Clinical data
Routes of
Oral, Nasal, Rectal
ATC code none
Legal status
Legal status
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 2-6 hours
Excretion Renal
CAS Number 6640-24-0 N
PubChem (CID) 1355
ChemSpider 1314 YesY
ChEBI CHEBI:10588 YesY
ECHA InfoCard 100.026.959
Chemical and physical data
Formula C10H13ClN2
Molar mass 196.676 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)
Tablets containing mCPP confiscated by the DEA in Vernon Hills, Illinois

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.[1][2] 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.[3][4]

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,[6][7] and can induce panic attacks in individuals susceptible to them.[8][9][10][11] It also worsens obsessive-compulsive symptoms in people with the disorder.[12][13][14]

mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications.[15][16][17] It has potent anorectic effects and has encouraged the development of selective 5-HT2C receptor agonists for the treatment of obesity as well.[18][19][20][21]


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.[22][23] It behaves as an agonist at most or all serotonin receptors.[22][24][25] 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.[22][27][28] Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor,[7][18][29] whereas its psychedelic effects at high doses are caused by 5-HT2A activation. However, there is also evidence for mCPP antagonism of the 5-HT2A receptor, suggesting an indirect mechanism for the drug's psychedelic effects.[30] 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.[31][32][33]

Binding affinity (Ki [nM]) towards cloned human receptors where data is available

Protein Ki (nM)[34]
SERT 265.1
NET 3150
5-HT1A 43.9
5-HT1B 251.9
5-HT1D 285.5
5-HT2A 54.5
5-HT2B 30.3
5-HT2C 13.04
5-HT3 427
5-HT5A 1354
5-HT6 1748
5-HT7 162.5
α1A 1386
α1B 914.6
α2A 145.1
α2B 105.8
α2C 123.5
β1 2359
β2 3474
D1 7000 (HB)
D2 >10000 (HB)
D3 >10000 (RC)
D5 >10000
BZD receptor >10000 (HB)
I1 758.9 (RPC12)
σ2 8350 (RPC12)
H1 326.3
mAChRs >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).[35] Caution should be exercised in coprescribing inhibitors or substrates of CYP2D6 with drugs such as trazodone and nefazodone that have mCPP as a metabolite.[35]


Trazodone, Nefazodone, Mepiprazole, cloperidone, peraclopone,

A fluanisone analog, in which the o-Anisyl was replaced with m-chlorophenyl is described in Ex7 U.S. Patent 2,997,472 (1961).


mCPP is illegal in Belgium.[36]


mCPP is illegal in Brazil.[37]


As of October 2015 mCPP is a controlled substance in China.[38]

Czech Republic

mCPP is legal in the Czech Republic.[39]


mCPP is illegal in Denmark.[40]


mCPP is illegal in Finland.


mCPP is illegal in Germany.


mCPP is illegal in Hungary since 2012.


mCPP is illegal in Japan since 2006.


mCPP is not illegal in the Netherlands.[41]

New Zealand

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.[42] 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 illegal in Poland.

United States

mCPP is not scheduled at the federal level in the United States,[43] 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.


"Chlorophenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[44]

See also


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  2. Lecompte Y, Evrard I, Arditti J (2006). "[Metachlorophenylpiperazine (mCPP): a new designer drug]". Thérapie (in French). 61 (6): 523–30. doi:10.2515/therapie:2006093. PMID 17348609.
  3. 1 2 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.
  4. 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.
  5. Tancer M, Johanson CE (October 2003). "Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP". Drug and Alcohol Dependence. 72 (1): 33–44. doi:10.1016/S0376-8716(03)00172-8. PMID 14563541.
  6. 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.
  7. 1 2 Kennett GA, Whitton P, Shah K, Curzon G (May 1989). "Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists". European Journal of Pharmacology. 164 (3): 445–54. doi:10.1016/0014-2999(89)90252-5. PMID 2767117.
  8. Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW (November 1991). "Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects". Biological Psychiatry. 30 (10): 973–84. doi:10.1016/0006-3223(91)90119-7. PMID 1756202.
  9. Charney DS, Woods SW, Goodman WK, Heninger GR (1987). "Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects". Psychopharmacology. 92 (1): 14–24. doi:10.1007/bf00215473. PMID 3110824.
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  36. EMCDDA
  37. ANVISA resolution - Portaria SVS/MS 344/98
  38. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
  41. Misuse of Drugs (Classification of BZP) Amendment Bill 2008
  43. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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