1-(3-Chlorophenyl)piperazine

Drugbox
IUPAC_name = 1-(3-Chlorophenyl)piperazine


width= 140

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CAS_number= 6640-24-0
ATC_prefix=
ATC_suffix=
PubChem= 1355
ChemSpiderID = 1314
DrugBank=
C=10 | H=13 | Cl=1 | N=2
molecular_weight = 196.676 g/mol
bioavailability=
metabolism = hepatic
elimination_half-life=
excretion = renal
pregnancy_category =
legal_status NL = unscheduled
routes_of_administration= oral, nasal, rectal

1-(3-Chlorophenyl)piperazine (or "meta"-chlorophenylpiperazine, mCPP) is a piperazine-based 5-HT receptor agonist. 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,cite journal
last =Leone
first =M
authorlink =
coauthors =A Attanasio, D Croci, G Filippini, D D'Amico, L Grazzi, A Nespolo, G Bussone
title =The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study
journal =Neurology
volume =55
issue =1
pages =136–9
date =July 12 2000
url =
doi =
pmid =10891925
accessdate = ] 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] and has been used for testing potential anti-migraine medications.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. ] 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.

Legal status

*In the Netherlands: unscheduled
*In the US: unscheduled
*In Denmark: Banned [ [http://www.erowid.org/psychoactives/law/countries/denmark/denmark_law_info1.shtml Erowid.org] ]
*In Germany: Banned
*In Sweden: legal

Based on the recommendation of the EACD, the New Zealand government has passed legislation which placed BZP, along with the other piperazine derivatives TFMPP, mCPP, pFPP, MeOPP and MBZP, into Class C of the New Zealand Misuse of Drugs Act 1975. A ban was intended to come into effect in New Zealand on December 18th 2007, but the law change did not go through until the following year, and the sale of BZP and the other listed piperazines became illegal in New Zealand as of 1st of April 2008. An amnesty for possession and usage of these drugs will remain until October 2008, at which point they will become completely illegal. [ [http://www.parliament.nz/en-NZ/PB/Legislation/Bills/d/3/d/00DBHOH_BILL8220_1-Misuse-of-Drugs-Classification-of-BZP-Amendment.htm Misuse of Drugs (Classification of BZP) Amendment Bill 2008] ]

ee also

*Benzylpiperazine (BZP)
*Trifluoromethylphenylpiperazine (TFMPP)
*Etoperidone
*Trazodone -- metabolises to mCPP in vivo

References