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Revision as of 09:03, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CAS_number').← Previous edit Latest revision as of 03:12, 16 December 2024 edit undoOAbot (talk | contribs)Bots440,440 editsm Open access bot: doi updated in citation with #oabot. 
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{{Short description|Stimulant}}
{{DISPLAYTITLE:''meta''-Chlorophenylpiperazine}} {{DISPLAYTITLE:''meta''-Chlorophenylpiperazine}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 415699108 | verifiedrevid = 457790176
| drug_name = ''meta''-Chlorophenylpiperazine
| IUPAC_name = 1-(3-chlorophenyl)piperazine | IUPAC_name = 1-(3-chlorophenyl)piperazine
| image = MCPP.svg | image = MCPP.svg
| width = 150 | width = 185px
| image2 = MCPP3d.png | image2 = MCPP-3D-vdW.png
| width2 = 165px
| drug_name = ''meta''-Chlorophenylpiperazine


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_status = See below..
| legal_BR = F2
| routes_of_administration = Oral, Nasal, Rectal
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_DE = Anlage II
| legal_NZ = <!-- Class A, B, C -->
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_EU =
| routes_of_administration = ], ], ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| metabolism = Hepatic | metabolism = ] (])<ref name="pmid10379419" />
| elimination_half-life = 4–14 hours<ref name="pmid10379419">{{cite journal | vauthors = Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB | title = Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine | journal = Cellular and Molecular Neurobiology | volume = 19 | issue = 4 | pages = 427–442 | date = August 1999 | pmid = 10379419 | doi = 10.1023/a:1006953923305 | s2cid = 19585113 }}</ref><ref name="SchatzbergNemeroff2017">{{cite book|vauthors = Schatzberg AF,Nemeroff CB|title=The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition|url=https://books.google.com/books?id=KfHEDgAAQBAJ&pg=PA460|year=2017|publisher=American Psychiatric Pub|isbn=978-1-58562-523-9|pages=460–}}</ref>
| elimination_half-life = 2-6 hours
| excretion = Renal | excretion = ]


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = changed | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 6640-24-0
| CAS_number_Ref = {{cascite|correct|??}}
| ATC_prefix = None
| CAS_number = <!-- blanked - oldvalue: 51639-49-7 -->
| ATC_prefix = none | ATC_suffix =
| ATC_suffix =
| PubChem = 1355 | PubChem = 1355
| IUPHAR_ligand = 142 | IUPHAR_ligand = 142
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1314 | ChemSpiderID = 1314
| ChEBI_Ref = {{ebicite|changed|EBI}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = REY0CNO998
| KEGG = C11738
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10588 | ChEBI = 10588
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
Line 36: Line 49:


<!--Chemical data--> <!--Chemical data-->
| C=10 | H=13 | Cl=1 | N=2 | C=10 | H=13 | Cl=1 | N=2
| SMILES = Clc1cc(ccc1)N2CCNCC2
| molecular_weight = 196.676 g/mol
| smiles = Clc1cc(ccc1)N2CCNCC2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2 | StdInChI = 1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2
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}} }}


'''''meta''-Chlorophenylpiperazine''' ('''mCPP''') is a ] of the ] class. It was initially developed in the late-1970s and used in ] before being sold as a ] in the mid-2000s.<ref name="pmid16318952">{{cite journal | vauthors = Bossong MG, Van Dijk JP, Niesink RJ | title = Methylone and mCPP, two new drugs of abuse? | journal = Addiction Biology | volume = 10 | issue = 4 | pages = 321–323 | date = December 2005 | pmid = 16318952 | doi = 10.1080/13556210500350794 | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1355-6215&date=2005&volume=10&issue=4&spage=321 | url-status = dead | s2cid = 36169592 | archive-url = https://archive.today/20130105180901/http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1355-6215&date=2005&volume=10&issue=4&spage=321 | archive-date = 2013-01-05 }}</ref><ref name="pmid17348609">{{cite journal | vauthors = Lecompte Y, Evrard I, Arditti J | title = | language = fr | journal = Therapie | volume = 61 | issue = 6 | pages = 523–530 | year = 2006 | pmid = 17348609 | doi = 10.2515/therapie:2006093 }}</ref> It has been detected in pills touted as legal alternatives to illicit ]s in ] and pills sold as "]" in ] and the ].<ref name="pmid19304863">{{cite journal | vauthors = Bossong MG, Brunt TM, Van Dijk JP, Rigter SM, Hoek J, Goldschmidt HM, Niesink RJ | title = mCPP: an undesired addition to the ecstasy market | journal = Journal of Psychopharmacology | volume = 24 | issue = 9 | pages = 1395–1401 | date = September 2010 | pmid = 19304863 | doi = 10.1177/0269881109102541 | s2cid = 11186375 }}</ref><ref name="pmid19804461">{{cite journal | vauthors = Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ | title = Content of ecstasy in the Netherlands: 1993-2008 | journal = Addiction | volume = 104 | issue = 12 | pages = 2057–2066 | date = December 2009 | pmid = 19804461 | doi = 10.1111/j.1360-0443.2009.02707.x | doi-access = free }}</ref>
] in ]]]


Despite its advertisement as a ], mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.<ref name="pmid19304863"/> It lacks any ] effects, but has "psychostimulant, anxiety-provoking, and hallucinogenic effects."<ref>{{Cite web|last=World Health Organization|date=|title=1-(3-chlorophenyl) piperazine (mCPP) - Expert peer review on pre-review report|url=http://158.232.12.119/entity/medicines/areas/quality_safety/5.3cmCPPpre-review.pdf|archive-url=|archive-date=|access-date=2021-01-12|website=}}</ref><ref>{{cite journal | vauthors = Tancer ME, Johanson CE | title = The subjective effects of MDMA and mCPP in moderate MDMA users | journal = Drug and Alcohol Dependence | volume = 65 | issue = 1 | pages = 97–101 | date = December 2001 | pmid = 11714594 | doi = 10.1016/s0376-8716(01)00146-6 }}</ref><ref name="pmid14563541">{{cite journal | vauthors = Tancer M, Johanson CE | title = Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP | journal = Drug and Alcohol Dependence | volume = 72 | issue = 1 | pages = 33–44 | date = October 2003 | pmid = 14563541 | doi = 10.1016/S0376-8716(03)00172-8 }}</ref><ref name="pmid9933142" /> It is also known to produce ], ], and ] effects in rodents and humans,<ref name="pmid19269287">{{cite journal | vauthors = Rajkumar R, Pandey DK, Mahesh R, Radha R | title = 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 | journal = European Journal of Pharmacology | volume = 608 | issue = 1–3 | pages = 32–41 | date = April 2009 | pmid = 19269287 | doi = 10.1016/j.ejphar.2009.02.041 }}</ref><ref name="pmid2767117">{{cite journal | vauthors = Kennett GA, Whitton P, Shah K, Curzon G | title = Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists | journal = European Journal of Pharmacology | volume = 164 | issue = 3 | pages = 445–454 | date = May 1989 | pmid = 2767117 | doi = 10.1016/0014-2999(89)90252-5 }}</ref> and can induce ]s in individuals susceptible to them.<ref name="pmid1756202">{{cite journal | vauthors = Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW | title = Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects | journal = Biological Psychiatry | volume = 30 | issue = 10 | pages = 973–984 | date = November 1991 | pmid = 1756202 | doi = 10.1016/0006-3223(91)90119-7 | s2cid = 43010184 | url = https://zenodo.org/record/1253832 }}</ref><ref name="pmid3110824">{{cite journal | vauthors = Charney DS, Woods SW, Goodman WK, Heninger GR | title = Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects | journal = Psychopharmacology | volume = 92 | issue = 1 | pages = 14–24 | year = 1987 | pmid = 3110824 | doi = 10.1007/bf00215473 | s2cid = 43079787 }}</ref><ref name="pmid17481859">{{cite journal | vauthors = Van Veen JF, Van der Wee NJ, Fiselier J, Van Vliet IM, Westenberg HG | title = Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine (m-CPP) in patients with generalized social anxiety disorder, panic disorder and healthy controls | journal = European Neuropsychopharmacology | volume = 17 | issue = 10 | pages = 637–642 | date = October 2007 | pmid = 17481859 | doi = 10.1016/j.euroneuro.2007.03.005 | s2cid = 41601926 }}</ref><ref name="pmid15336303">{{cite journal | vauthors = van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG | title = Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls | journal = European Neuropsychopharmacology | volume = 14 | issue = 5 | pages = 413–417 | date = October 2004 | pmid = 15336303 | doi = 10.1016/j.euroneuro.2004.01.001 | s2cid = 28987431 }}</ref> It also worsens ] symptoms in people with the disorder.<ref name="pmid1728249">{{cite journal | vauthors = Hollander E, DeCaria CM, Nitescu A, Gully R, Suckow RF, Cooper TB, Gorman JM, Klein DF, Liebowitz MR | display-authors = 6 | title = Serotonergic function in obsessive-compulsive disorder. Behavioral and neuroendocrine responses to oral m-chlorophenylpiperazine and fenfluramine in patients and healthy volunteers | journal = Archives of General Psychiatry | volume = 49 | issue = 1 | pages = 21–28 | date = January 1992 | pmid = 1728249 | doi = 10.1001/archpsyc.1992.01820010021003 }}</ref><ref name="pmid9676822">{{cite journal | vauthors = Broocks A, Pigott TA, Hill JL, Canter S, Grady TA, L'Heureux F, Murphy DL | title = Acute intravenous administration of ondansetron and m-CPP, alone and in combination, in patients with obsessive-compulsive disorder (OCD): behavioral and biological results | journal = Psychiatry Research | volume = 79 | issue = 1 | pages = 11–20 | date = June 1998 | pmid = 9676822 | doi = 10.1016/S0165-1781(98)00029-8 | s2cid = 30339598 | url = https://zenodo.org/record/1259861 }}<!--https://zenodo.org/record/1259861--></ref><ref name="pmid2018816">{{cite journal | vauthors = Pigott TA, Zohar J, Hill JL, Bernstein SE, Grover GN, Zohar-Kadouch RC, Murphy DL | title = Metergoline blocks the behavioral and neuroendocrine effects of orally administered m-chlorophenylpiperazine in patients with obsessive-compulsive disorder | journal = Biological Psychiatry | volume = 29 | issue = 5 | pages = 418–426 | date = March 1991 | pmid = 2018816 | doi = 10.1016/0006-3223(91)90264-M | s2cid = 37648659 }}</ref>
'''''meta''-Chlorophenylpiperazine''' ('''mCPP''') is a ] of the ] class. It was initially developed in the late-1970s and used in ] before being sold as a ] in the mid-2000s.<ref name="pmid16318952">{{cite journal | author = Bossong MG, Van Dijk JP, Niesink RJ | title = Methylone and mCPP, two new drugs of abuse? | journal = ] | volume = 10 | issue = 4 | pages = 321–3 | year = 2005 | month = December | pmid = 16318952 | doi = 10.1080/13556210500350794 | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1355-6215&date=2005&volume=10&issue=4&spage=321}}</ref><ref name="pmid17348609">{{cite journal | author = Lecompte Y, Evrard I, Arditti J | title = | language = French | journal = Thérapie | volume = 61 | issue = 6 | pages = 523–30 | year = 2006 | pmid = 17348609 | doi = | url = }}</ref> It has been detected in pills touted as legal alternatives to illicit ]s in ] and pills sold as "]" in ] and the ].<ref name="pmid19304863">{{cite journal | author = Bossong M, Brunt T, Van Dijk J, ''et al.'' | title = mCPP: an undesired addition to the ecstasy market | journal = Journal of Psychopharmacology (Oxford, England) | volume = 24| issue = 9| pages = 1395–401| year = 2009 | month = March | pmid = 19304863 | doi = 10.1177/0269881109102541 | url = http://jop.sagepub.com/cgi/pmidlookup?view=long&pmid=19304863}}</ref><ref name="pmid19804461">{{cite journal | author = Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ | title = Content of ecstasy in the Netherlands: 1993-2008 | journal = Addiction (Abingdon, England) | volume = 104 | issue = 12 | pages = 2057–66 | year = 2009 | month = December | pmid = 19804461 | doi = 10.1111/j.1360-0443.2009.02707.x | url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0965-2140&date=2009&volume=104&issue=12&spage=2057}}</ref>


Despite its advertisement as a ], mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.<ref name="pmid19304863"/> It lacks any ] effects,<ref name="pmid14563541">{{cite journal | author = Tancer M, Johanson CE | title = Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP | journal = Drug and Alcohol Dependence | volume = 72 | issue = 1 | pages = 33–44 | year = 2003 | month = October | pmid = 14563541 | doi = 10.1016/S0376-8716(03)00172-8| url = http://linkinghub.elsevier.com/retrieve/pii/S0376871603001728}}</ref> produces ] and ] effects in rodents and humans,<ref name="pmid19269287">{{cite journal | author = Rajkumar R, Pandey DK, Mahesh R, Radha R | title = 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 | journal = European Journal of Pharmacology | volume = 608 | issue = 1-3 | pages = 32–41 | year = 2009 | month = April | pmid = 19269287 | doi = 10.1016/j.ejphar.2009.02.041 | url = http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(09)00198-8}}</ref><ref name="pmid2767117">{{cite journal | author = Kennett GA, Whitton P, Shah K, Curzon G | title = Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists | journal = European Journal of Pharmacology | volume = 164 | issue = 3 | pages = 445–54 | year = 1989 | month = May | pmid = 2767117 | doi = 10.1016/0014-2999(89)90252-5| url = }}</ref> and can induce ]s in individuals susceptible to them.<ref name="pmid1756202">{{cite journal | author = Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW | title = Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects | journal = Biological Psychiatry | volume = 30 | issue = 10 | pages = 973–84 | year = 1991 | month = November | pmid = 1756202 | doi = 10.1016/0006-3223(91)90119-7| url = }}</ref><ref name="pmid3110824">{{cite journal | author = Charney DS, Woods SW, Goodman WK, Heninger GR | title = Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects | journal = Psychopharmacology | volume = 92 | issue = 1 | pages = 14–24 | year = 1987 | pmid = 3110824 | doi = | url = }}</ref><ref name="pmid17481859">{{cite journal | author = Van Veen JF, Van der Wee NJ, Fiselier J, Van Vliet IM, Westenberg HG | title = Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine (m-CPP) in patients with generalized social anxiety disorder, panic disorder and healthy controls | journal = European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology | volume = 17 | issue = 10 | pages = 637–42 | year = 2007 | month = October | pmid = 17481859 | doi = 10.1016/j.euroneuro.2007.03.005 | url = http://linkinghub.elsevier.com/retrieve/pii/S0924-977X(07)00082-X}}</ref><ref name="pmid15336303">{{cite journal | author = van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG | title = Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls | journal = European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology | volume = 14 | issue = 5 | pages = 413–7 | year = 2004 | month = October | pmid = 15336303 | doi = 10.1016/j.euroneuro.2004.01.001 | url = http://linkinghub.elsevier.com/retrieve/pii/S0924977X0400015X}}</ref> It also worsens ] symptoms in people with the disorder.<ref name="pmid1728249">{{cite journal | author = Hollander E, DeCaria CM, Nitescu A, ''et al.'' | title = Serotonergic function in obsessive-compulsive disorder. Behavioral and neuroendocrine responses to oral m-chlorophenylpiperazine and fenfluramine in patients and healthy volunteers | journal = Archives of General Psychiatry | volume = 49 | issue = 1 | pages = 21–8 | year = 1992 | month = January | pmid = 1728249 | doi = | url = http://archpsyc.ama-assn.org/cgi/pmidlookup?view=long&pmid=1728249}}</ref><ref name="pmid9676822">{{cite journal | author = Broocks A, Pigott TA, Hill JL, ''et al.'' | title = Acute intravenous administration of ondansetron and m-CPP, alone and in combination, in patients with obsessive-compulsive disorder (OCD): behavioral and biological results | journal = Psychiatry Research | volume = 79 | issue = 1 | pages = 11–20 | year = 1998 | month = June | pmid = 9676822 | doi = 10.1016/S0165-1781(98)00029-8| url = http://linkinghub.elsevier.com/retrieve/pii/S0165178198000298}}</ref><ref name="pmid2018816">{{cite journal | author = Pigott TA, Zohar J, Hill JL, ''et al.'' | title = Metergoline blocks the behavioral and neuroendocrine effects of orally administered m-chlorophenylpiperazine in patients with obsessive-compulsive disorder | journal = Biological Psychiatry | volume = 29 | issue = 5 | pages = 418–26 | year = 1991 | month = March | pmid = 2018816 | doi = 10.1016/0006-3223(91)90264-M| url = }}</ref> mCPP is known to induce ]s in humans and has been used for testing potential ] medications.<ref name="Leone">{{cite journal | vauthors = Leone M, Attanasio A, Croci D, Filippini G, D'Amico D, Grazzi L, Nespolo A, Bussone G | display-authors = 6 | title = The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study | journal = Neurology | volume = 55 | issue = 1 | pages = 136–139 | date = July 2000 | pmid = 10891925 | doi = 10.1212/wnl.55.1.136 | s2cid = 27617431 }}</ref><ref name="Martin et al.">{{cite journal | vauthors = Martin RS, Martin GR | title = 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) | journal = Cephalalgia | volume = 21 | issue = 1 | pages = 46–52 | date = February 2001 | pmid = 11298663 | doi = 10.1046/j.1468-2982.2001.00157.x | s2cid = 8471836 | doi-access = free }}</ref><ref name="Petkov et al.">{{cite journal | vauthors = Petkov VD, Belcheva S, Konstantinova E | title = Anxiolytic effects of dotarizine, a possible antimigraine drug | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 17 | issue = 10 | pages = 659–668 | date = December 1995 | pmid = 9053586 }}</ref> It has potent ] effects and has encouraged the development of selective ] ]s for the treatment of ] as well.<ref name="pmid2906446">{{cite journal | vauthors = Kennett GA, Curzon G | title = 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 | journal = Psychopharmacology | volume = 96 | issue = 1 | pages = 93–100 | year = 1988 | pmid = 2906446 | doi = 10.1007/BF02431539 | s2cid = 21417374 }}</ref><ref name="pmid9361339">{{cite journal | vauthors = Sargent PA, Sharpley AL, Williams C, Goodall EM, Cowen PJ | title = 5-HT2C receptor activation decreases appetite and body weight in obese subjects | journal = Psychopharmacology | volume = 133 | issue = 3 | pages = 309–312 | date = October 1997 | pmid = 9361339 | doi = 10.1007/s002130050407 | url = http://link.springer.de/link/service/journals/00213/bibs/7133003/71330309.htm | url-status = dead | s2cid = 7125577 | archive-url = https://web.archive.org/web/20020112063624/http://link.springer.de/link/service/journals/00213/bibs/7133003/71330309.htm | archive-date = 2002-01-12 }}</ref><ref name="pmid15719229">{{cite journal | vauthors = Hayashi A, Suzuki M, Sasamata M, Miyata K | title = Agonist diversity in 5-HT(2C) receptor-mediated weight control in rats | journal = Psychopharmacology | volume = 178 | issue = 2–3 | pages = 241–249 | date = March 2005 | pmid = 15719229 | doi = 10.1007/s00213-004-2019-z | s2cid = 7580231 }}</ref><ref name="pmid17209663">{{cite journal | vauthors = Halford JC, Harrold JA, Boyland EJ, Lawton CL, Blundell JE | title = Serotonergic drugs : effects on appetite expression and use for the treatment of obesity | journal = Drugs | volume = 67 | issue = 1 | pages = 27–55 | year = 2007 | pmid = 17209663 | doi = 10.2165/00003495-200767010-00004 | s2cid = 46972692 }}</ref>


{{TOC limit|3}}
mCPP is known to induce ]s in humans and has been used for testing potential ] medications.<ref name="Leone">{{cite journal | last = Leone | first = M | 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 = 136–139 | date = July 12, 2000 | url = | doi = | pmid = 10891925}}</ref><ref name="Martin et al.">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</ref><ref name="Petkov et al.">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.</ref> It has potent ] effects and has encouraged the development of selective ] ]s for the treatment of ] as well.<ref name="pmid2906446">{{cite journal | author = Kennett GA, Curzon G | title = 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 | journal = Psychopharmacology | volume = 96 | issue = 1 | pages = 93–100 | year = 1988 | pmid = 2906446 | doi = 10.1007/BF02431539| url = }}</ref><ref name="pmid9361339">{{cite journal | author = Sargent PA, Sharpley AL, Williams C, Goodall EM, Cowen PJ | title = 5-HT2C receptor activation decreases appetite and body weight in obese subjects | journal = Psychopharmacology | volume = 133 | issue = 3 | pages = 309–12 | year = 1997 | month = October | pmid = 9361339 | doi = 10.1007/s002130050407| url = http://link.springer.de/link/service/journals/00213/bibs/7133003/71330309.htm}}</ref><ref name="pmid15719229">{{cite journal | author = Hayashi A, Suzuki M, Sasamata M, Miyata K | title = Agonist diversity in 5-HT(2C) receptor-mediated weight control in rats | journal = Psychopharmacology | volume = 178 | issue = 2-3 | pages = 241–9 | year = 2005 | month = March | pmid = 15719229 | doi = 10.1007/s00213-004-2019-z | DUPLICATE DATA: doi = 10.1007/s00213-004-2019-z}}</ref><ref name="pmid17209663">{{cite journal | author = Halford JC, Harrold JA, Boyland EJ, Lawton CL, Blundell JE | title = Serotonergic drugs : effects on appetite expression and use for the treatment of obesity | journal = Drugs | volume = 67 | issue = 1 | pages = 27–55 | year = 2007 | pmid = 17209663 | doi = | url = http://content.wkhealth.com/linkback/openurl?issn=0012-6667&volume=67&issue=1&spage=27}}</ref>


==Pharmacology==
''Meta''-chlorophenylpiperazine is a major metabolite of the psychotropic drug ], and may be responsible for some of its side-effects, such as headaches and migraines induced many hours after initial consumption.


===Pharmacodynamics===
== Pharmacology ==
{| class="wikitable floatleft" style="font-size:small;"
|+ ''meta''-Chlorophenylpiperazine<ref name="PDSP">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP) | vauthors = Roth BL, Driscol J |author1-link=Bryan Roth | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 14 August 2017 | url = https://pdsp.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testDDRadio=testDDRadio&testLigandDD=1827&testLigand=&refDDRadio=refDDRadio&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query}}</ref>
|-
! Site !! K<sub>i</sub> (nM) !! Species !! Refs
|-
| {{abbrlink|SERT|Serotonin transporter}} || 202–432 || Human || <ref name="pmid9400006">{{cite journal | vauthors = Owens MJ, Morgan WN, Plott SJ, Nemeroff CB | title = Neurotransmitter receptor and transporter binding profile of antidepressants and their metabolites | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 283 | issue = 3 | pages = 1305–1322 | date = December 1997 | pmid = 9400006 }}</ref>
|-
| {{abbrlink|NET|Norepinephrine transporter}} || 1,940–4,360 || Human || <ref name="pmid9400006" />
|-
| {{abbrlink|DAT|Dopamine transporter}} || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || 44–400 || Human || <ref name="PDSP" /><ref name="pmid2537663">{{cite journal | vauthors = Hamik A, Peroutka SJ | title = 1-(m-chlorophenyl)piperazine (mCPP) interactions with neurotransmitter receptors in the human brain | journal = Biological Psychiatry | volume = 25 | issue = 5 | pages = 569–575 | date = March 1989 | pmid = 2537663 | doi = 10.1016/0006-3223(89)90217-5 | s2cid = 46730665 | doi-access = free }}</ref>
|-
| ] || 89–501 || Human || <ref name="PDSP" /><ref name="pmid7984267">{{cite journal | vauthors = Boess FG, Martin IL | title = Molecular biology of 5-HT receptors | journal = Neuropharmacology | volume = 33 | issue = 3–4 | pages = 275–317 | year = 1994 | pmid = 7984267 | doi = 10.1016/0028-3908(94)90059-0 | s2cid = 35553281 }}</ref>
|-
| ] || 210–1,300 || Human || <ref name="pmid2537663" /><ref name="pmid1652050">{{cite journal | vauthors = Hamblin MW, Metcalf MA | title = Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor | journal = Molecular Pharmacology | volume = 40 | issue = 2 | pages = 143–148 | date = August 1991 | pmid = 1652050 }}</ref>
|-
| ] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || 32–398 || Human || <ref name="PDSP" /><ref name="pmid9933142" /><ref name="pmid2537663" /><ref name="pmid7582481">{{cite journal | vauthors = Bonhaus DW, Bach C, DeSouza A, Salazar FH, Matsuoka BD, Zuppan P, Chan HW, Eglen RM | display-authors = 6 | title = The pharmacology and distribution of human 5-hydroxytryptamine2B (5-HT2B) receptor gene products: comparison with 5-HT2A and 5-HT2C receptors | journal = British Journal of Pharmacology | volume = 115 | issue = 4 | pages = 622–628 | date = June 1995 | pmid = 7582481 | pmc = 1908489 | doi = 10.1111/j.1476-5381.1995.tb14977.x }}</ref>
|-
| ] || 3.2–63 || Human || <ref name="PDSP" /><ref name="pmid11104741">{{cite journal | vauthors = Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL | title = Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications | journal = Circulation | volume = 102 | issue = 23 | pages = 2836–2841 | date = December 2000 | pmid = 11104741 | doi = 10.1161/01.cir.102.23.2836 | doi-access = free }}</ref><ref name="pmid10498829">{{cite journal | vauthors = Porter RH, Benwell KR, Lamb H, Malcolm CS, Allen NH, Revell DF, Adams DR, Sheardown MJ | display-authors = 6 | title = Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells | journal = British Journal of Pharmacology | volume = 128 | issue = 1 | pages = 13–20 | date = September 1999 | pmid = 10498829 | pmc = 1571597 | doi = 10.1038/sj.bjp.0702751 }}</ref>
|-
| ] || 3.4–251 || Human || <ref name="PDSP" /><ref name="pmid9933142" /><ref name="pmid7582481" /><ref name="pmid15081042">{{cite journal | vauthors = 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 | display-authors = 6 | title = Indoline derivatives as 5-HT(2C) receptor agonists | journal = Bioorganic & Medicinal Chemistry Letters | volume = 14 | issue = 9 | pages = 2367–2370 | date = May 2004 | pmid = 15081042 | doi = 10.1016/j.bmcl.2003.05.001 }}</ref>
|-
| ] || 427 || Human || <ref name="PDSP" />
|-
| ] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ]&nbsp;<!--Spacing--> || 1,354 || Human || <ref name="PDSP" />
|-
| ] || 1,748 || Human || <ref name="PDSP" />
|-
| ] || 163 || Human || <ref name="PDSP" />
|-
| ] || 97–2,900 || Human || <ref name="pmid9400006" /><ref name="pmid2537663" />
|-
| &nbsp;&nbsp;] || 1,386 || Human || <ref name="PDSP" />
|-
| &nbsp;&nbsp;] || 915 || Human || <ref name="PDSP" />
|-
| &nbsp;&nbsp;] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || 112–570 || Human || <ref name="pmid9400006" /><ref name="pmid2537663" />
|-
| &nbsp;&nbsp;] || 145 || Human || <ref name="PDSP" />
|-
| &nbsp;&nbsp;] || 106 || Human || <ref name="PDSP" />
|-
| &nbsp;&nbsp;] || 124 || Human || <ref name="PDSP" />
|-
| ] || 2,500 || Human || <ref name="pmid2537663" />
|-
| &nbsp;&nbsp;] || 2,359 || Human || <ref name="PDSP" />
|-
| &nbsp;&nbsp;] || 3,474 || Human || <ref name="PDSP" />
|-
| ] || 7,000 || Human || <ref name="pmid2537663" />
|-
| ] || >10,000 || Human || <ref name="pmid2537663" />
|-
| ] || >10,000 || Rat || <ref name="PDSP" />
|-
| ] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || >10,000 || Human || <ref name="PDSP" />
|-
| ] || 326 || Human || <ref name="PDSP" />
|-
| ] || >10,000 || Human || <ref name="pmid2537663" />
|-
| {{abbrlink|nAChRs|Nicotinic acetylcholine receptors}} || >10,000 || Human || <ref name="PDSP" />
|-
| ] || {{abbr|ND|No data}} || {{abbr|ND|No data}} || {{abbr|ND|No data}}
|-
| ] || 8,350 || Rat || <ref name="PDSP" />
|-
| ] || 759 || Rat || <ref name="PDSP" />
|-
| {{abbrlink|VDCC|Voltage-dependent calcium channel}} || 6,043 || Rat || <ref name="PDSP" />
|- class="sortbottom"
| colspan="4" style="width: 1px;" | Values are K<sub>i</sub> (nM). The smaller the value, the more strongly the drug binds to the site.
|}


mCPP possesses significant ] for the ], ], ], ], ], ], ], and ]s, as well as the ].<ref name="urlPDSP Database - UNC">{{cite web | url = http://pdsp.med.unc.edu/pdsp.php#search | title = PDSP Database - UNC | format = | work = | accessdate = }}</ref> It also has some affinity for ], ], ], ], and ].<ref name="urlPDSP Database - UNC"/><ref name="pmid7814826">{{cite journal | author = Silverstone PH, Rue JE, Franklin M, ''et al.'' | title = The effects of administration of mCPP on psychological, cognitive, cardiovascular, hormonal and MHPG measurements in human volunteers | journal = International Clinical Psychopharmacology | volume = 9 | issue = 3 | pages = 173–8 | year = 1994 | month = September | pmid = 7814826 | doi = 10.1097/00004850-199409000-00005| url = }}</ref> It behaves as an ] at most or all serotonin receptors.<ref name="urlPDSP Database - UNC"/><ref name="pmid503247">{{cite journal | author = Samanin R, Mennini T, Ferraris A, Bendotti C, Borsini F, Garattini S | title = Chlorophenylpiperazine: a central serotonin agonist causing powerful anorexia in rats | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 308 | issue = 2 | pages = 159–63 | year = 1979 | month = August | pmid = 503247 | doi = 10.1007/BF00499059| url = }}</ref><ref name="pmid15888508">{{cite journal | author = Odagaki Y, Toyoshima R, Yamauchi T | title = Trazodone and its active metabolite m-chlorophenylpiperazine as partial agonists at 5-HT1A receptors assessed by GTPgammaS binding | journal = Journal of Psychopharmacology (Oxford, England) | volume = 19 | issue = 3 | pages = 235–41 | year = 2005 | month = May | pmid = 15888508 | doi = 10.1177/0269881105051526 | url = http://jop.sagepub.com/cgi/pmidlookup?view=long&pmid=15888508}}</ref> mCPP has been shown to act not only as a ] of serotonin but as a ] as well.<ref name="pmid6610423">{{cite journal | author = Pettibone DJ, Williams M | title = Serotonin-releasing effects of substituted piperazines in vitro | journal = Biochemical Pharmacology | volume = 33 | issue = 9 | pages = 1531–5 | year = 1984 | month = May | pmid = 6610423 | doi = 10.1016/0006-2952(84)90424-6| url = http://linkinghub.elsevier.com/retrieve/pii/0006-2952(84)90424-6}}</ref> mCPP possesses significant ] for the ], ], ], ], ], ], ], and ]s, as well as the ].<ref name="PDSP" /> It also has some affinity for ], ], ], ], and ].<ref name="PDSP" /><ref name="pmid7814826">{{cite journal | vauthors = Silverstone PH, Rue JE, Franklin M, Hallis K, Camplin G, Laver D, Cowen PJ | title = The effects of administration of mCPP on psychological, cognitive, cardiovascular, hormonal and MHPG measurements in human volunteers | journal = International Clinical Psychopharmacology | volume = 9 | issue = 3 | pages = 173–178 | date = September 1994 | pmid = 7814826 | doi = 10.1097/00004850-199409000-00005 | s2cid = 25464507 }}</ref> It behaves as an ] at most serotonin receptors.<ref name="pmid503247">{{cite journal | vauthors = Samanin R, Mennini T, Ferraris A, Bendotti C, Borsini F, Garattini S | title = Chlorophenylpiperazine: a central serotonin agonist causing powerful anorexia in rats | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 308 | issue = 2 | pages = 159–163 | date = August 1979 | pmid = 503247 | doi = 10.1007/BF00499059 | s2cid = 19293115 }}</ref><ref name="pmid15888508">{{cite journal | vauthors = Odagaki Y, Toyoshima R, Yamauchi T | title = Trazodone and its active metabolite m-chlorophenylpiperazine as partial agonists at 5-HT1A receptors assessed by GTPgammaS binding | journal = Journal of Psychopharmacology | volume = 19 | issue = 3 | pages = 235–241 | date = May 2005 | pmid = 15888508 | doi = 10.1177/0269881105051526 | s2cid = 27389008 }}</ref> mCPP has been shown to act not only as a ] but as a ] as well.<ref name="pmid6610423">{{cite journal | vauthors = Pettibone DJ, Williams M | title = Serotonin-releasing effects of substituted piperazines in vitro | journal = Biochemical Pharmacology | volume = 33 | issue = 9 | pages = 1531–1535 | date = May 1984 | pmid = 6610423 | doi = 10.1016/0006-2952(84)90424-6 }}</ref>


mCPP's strongest actions are at the 5-HT<sub>2B</sub> and 5-HT<sub>2C</sub> receptors and its discriminative cue is mediated primarily by 5-HT<sub>2C</sub>.<ref name="urlPDSP Database - UNC"/><ref name="pmid8082704">{{cite journal | author = Callahan PM, Cunningham KA | title = Involvement of 5-HT2C receptors in mediating the discriminative stimulus properties of m-chlorophenylpiperazine (mCPP) | journal = European Journal of Pharmacology | volume = 257 | issue = 1-2 | pages = 27–38 | year = 1994 | month = May | pmid = 8082704 | doi = 10.1016/0014-2999(94)90690-4| url = http://linkinghub.elsevier.com/retrieve/pii/0014-2999(94)90690-4}}</ref><ref name="pmid9683007">{{cite journal | author = Gommans J, Hijzen TH, Maes RA, Olivier B | title = Discriminative stimulus properties of mCPP: evidence for a 5-HT2C receptor mode of action | journal = Psychopharmacology | volume = 137 | issue = 3 | pages = 292–302 | year = 1998 | month = June | pmid = 9683007 | doi = 10.1007/s002130050622| url = http://link.springer.de/link/service/journals/00213/bibs/8137003/81370292.htm}}</ref> Its negative effects such as ], ]s, and ] are likely mediated by its actions on the 5-HT<sub>2C</sub> receptor,<ref name="pmid2767117">{{cite journal | author = Kennett GA, Whitton P, Shah K, Curzon G | title = Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists | journal = European Journal of Pharmacology | volume = 164 | issue = 3 | pages = 445–54 | year = 1989 | month = May | pmid = 2767117 | doi = 10.1016/0014-2999(89)90252-5| url = }}</ref><ref name="pmid2906446">{{cite journal | author = Kennett GA, Curzon G | title = 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 | journal = Psychopharmacology | volume = 96 | issue = 1 | pages = 93–100 | year = 1988 | pmid = 2906446 | doi = 10.1007/BF02431539| url = }}</ref><ref name="pmid3401632">{{cite journal | author = Kennett GA, Curzon G | title = Evidence that mCPP may have behavioural effects mediated by central 5-HT1C receptors | journal = British Journal of Pharmacology | volume = 94 | issue = 1 | pages = 137–47 | year = 1988 | month = May | pmid = 3401632 | pmc = 1853919 | doi = | url = }}</ref> whereas its ] effects at high doses are caused by 5-HT<sub>2A</sub> activation. Other effects of mCPP include ], ], and ], the latter two the result of increased 5-HT<sub>2C</sub> activity and the former likely via 5-HT<sub>3</sub> stimulation.<ref name="pmid2775468">{{cite journal | author = Kłodzińska A, Jaros T, Chojnacka-Wójcik E, Maj J | title = Exploratory hypoactivity induced by m-trifluoromethylphenylpiperazine (TFMPP) and m-chlorophenylpiperazine (m-CPP) | journal = Journal of Neural Transmission. Parkinson's Disease and Dementia Section | volume = 1 | issue = 3 | pages = 207–18 | year = 1989 | pmid = 2775468 | doi = 10.1007/BF02248670| url = }}</ref><ref name="pmid7862925">{{cite journal | author = Walsh AE, Smith KA, Oldman AD, Williams C, Goodall EM, Cowen PJ | title = m-Chlorophenylpiperazine decreases food intake in a test meal | journal = Psychopharmacology | volume = 116 | issue = 1 | pages = 120–2 | year = 1994 | month = September | pmid = 7862925 | doi = 10.1007/BF02244883| url = }}</ref><ref name="pmid8001637">{{cite journal | author = Stancampiano R, Melis MR, Argiolas A | title = Penile erection and yawning induced by 5-HT1C receptor agonists in male rats: relationship with dopaminergic and oxytocinergic transmission | journal = European Journal of Pharmacology | volume = 261 | issue = 1-2 | pages = 149–55 | year = 1994 | month = August | pmid = 8001637 | doi = 10.1016/0014-2999(94)90313-1| url = http://linkinghub.elsevier.com/retrieve/pii/0014-2999(94)90313-1}}</ref> mCPP's strongest actions are at the 5-HT<sub>2B</sub> and 5-HT<sub>2C</sub> receptors and its discriminative cue is mediated primarily by 5-HT<sub>2C</sub>.<ref name="PDSP"/><ref name="pmid8082704">{{cite journal | vauthors = Callahan PM, Cunningham KA | title = Involvement of 5-HT2C receptors in mediating the discriminative stimulus properties of m-chlorophenylpiperazine (mCPP) | journal = European Journal of Pharmacology | volume = 257 | issue = 1–2 | pages = 27–38 | date = May 1994 | pmid = 8082704 | doi = 10.1016/0014-2999(94)90690-4 }}</ref><ref name="pmid9683007">{{cite journal | vauthors = Gommans J, Hijzen TH, Maes RA, Olivier B | title = Discriminative stimulus properties of mCPP: evidence for a 5-HT2C receptor mode of action | journal = Psychopharmacology | volume = 137 | issue = 3 | pages = 292–302 | date = June 1998 | pmid = 9683007 | doi = 10.1007/s002130050622 | url = http://link.springer.de/link/service/journals/00213/bibs/8137003/81370292.htm | url-status = dead | s2cid = 9265150 | archive-url = https://web.archive.org/web/20020112104011/http://link.springer.de/link/service/journals/00213/bibs/8137003/81370292.htm | archive-date = 2002-01-12 }}</ref> Its negative effects such as ], ]s, and ] are likely mediated by its actions on the 5-HT<sub>2C</sub> receptor.<ref name="pmid2767117"/><ref name="pmid2906446"/><ref name="pmid3401632">{{cite journal | vauthors = Kennett GA, Curzon G | title = Evidence that mCPP may have behavioural effects mediated by central 5-HT1C receptors | journal = British Journal of Pharmacology | volume = 94 | issue = 1 | pages = 137–147 | date = May 1988 | pmid = 3401632 | pmc = 1853919 | doi = 10.1111/j.1476-5381.1988.tb11508.x }}</ref> Other effects of mCPP include ], ], and ], the latter two the result of increased 5-HT<sub>2C</sub> activity and the former likely via 5-HT<sub>3</sub> stimulation.<ref name="pmid2775468">{{cite journal | vauthors = Kłodzińska A, Jaros T, Chojnacka-Wójcik E, Maj J | title = Exploratory hypoactivity induced by m-trifluoromethylphenylpiperazine (TFMPP) and m-chlorophenylpiperazine (m-CPP) | journal = Journal of Neural Transmission. Parkinson's Disease and Dementia Section | volume = 1 | issue = 3 | pages = 207–218 | year = 1989 | pmid = 2775468 | doi = 10.1007/BF02248670 | s2cid = 23471213 }}</ref><ref name="pmid7862925">{{cite journal | vauthors = Walsh AE, Smith KA, Oldman AD, Williams C, Goodall EM, Cowen PJ | title = m-Chlorophenylpiperazine decreases food intake in a test meal | journal = Psychopharmacology | volume = 116 | issue = 1 | pages = 120–122 | date = September 1994 | pmid = 7862925 | doi = 10.1007/BF02244883 | s2cid = 40801166 }}</ref><ref name="pmid8001637">{{cite journal | vauthors = Stancampiano R, Melis MR, Argiolas A | title = Penile erection and yawning induced by 5-HT1C receptor agonists in male rats: relationship with dopaminergic and oxytocinergic transmission | journal = European Journal of Pharmacology | volume = 261 | issue = 1–2 | pages = 149–155 | date = August 1994 | pmid = 8001637 | doi = 10.1016/0014-2999(94)90313-1 }}</ref>


In comparison studies, mCPP has approximately 10-fold ] for the human 5-HT<sub>2C</sub> receptor over the human 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors (K<sub>i</sub> = 3.4&nbsp;nM vs. 32.1 and 28.8&nbsp;nM).<ref name="pmid9933142">{{cite journal | vauthors = Nelson DL, Lucaites VL, Wainscott DB, Glennon RA | title = Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 359 | issue = 1 | pages = 1–6 | date = January 1999 | pmid = 9933142 | doi = 10.1007/pl00005315 | s2cid = 20150858 }}</ref> It acts as a ] of the human 5-HT<sub>2A</sub><ref>{{cite journal | vauthors = Grotewiel MS, Chu H, Sanders-Bush E | title = m-chlorophenylpiperazine and m-trifluoromethylphenylpiperazine are partial agonists at cloned 5-HT2A receptors expressed in fibroblasts | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 271 | issue = 2 | pages = 1122–1126 | date = November 1994 | pmid = 7965773 | url = https://pubmed.ncbi.nlm.nih.gov/7965773/ | access-date = 2022-10-02 }}</ref> and 5-HT<sub>2C</sub><ref>{{cite journal | vauthors = Porter RH, Benwell KR, Lamb H, Malcolm CS, Allen NH, Revell DF, Adams DR, Sheardown MJ | display-authors = 6 | title = Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells | journal = British Journal of Pharmacology | volume = 128 | issue = 1 | pages = 13–20 | date = September 1999 | pmid = 10498829 | pmc = 1571597 | doi = 10.1038/sj.bjp.0702751 }}</ref> receptors but as an ] of the human 5-HT<sub>2B</sub> receptors.<ref name="pmid8856697">{{cite journal | vauthors = Thomas DR, Gager TL, Holland V, Brown AM, Wood MD | title = m-Chlorophenylpiperazine (mCPP) is an antagonist at the cloned human 5-HT2B receptor | journal = NeuroReport | volume = 7 | issue = 9 | pages = 1457–1460 | date = June 1996 | pmid = 8856697 | doi = 10.1097/00001756-199606170-00002 }}</ref>
== Pharmacokinetics ==


mCPP is metabolized via the ] ] by ] to p-hydroxy-mCPP (OH-mCPP).<ref name="pmid9836023">{{cite journal | author = Rotzinger S, Fang J, Coutts RT, Baker GB | title = Human CYP2D6 and metabolism of m-chlorophenylpiperazine | journal = Biological Psychiatry | volume = 44 | issue = 11 | pages = 1185–91 | year = 1998 | month = December | pmid = 9836023 | doi = 10.1016/S0006-3223(97)00483-6| url = http://linkinghub.elsevier.com/retrieve/pii/S0006-3223(97)00483-6}}</ref> Caution should be exercised in coprescribing ] with drugs such as ] and ] that have mCPP as a metabolite.<ref name="pmid9836023" /> Despite acting as a serotonin 5-HT<sub>2A</sub> receptor agonist, mCPP has been described as non-hallucinogenic.<ref name="GumpperRoth2024">{{cite journal | vauthors = Gumpper RH, Roth BL | title = Psychedelics: preclinical insights provide directions for future research | journal = Neuropsychopharmacology | volume = 49 | issue = 1 | pages = 119–127 | date = January 2024 | pmid = 36932180 | doi = 10.1038/s41386-023-01567-7 | url = }}</ref> However, hallucinations have occasionally been reported when large doses of mCPP are taken.<ref name="GumpperRoth2024" />


===Pharmacokinetics===
== Legal status ==
mCPP is ] via the ] ] by ] to ''para''-hydroxy-mCPP (''p''-OH-mCPP) and this plays a major role in its metabolism.<ref name="pmid10379419" /><ref name="pmid9836023">{{cite journal | vauthors = Rotzinger S, Fang J, Coutts RT, Baker GB | title = Human CYP2D6 and metabolism of m-chlorophenylpiperazine | journal = Biological Psychiatry | volume = 44 | issue = 11 | pages = 1185–1191 | date = December 1998 | pmid = 9836023 | doi = 10.1016/S0006-3223(97)00483-6 | s2cid = 45097940 }}</ref><ref name="pmid21744514" /> The ] of mCPP is 4 to 14&nbsp;hours.<ref name="pmid10379419" />


mCPP is a ] of a variety of other piperazine drugs including ], ], ], ], ], ], ], and ].<ref name="pmid21744514">{{cite journal | vauthors = Elliott S | title = Current awareness of piperazines: pharmacology and toxicology | journal = Drug Testing and Analysis | volume = 3 | issue = 7–8 | pages = 430–438 | year = 2011 | pmid = 21744514 | doi = 10.1002/dta.307 }}</ref>{{Additional citation needed|date=September 2017}} It is formed by ] via ].<ref name="pmid21744514" /> Caution should be exercised in concomitant administration of ] ] such as ], ], ], and ] 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.<ref name="pmid9836023" /><ref name="pmid10379419" />
*In Finland: Illegal
* In the Netherlands: Illegal
* In the United States: Legal
* In Denmark: Illegal<ref>
</ref>
* In Germany: Illegal
* In Russia: Illegal
* In Sweden: Legal
* In Norway: Illegal
* In Brazil: Illegal<ref></ref>
* In Belgium: Illegal<ref></ref>
* In the Czech Republic: Legal<ref></ref>


==Chemistry==
Based on the recommendation of the ], 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.<ref></ref>

===Analogues===
]s of mCPP include:


== See also ==
* ] (BZP) * ] (BZP)
* ] (MBZP) * ] (MBZP)
Line 91: Line 180:
* ] (pFPP) * ] (pFPP)
* ] (MeOPP) * ] (MeOPP)

* ], ], ] - Metabolize into mCPP.
Some additional analogues include ], ], and ].
* ] - A related piperazine serotonin agonist.

* ]
==Society and culture==
] in ].]]
] in ] at the end of 2008.]]

===Legal status===

====Belgium====
mCPP is illegal in Belgium.<ref>{{Cite web|url=http://www.emcdda.europa.eu//html.cfm//index5176EN.html?sLanguageISO=EN&nNodeID=5176&pluginMethod=eldd.shownewsdetails&id=20/12/2006BELGIUM:+New+substances+controlled+include+mCPP+and+khat|title=EMCDDA &#124; News|website=www.emcdda.europa.eu}}</ref>

====Brazil====
mCPP is illegal in ].<ref>{{Cite web|url=http://www.anvisa.gov.br/divulga/noticias/2008/051108_2.htm|title=ANVISA resolution - Portaria SVS/MS 344/98}}</ref>

====Canada====
mCPP is not a controlled drug in Canada.

====China====
As of October 2015 mCPP is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | url-status=dead }}</ref>

====Czech Republic====
mCPP is legal in the Czech Republic.<ref>{{Cite web|url=http://www.mzcr.cz/Odbornik/obsah/legislativa_1051_3.html|title=Legislativa|website=www.mzcr.cz}}</ref>

====Denmark====
mCPP is illegal in Denmark.<ref>{{Cite web|url=https://www.erowid.org/psychoactives/law/countries/denmark/denmark_law_info1.shtml|title=Erowid Psychoactive Vaults : Law : Countries : Denmark (DK) : Denmark bans 2C-T-4, TFMPP, BZP, mCPP, MeOPP|website=www.erowid.org}}</ref>{{unreliable source?|date=May 2016}}

====Finland====
mCPP is illegal in ].

====Germany====
mCPP is illegal in ].

====Hungary====
mCPP is illegal in ] since 2012.

====Japan====
mCPP is illegal in ] since 2006.

====Netherlands====
mCPP is legal in ].<ref>{{Cite web|url=https://wetten.overheid.nl/BWBR0001941/2017-05-25|title=Opiumwet|first=Ministerie van Binnenlandse Zaken en|last=Koninkrijksrelaties|website=wetten.overheid.nl}}</ref>

====New Zealand====
Based on the recommendation of the ], 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.<ref>{{Cite web|url=http://www.parliament.nz/en-NZ/PB/Legislation/Bills/d/3/d/00DBHOH_BILL8220_1-Misuse-of-Drugs-Classification-of-BZP-Amendment.htm|title=Misuse of Drugs (Classification of BZP) Amendment Bill 2008}}</ref> However, mCPP is legally used for scientific research.

====Norway====
mCPP is illegal in ].

====Russia====
mCPP is illegal in ].

====Sweden====
mCPP is illegal in ].

====Poland====
mCPP is illegal in ].

====United States====
mCPP is not scheduled at the federal level in the ],<ref name="PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I">{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I. |access-date=2014-12-18 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref> but it is possible that it could be considered a controlled substance analog of ], in which case purchase, sale, or possession could be prosecuted under the ].

However, "chlorophenylpiperazine" is a Schedule I ] in the state of ] making it illegal to buy, sell, or possess in this state.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">{{Cite web|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|title=Statutes & Constitution :View Statutes : Online Sunshine|website=leg.state.fl.us}}</ref>

====Turkey====
mCPP is illegal in ] since 20/05/2009.<ref>{{Cite web|url=https://www.resmigazete.gov.tr/eskiler/2009/05/20090520-3.htm|title = Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü}}</ref>

== See also ==
* ]


== References == == References ==
{{Reflist|2}} {{Reflist}}

== External links ==
* {{Commons category-inline}}


{{Drug use}} {{Drug use}}
{{Monoamine releasing agents}}
{{Hallucinogens}}
{{Serotonin receptor modulators}}
{{Serotonergics}}
{{Piperazines}}


{{DEFAULTSORT:Chlorophenylpiperazine, Meta-}} {{DEFAULTSORT:Chlorophenylpiperazine, Meta-}}

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