|Systematic (IUPAC) name|
|Oral, Nasal, Rectal|
|Biological half-life||2-6 hours|
|CAS Registry Number|
|Molecular mass||196.676 g/mol|
|(what is this?)|
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.12 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.34
Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.3 It lacks any reinforcing effects,5 produces depressive and anxiogenic effects in rodents and humans,67 and can induce panic attacks in individuals susceptible to them.891011 It also worsens obsessive-compulsive symptoms in people with the disorder.121314
mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications.151617 It has potent anorectic effects and has encouraged the development of selective 5-HT2C receptor agonists for the treatment of obesity as well.18192021
Meta-chlorophenylpiperazine is a major metabolite of the psychotropic drugs trazodone and nefazodone, and may be responsible for some of their side-effects, such as headaches and migraines induced many hours after initial consumption.
mCPP possesses significant affinity for the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT3, and 5-HT7 receptors, as well as the SERT.22 It also has some affinity for α1-adrenergic, α2-adrenergic, H1, I1, and NET.2223 It behaves as an agonist at most or all serotonin receptors.222425 mCPP has been shown to act not only as a reuptake inhibitor of serotonin but as a releasing agent as well.26
mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.222728 Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor,71829 whereas its psychedelic effects at high doses are caused by 5-HT2A activation. Other effects of mCPP include nausea, hypoactivity, and penile erection, the latter two the result of increased 5-HT2C activity and the former likely via 5-HT3 stimulation.303132
Binding affinity (Ki [nM]) towards cloned human receptors where data is available
|BDZ receptor||>10000 (HB)|
RC - Cloned rat receptor
HB - Human brain receptor
RPC12 - Rat PC12 receptor
Bold text indicates non-cloned human receptor binding affinities.
mCPP is metabolized via the CYP2D6 isoenzyme by hydroxylation to p-hydroxy-mCPP (OH-mCPP).34 Caution should be exercised in coprescribing inhibitors or substrates of CYP2D6 with drugs such as trazodone and nefazodone that have mCPP as a metabolite.34
mCPP is illegal in Belgium.35
mCPP is legal in the Czech Republic.37
mCPP is illegal in Denmark.38
mCPP is illegal in Finland.
mCPP is illegal in Germany.
mCPP is illegal in Hungary since 2012.04.02.
mCPP is illegal in Japan since 2006.10.13
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 1 April 2008. An amnesty for possession and usage of these drugs remained until October 2008, at which point they became completely illegal.40 However, it is important to note that mCPP is legally used for scientific research.
mCPP is illegal in Norway.
mCPP is illegal in Russia.
mCPP is illegal in Sweden.
mCPP is legal in Poland.
mCPP is not scheduled at the federal level in the United States,41 but it is possible that it could be considered a controlled substance analog of BZP, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.
- 1-Benzylpiperazine (BZP)
- 1-Methyl-4-benzylpiperazine (MBZP)
- 1,4-Dibenzylpiperazine (DBZP)
- 3-Trifluoromethylphenylpiperazine (TFMPP)
- 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)
- 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)
- 4-Fluorophenylpiperazine (pFPP)
- 4-Methoxyphenylpiperazine (MeOPP)
- Etoperidone, Nefazodone, Trazodone - Metabolize into mCPP.
- Quipazine - A related piperazine serotonin agonist.
- Org 12,962
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- Bossong M, Brunt T, Van Dijk J et al. (March 2009). "mCPP: an undesired addition to the ecstasy market". Journal of Psychopharmacology (Oxford, England) 24 (9): 1395–401. doi:10.1177/0269881109102541. PMID 19304863.
- Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ (December 2009). "Content of ecstasy in the Netherlands: 1993-2008". Addiction (Abingdon, England) 104 (12): 2057–66. doi:10.1111/j.1360-0443.2009.02707.x. PMID 19804461.
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- Rajkumar R, Pandey DK, Mahesh R, Radha R (April 2009). "1-(m-Chlorophenyl)piperazine induces depressogenic-like behaviour in rodents by stimulating the neuronal 5-HT(2A) receptors: proposal of a modified rodent antidepressant assay". European Journal of Pharmacology 608 (1-3): 32–41. doi:10.1016/j.ejphar.2009.02.041. PMID 19269287.
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- Hollander E, DeCaria CM, Nitescu A et al. (January 1992). "Serotonergic function in obsessive-compulsive disorder. Behavioral and neuroendocrine responses to oral m-chlorophenylpiperazine and fenfluramine in patients and healthy volunteers". Archives of General Psychiatry 49 (1): 21–8. doi:10.1001/archpsyc.1992.01820010021003. PMID 1728249.
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- 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): 136–139. doi:10.1212/wnl.55.1.136. 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
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- ANVISA resolution - Portaria SVS/MS 344/98
- Misuse of Drugs (Classification of BZP) Amendment Bill 2008
- 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
- Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL