Meta-Chlorophenylpiperazine

meta-Chlorophenylpiperazine
Clinical data
Routes of
administration		Oral, intranasal, rectal
ATC code
  • None
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
Pharmacokinetic data
MetabolismLiver (CYP2D6)[1]
Elimination half-life4–14 hours[1][2]
ExcretionUrine
Identifiers
IUPAC name
  • 1-(3-chlorophenyl)piperazine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.026.959
Edit this at Wikidata
Chemical and physical data
FormulaC10H13ClN2
Molar mass196.68 g·mol−1
3D model (JSmol)
SMILES
  • Clc1cc(ccc1)N2CCNCC2
InChI
  • InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2 checkY
  • Key:VHFVKMTVMIZMIK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[3][4] 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.[5][6]

Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.[5] It lacks any reinforcing effects, but has "psychostimulant, anxiety-provoking, and hallucinogenic effects."[7][8][9][10] It is also known to produce dysphoric, depressive, and anxiogenic effects in rodents and humans,[11][12] and can induce panic attacks in individuals susceptible to them.[13][14][15][16] It also worsens obsessive–compulsive symptoms in people with the disorder.[17][18][19]

mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications.[20][21][22] It has potent anorectic effects and has encouraged the development of selective 5-HT2C receptor agonists for the treatment of obesity as well.[23][24][25][26]

Pharmacology

Pharmacodynamics

meta-Chlorophenylpiperazine[27]
SiteKi (nM)SpeciesRefs
SERT202–432Human[28]
NET1,940–4,360Human[28]
DATNDNDND
5-HT1A44–400Human[27][29]
5-HT1B89–501Human[27][30]
5-HT1D210–1,300Human[29][31]
5-HT1ENDNDND
5-HT1FNDNDND
5-HT2A32–398Human[27][10][29][32]
5-HT2B3.2–63Human[27][33][34]
5-HT2C3.4–251Human[27][10][32][35]
5-HT3427Human[27]
5-HT4NDNDND
5-HT5A 1,354Human[27]
5-HT61,748Human[27]
5-HT7163Human[27]
α197–2,900Human[28][29]
  α1A1,386Human[27]
  α1B915Human[27]
  α1DNDNDND
α2112–570Human[28][29]
  α2A145Human[27]
  α2B106Human[27]
  α2C124Human[27]
β2,500Human[29]
  β12,359Human[27]
  β23,474Human[27]
D17,000Human[29]
D2>10,000Human[29]
D3>10,000Rat[27]
D4NDNDND
D5>10,000Human[27]
H1326Human[27]
mAChRs>10,000Human[29]
nAChRs>10,000Human[27]
σ1NDNDND
σ28,350Rat[27]
I1759Rat[27]
VDCC6,043Rat[27]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

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.[27] It also has some affinity for α1-adrenergic, α2-adrenergic, H1, I1, and NET.[27][36] It behaves as an agonist at most serotonin receptors.[37][38] mCPP has been shown to act not only as a serotonin reuptake inhibitor but as a serotonin releasing agent as well.[39]

mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.[27][40][41] Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor.[12][23][42] 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.[43][44][45]

In comparison studies, mCPP has approximately 10-fold selectivity for the human 5-HT2C receptor over the human 5-HT2A and 5-HT2B receptors (Ki = 3.4 nM vs. 32.1 and 28.8 nM).[10] It acts as a partial agonist of the human 5-HT2A and 5-HT2C[46] receptors but as an antagonist of the human 5-HT2B receptors.[47]

Pharmacokinetics

mCPP is metabolized via the CYP2D6 isoenzyme by hydroxylation to para-hydroxy-mCPP (p-OH-mCPP) and this plays a major role in its metabolism.[1][48][49] The elimination half-life of mCPP is 4 to 14 hours.[1]

mCPP is a metabolite of a variety of other piperazine drugs including trazodone, nefazodone, etoperidone, enpiprazole, mepiprazole, cloperidone, peraclopone, and BRL-15,572.[49] It is formed by dealkylation via CYP3A4.[49] Caution should be exercised in concomitant administration of CYP2D6 inhibitors such as bupropion, fluoxetine, paroxetine, and thioridazine with drugs that produce mCPP as a metabolite as these drugs are known to increase concentrations of the parent molecule (e.g., trazodone) and of mCPP.[48][1]

Chemistry

Analogues

Analogues of mCPP include:

Some additional analogues include quipazine, ORG-12962, and 3C-PEP.

Society and culture

Tablets containing mCPP confiscated by the DEA in Vernon Hills, Illinois.
Tablets containing mCPP confiscated by the Kriminalpolizei in Europe at the end of 2008.

Belgium

mCPP is illegal in Belgium.[50]

Brazil

mCPP is illegal in Brazil.[51]

Canada

mCPP is not a controlled drug in Canada.

China

As of October 2015 mCPP is a controlled substance in China.[52]

Czech Republic

mCPP is legal in the Czech Republic.[53]

Denmark

mCPP is illegal in Denmark.[54]

Finland

mCPP is illegal in Finland.

Germany

mCPP is illegal in Germany.

Hungary

mCPP is illegal in Hungary since 2012.

Japan

mCPP is illegal in Japan since 2006.

Netherlands

mCPP is legal in the Netherlands.[55]

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.[56] However, it is important to note that mCPP is legally used for scientific research.

Norway

mCPP is illegal in Norway.

Russia

mCPP is illegal in Russia.

Sweden

mCPP is illegal in Sweden.

Poland

mCPP is illegal in Poland.

United States

mCPP is not scheduled at the federal level in the United States,[57] 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.

However, "chlorophenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in this state.[58]

Turkey

mCPP is illegal in Turkey since 20/05/2009.[59]

See also

References

  1. 1 2 3 4 5 Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB (August 1999). "Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine". Cell Mol Neurobiol. 19 (4): 427–42. doi:10.1023/a:1006953923305. PMID 10379419. S2CID 19585113.
  2. ↑ Schatzberg AF, Nemeroff CB (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition. American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9.
  3. ↑ Bossong MG, Van Dijk JP, Niesink RJ (December 2005). "Methylone and mCPP, two new drugs of abuse?". Addiction Biology. 10 (4): 321–3. doi:10.1080/13556210500350794. PMID 16318952. S2CID 36169592. Archived from the original on 2013-01-05.
  4. ↑ 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.
  5. 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. S2CID 11186375.
  6. ↑ Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ (December 2009). "Content of ecstasy in the Netherlands: 1993-2008". Addiction. 104 (12): 2057–66. doi:10.1111/j.1360-0443.2009.02707.x. PMID 19804461.
  7. ↑ World Health Organization. "1-(3-chlorophenyl) piperazine (mCPP) - Expert peer review on pre-review report" (PDF). Retrieved 2021-01-12.{{cite web}}: CS1 maint: url-status (link)
  8. ↑ Tancer, M. E.; Johanson, C. E. (2001-12-01). "The subjective effects of MDMA and mCPP in moderate MDMA users". Drug and Alcohol Dependence. 65 (1): 97–101. doi:10.1016/s0376-8716(01)00146-6. ISSN 0376-8716. PMID 11714594.
  9. ↑ 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.
  10. 1 2 3 4 Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch. Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID 9933142. S2CID 20150858.
  11. ↑ 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.
  12. 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.
  13. ↑ 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. S2CID 43010184.
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  16. ↑ van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG (October 2004). "Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls". European Neuropsychopharmacology. 14 (5): 413–7. doi:10.1016/j.euroneuro.2004.01.001. PMID 15336303. S2CID 28987431.
  17. ↑ 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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  23. 1 2 Kennett GA, Curzon G (1988). "Evidence that hypophagia induced by mCPP and TFMPP requires 5-HT1C and 5-HT1B receptors; hypophagia induced by RU 24969 only requires 5-HT1B receptors". Psychopharmacology. 96 (1): 93–100. doi:10.1007/BF02431539. PMID 2906446. S2CID 21417374.
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  34. ↑ Porter RH, Benwell KR, Lamb H, Malcolm CS, Allen NH, Revell DF, Adams DR, Sheardown MJ (1999). "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells". Br. J. Pharmacol. 128 (1): 13–20. doi:10.1038/sj.bjp.0702751. PMC 1571597. PMID 10498829.
  35. ↑ Bentley JM, Adams DR, Bebbington D, Benwell KR, Bickerdike MJ, Davidson JE, Dawson CE, Dourish CT, Duncton MA, Gaur S, George AR, Giles PR, Hamlyn RJ, Kennett GA, Knight AR, Malcolm CS, Mansell HL, Misra A, Monck NJ, Pratt RM, Quirk K, Roffey JR, Vickers SP, Cliffe IA (2004). "Indoline derivatives as 5-HT(2C) receptor agonists". Bioorg. Med. Chem. Lett. 14 (9): 2367–70. doi:10.1016/j.bmcl.2003.05.001. PMID 15081042.
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  46. ↑ Porter, R. H.; Benwell, K. R.; Lamb, H.; Malcolm, C. S.; Allen, N. H.; Revell, D. F.; Adams, D. R.; Sheardown, M. J. (September 1999). "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells". British Journal of Pharmacology. 128 (1): 13–20. doi:10.1038/sj.bjp.0702751. ISSN 0007-1188. PMC 1571597. PMID 10498829.
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  50. ↑ "EMCDDA | News". www.emcdda.europa.eu.
  51. ↑ "ANVISA resolution - Portaria SVS/MS 344/98".
  52. ↑ "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.
  53. ↑ "Legislativa". www.mzcr.cz.
  54. ↑ "Erowid Psychoactive Vaults : Law : Countries : Denmark (DK) : Denmark bans 2C-T-4, TFMPP, BZP, mCPP, MeOPP". www.erowid.org.
  55. ↑ Koninkrijksrelaties, Ministerie van Binnenlandse Zaken en. "Opiumwet". wetten.overheid.nl.
  56. ↑ "Misuse of Drugs (Classification of BZP) Amendment Bill 2008".
  57. ↑ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  58. ↑ "Statutes & Constitution :View Statutes : Online Sunshine". leg.state.fl.us.
  59. ↑ "Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü".
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