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meta-Chlorophenylpiperazine
Systematic (IUPAC) name
1-(3-Chlorophenyl)piperazine
Identifiers
CAS number 51639-49-7
ATC code  ?
PubChem 1355
ChemSpider 1314
Chemical data
Formula C 10H13ClN2  
Mol. mass 196.676 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism hepatic
Half life  ?
Excretion renal
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes oral, nasal, rectal
 X mark.svgN(what is this?)  (verify)
Tablets containing mCPP confiscated by the DEA in Vernon Hills, Illinois

meta-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the piperazine chemical class. It acts as a nonselective serotonin receptor agonist. Since 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.

mCPP is known to induce headaches in humans,[1][2] and has been used for testing potential anti-migraine medications.[3] 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.

Contents

Legal status

  • In the Netherlands: Legal
  • In the United States: Legal
  • In Denmark: Illegal[4]
  • In Germany: Illegal
  • In Sweden: Legal
  • In Norway: Legal
  • In Brazil: Illegal[5]
  • In the United Kingdom: Legal
  • In Belgium: Illegal [6]

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 18 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 remained until October 2008, at which point they became completely illegal.[7]

Use in research

mCPP has been used to study the effects of the 5-HT2C receptor in the basal ganglia.[8] Studies showed that mCPP administration activates neurons in the substantia nigra pars reticula, and fails to do so in the presence of an antagonist.[9]

See also

References

  1. ^ Leone, M; A Attanasio, D Croci, G Filippini, D D'Amico, L Grazzi, A Nespolo, G Bussone (July 12, 2000). "The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study". Neurology 55 (1): 136–9. PMID 10891925.  
  2. ^ 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
  3. ^ 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.
  4. ^ Erowid.org
  5. ^ ANVISA resolution - Portaria SVS/MS 344/98
  6. ^ EMCDDA
  7. ^ Misuse of Drugs (Classification of BZP) Amendment Bill 2008
  8. ^ Esposito E (February 2006). "Serotonin-dopamine interaction as a focus of novel antidepressant drugs". Curr Drug Targets 7 (2): 177–85. doi:10.2174/138945006775515455. PMID 16475959.  
  9. ^ Di Giovanni et al., 2001







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