-HT2 subfamily consists of three G protein-coupled receptors (GPCRs) which are coupled to Gq/G11 and media ...

(K = 53 nM),

opioid receptor Opioid receptors are a group of inhibitory G protein-coupled receptors with opioids as ligands. The endogenous opioids are dynorphins, enkephalins, endorphins, endomorphins and nociceptin. The opioid receptors are ~40% identical to somatostatin ...

(K>10000 nM), and the PCP/ NMDA receptor (K>10000 nM). With a DAT dissociation constant K of 0.04 nM, 3C-PEP is one of the most potent dopamine transporter ligand described to date in the literature. In comparison,

cocaine Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Ameri ...

which is a prototypical DAT ligand and reuptake inhibitor has a dissociation constant K of 435 nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology ...

''.

Legal status

United States

3C-PEP is not scheduled at the federal level in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

Canada

3C-PEP is not scheduled under the

Controlled Drugs and Substances Act The ''Controlled Drugs and Substances Act'' (french: Loi réglementant certaines drogues et autres substances) (the ''Act'') is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeal ...

References

{{DEFAULTSORT:Chlorophenyl)-4-(2-phenylethyl)piperazine, 1-(3- Chlorobenzenes Stimulants Meta-Chlorophenylpiperazines Piperazines Dopamine reuptake inhibitors

Pharmacology

Legal status

United States

Canada

See also

References