|Systematic (IUPAC) name|
|Mol. mass||196.676 g/mol|
1-(3-Chlorophenyl)piperazine (or meta-chlorophenylpiperazine, mCPP) is a piperazine-based 5-HT receptor agonist that has been used as a challenge drug in MDMA research. In the mid-2000s, it has shown up in legal alternatives to illegal stimulants in New Zealand, and pills sold as ecstasy in Europe and the United States.
mCPP is known to induce headaches in humans, and has been used for testing potential anti-migraine medications. Up to 10% of people who take mCPP will develop a migraine headache, and 90% of individuals who commonly suffer from migraines will have an attack induced by mCPP. This has tended to limit the use of mCPP as a recreational drug.
In the US: unscheduled
In New Zealand: unscheduled
In Denmark: Banned 
In Germany: Banned
- Benzylpiperazine (BZP)
- Trifluoromethylphenylpiperazine (TFMPP)
- Trazodone -- metabolises to mCPP in vivo
- Leone, M (July 12 2000). "The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study". Neurology. 55 (1): 136–9. PMID 10891925.
- Martin RS & Martin GR. Investigations into migraine pathogenesis: time course for effects of m-CPP, BW723C86 or glyceryl trinitrate on appearance of Fos-like immunoreactivity in rat trigeminal nucleus caudalis (TNC). Cephalalgia 2001; 21:46–52. London. ISSN 0333-10245
- Petkov VD, Belcheva S, Konstantinova E. Anxiolytic effects of dotarizine, a possible antimigraine drug. Methods Find Exp Clin Pharmacol. 1995 Dec;17(10):659-68.