{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{DISPLAYTITLE:''para''-Methoxyphenylpiperazine}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 447725798 | drug_name = pMeOPP | image = pMeOPP.svg | image_class = skin-invert-image | width = 250px | image2 = MeOPP3d.png | image_class2 = bg-transparent | width2 = 200px

<!--Clinical data--> | tradename = | legal_DE = NpSG | legal_NZ = Class C | routes_of_administration = Oral

<!--Pharmacokinetic data--> | metabolism = The human liver P450 CYP2D6 converts para-methoxyphenylpiperazine by demethylation to para-hydroxyphenylpiperazine. | excretion = Renal

<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 38212-30-5 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = P385M92GYG | ATC_prefix = none | PubChem = 269722 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 237180 | synonyms = pMeOPP; pMPP; p-MeOPP; p-MPP; 4-MeOPP; 4-MPP; MeOPP; MPP; Paraperazine

<!--Chemical data--> | IUPAC_name = 1-(4-methoxyphenyl)piperazine | C=11 | H=16 | N=2 | O=1 | SMILES = C1=CC(=CC=C1N2CCNCC2)OC | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C11H16N2O/c1-14-11-4-2-10(3-5-11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = MRDGZSKYFPGAKP-UHFFFAOYSA-N }}

'''''para''-Methoxyphenylpiperazine''' ('''pMeOPP'''), also known as '''4-methoxyphenylpiperazine''' ('''4-MeOPP'''), is a substituted piperazine derivative with stimulant effects which has been sold as an ingredient in "Party pills", initially in New Zealand and subsequently in other countries around the world.<ref name="Elliott2011">{{cite journal | vauthors = Elliott S | title = Current awareness of piperazines: pharmacology and toxicology | journal = Drug Test Anal | volume = 3 | issue = 7–8 | pages = 430–438 | date = 2011 | pmid = 21744514 | doi = 10.1002/dta.307 | url = }}</ref>

==Pharmacology== pMeOPP is anecdotally said to induce significantly less anxiety than similar piperazines, and is usually taken at doses between 120–200&nbsp;mg. However it is often mixed with stimulant piperazine derivatives such as benzylpiperazine (BZP) for a combined effect.

pMeOPP has been found ''in vitro'' to inhibit the reuptake and induce the release of the monoamine neurotransmitters. This is a mechanism of action shared with drugs of abuse such as amphetamines, and pMeOPP produces somewhat similar effects although it is much less potent and is thought to have relatively insignificant abuse potential.<ref>{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 }}</ref> Piperazine derivatives such as trifluoromethylphenylpiperazine (TFMPP) have also been shown to exert a major part of their mechanism of action as nonselective serotonin receptor agonists, and pMeOPP has also been demonstrated to act in this way.<ref>{{cite journal | vauthors = Maurer HH, Kraemer T, Springer D, Staack RF | title = Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis | journal = Therapeutic Drug Monitoring | volume = 26 | issue = 2 | pages = 127–131 | date = April 2004 | pmid = 15228152 | doi = 10.1097/00007691-200404000-00007 | s2cid = 9255084 }}</ref>

==Legal status==

===Finland=== Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>{{cite web | title = Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista | trans-title = Government decree on psychoactive substances banned from the consumer market | language = Finnish | work = Finlex Data Bank | url = https://finlex.fi/fi/lainsaadanto/2014/1130 }}</ref>

===New Zealand=== Based on the recommendation of the EACD, the New Zealand government has passed legislation which placed BZP, along with a number of other piperazine derivatives 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>[http://www.parliament.nz/en-NZ/PB/Legislation/Bills/d/3/d/00DBHOH_BILL8220_1-Misuse-of-Drugs-Classification-of-BZP-Amendment.htm Misuse of Drugs (Classification of BZP) Amendment Bill 2008]</ref>

===United States=== pMeOPP is not scheduled at the federal level in the United States.<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=2014-12-17 |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>

====Florida==== "Methoxyphenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.<ref name="Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL">[http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL]</ref>

== See also == * Substituted piperazine

== References == {{Reflist}}

== Further reading == {{refbegin}} * {{cite journal | vauthors = Harish Chinthal C, Kavitha CN, Yathirajan HS, Foro S, Rathore RS, Glidewell C | title = Fifteen 4-(2-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions: supra-molecular assembly in zero, one, two and three dimensions | journal = Acta Crystallographica Section E: Crystallographic Communications | volume = 76 | issue = Pt 11 | pages = 1779–1793 | date = November 2020 | pmid = 33209353 | doi = 10.1107/S2056989020014097 | publisher = International Union of Crystallography | doi-access = free | pmc = 7643239 | bibcode = 2020AcCrE..76.1779H }} {{refend}}

== External links == * {{Commons category-inline|Para-Methoxyphenylpiperazine}}

{{Stimulants}} {{Monoamine releasing agents}} {{Serotonin receptor modulators}} {{Piperazines}}

{{DEFAULTSORT:Methoxyphenylpiperazine, para-}}

Category:Designer drugs Category:Monoamine releasing agents Category:1-Phenylpiperazines Category:Serotonin receptor agonists