meta-Chlorophenylpiperazine

*meta*-Chlorophenylpiperazine
Clinical data
Routes of; administration	Oral, intranasal, rectal
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); DE: Anlage II (Authorized trade only, not prescriptible);
Pharmacokinetic data
Metabolism	Liver (CYP2D6)
Elimination half-life	4–14 hours
Excretion	Urine
Identifiers
	IUPAC name 1-(3-chlorophenyl)piperazine;
CAS Number	6640-24-0 ;
PubChem CID	1355;
IUPHAR/BPS	142;
ChemSpider	1314 ;
UNII	REY0CNO998;
KEGG	C11738;
ChEBI	CHEBI:10588 ;
ChEMBL	ChEMBL478 ;
CompTox Dashboard (EPA)	DTXSID9045138 ;
ECHA InfoCard	100.026.959
Chemical and physical data
Formula	C10H13ClN2
Molar mass	196.68 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cc(ccc1)N2CCNCC2;
	InChI InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2 ; Key:VHFVKMTVMIZMIK-UHFFFAOYSA-N ;
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meta-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s. It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as "ecstasy" in Europe and the United States.

Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users. It lacks any reinforcing effects, but has "psychostimulant, anxiety-provoking, and hallucinogenic effects." It is also known to produce dysphoric, depressive, and anxiogenic effects in rodents and humans, and can induce panic attacks in individuals susceptible to them. It also worsens obsessive–compulsive symptoms in people with the disorder.

mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications. It has potent anorectic effects and has encouraged the development of selective 5-HT_2C receptor agonists for the treatment of obesity as well.

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