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{{Short description|Chemical compound}}
{{DISPLAYTITLE:''para''-Methoxyphenylpiperazine}}
{{DISPLAYTITLE:''para''-Methoxyphenylpiperazine}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid =355197191
| verifiedrevid =447725798
| IUPAC_name = 1-(4-methoxyphenyl)piperazine
| IUPAC_name = 1-(4-methoxyphenyl)piperazine
| image = MeOPP.svg
| image = MeOPP.svg
Line 9: Line 11:
<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| legal_DE = NpSG
| legal_status = Class C (New Zealand)
| legal_NZ = Class C
| routes_of_administration = Oral
| routes_of_administration = Oral


Line 17: Line 20:


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 38212-30-5
| CAS_number = 38212-30-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P385M92GYG
| ATC_prefix = none
| ATC_prefix = none
| PubChem = 269722
| PubChem = 269722
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 237180
| ChemSpiderID = 237180



<!--Chemical data-->
<!--Chemical data-->
| C=11 | H=16 | N=2 | O=1
| C=11 | H=16 | N=2 | O=1
| molecular_weight = 192.258 g/mol
| smiles = C1=CC(=CC=C1N2CCNCC2)OC
| smiles = C1=CC(=CC=C1N2CCNCC2)OC
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI = 1/C11H16N2O/c1-14-11-4-2-10(3-5-11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3
| InChIKey = MRDGZSKYFPGAKP-UHFFFAOYAD
| 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
| 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
| StdInChIKey = MRDGZSKYFPGAKP-UHFFFAOYSA-N
}}
}}
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'''''para''-Methoxyphenylpiperazine''' ('''MeOPP''', '''pMPP''', '''4-MPP'''; '''Paraperazine''') is a [[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.
'''''para''-Methoxyphenylpiperazine''' ('''MeOPP''', '''pMPP''', '''4-MPP'''; '''Paraperazine''') is a [[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.


==Pharmacology==
⚫
MeOPP has been found ''in vitro'' to [[reuptake inhibitor|inhibit]] the [[reuptake]] and induce the [[releasing agent|release]] of the [[monoamine]] [[neurotransmitter]]s. This is a mechanism of action shared with drugs of abuse such as [[amphetamines]], and MeOPP produces somewhat similar effects although it is much less potent and is thought to have relatively insignificant abuse potential.<ref>Nagai F, Nonaka R, Satoh Hisashi Kamimura K.The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.European Journal of Pharmacology.2006Dec12;[Epubaheadofprint]</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 agonist]]s, and MeOPP has also been demonstrated to act in this way.<ref>Maurer HH, Kraemer T, Springer D, Staack RF.Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis.Therapeutic Drug Monitoring.2004Apr;26(2):127-31.</ref>MeOPPisanecdotallysaidtoinducesignificantlylessanxietythansimilarpiperazines,andisusuallytakenatdosesbetween120–200&nbsp;mg.It does not produceprominent stimulant effects, but is instead said toberelaxing,{{Citationneeded|date=December 2007}}however it is often mixed with stimulant piperazine derivatives such as [[benzylpiperazine]] (BZP) for a combined effect.
MeOPP is anecdotally said to induce significantly less anxiety than similar piperazines, and is usually taken at doses between 120–200&nbsp;mg. It does not produce prominent stimulant effects, but is instead said to be relaxing,{{Citation needed|date=December 2007}} however it is often mixed with stimulant piperazine derivatives such as [[benzylpiperazine]] (BZP) for a combined effect.


⚫
MeOPP has been found ''in vitro'' to [[reuptake inhibitor|inhibit]] the [[reuptake]] and induce the [[releasing agent|release]] of the [[monoamine]] [[neurotransmitter]]s. This is a mechanism of action shared with drugs of abuse such as [[amphetamines]], and MeOPP 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 = 132–7 | 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 agonist]]s, and MeOPP 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=127–31|date=April2004|pmid=15228152|doi=10.1097/00007691-200404000-00007|s2cid=9255084}}</ref>

==Legal status==

===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>
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>


==Seealso==
===UnitedStates===
MeOPP is not scheduled at the federal level in the [[United States]].<ref name= "PART 1308 — SCHEDULES OF CONTROLLED SUBSTANCES - 1308.11 Schedule I" >[http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.]</ref>
* [[1-Benzylpiperazine]] (BZP)

* [[1-Methyl-4-benzylpiperazine]] (MBZP)
====Florida====
* [[1,4-Dibenzylpiperazine]] (DBZP)
"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>
* [[1-(3-Chlorophenyl)piperazine|3-Chlorophenylpiperazine]] (mCPP)

* [[3-Trifluoromethylphenylpiperazine]] (TFMPP)
== See also ==
* [[3,4-Methylenedioxy-1-benzylpiperazine]] (MDBZP)
* [[Substituted piperazine]]
* [[4-Bromo-2,5-dimethoxy-1-benzylpiperazine]] (2C-B-BZP)
*Acta Crystallogr. (2020). E'''76''', 1779-1793
* [[pFPP|4-Fluorophenylpiperazine]] (pFPP)

<nowiki>https://doi.org/10.1107/S2056989020014097</nowiki>

=== Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions ===
C. Harish Chinthal, C. N. Kavitha, H. S. Yathirajan, S. Foro, R. S. Rathore and C. Glidewell

Acta Crystallogr. (2019). E'''75''', 1494-1506

<nowiki>https://doi.org/10.1107/S2056989019012702</nowiki>

=== Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions ===
H. Kiran Kumar, H. S. Yathirajan, S. Foro and C. Glidewell


==References==
==References==
{{Reflist}}
{{Reflist}}


==External links==
{{Entactogens}}
*{{Commons category-inline|Para-Methoxyphenylpiperazines}}
{{Hallucinogens}}

{{Adrenergics}}
{{Dopaminergics}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{Serotonergics}}
{{Serotonin receptor modulators}}
{{Piperazines}}
{{Piperazines}}


{{DEFAULTSORT:Methoxyphenylpiperazine, para-}}
{{DEFAULTSORT:Methoxyphenylpiperazine, para-}}
[[Category:Piperazines]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin receptor agonists]]
[[Category:Phenolethers]]
[[Category:Monoaminereleasing agents]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:1-Piperazinyl compounds]]

Latest revision as of 20:49, 24 July 2023

Para-Methoxyphenylpiperazine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Pharmacokineticdata
MetabolismHepatic
ExcretionRenal
Identifiers
  • 1-(4-methoxyphenyl)piperazine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.048.918Edit this at Wikidata
Chemical and physical data
FormulaC11H16N2O
Molar mass192.262g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1N2CCNCC2)OC
  • InChI=1S/C11H16N2O/c1-14-11-4-2-10(3-5-11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3☒N
  • Key:MRDGZSKYFPGAKP-UHFFFAOYSA-N☒N
☒NcheckY(what is this?)(verify)

para-Methoxyphenylpiperazine(MeOPP,pMPP,4-MPP;Paraperazine) is apiperazinederivative withstimulanteffects which has been sold as an ingredient in "Party pills",initially inNew Zealandand subsequently in other countries around the world.

Pharmacology[edit]

MeOPP is anecdotally said to induce significantly less anxiety than similar piperazines, and is usually taken at doses between 120–200 mg. It does not produce prominent stimulant effects, but is instead said to be relaxing,[citation needed]however it is often mixed with stimulant piperazine derivatives such asbenzylpiperazine(BZP) for a combined effect.

MeOPP has been foundin vitrotoinhibitthereuptakeand induce thereleaseof themonoamineneurotransmitters.This is a mechanism of action shared with drugs of abuse such asamphetamines,and MeOPP produces somewhat similar effects although it is much less potent and is thought to have relatively insignificant abuse potential.[1]Piperazine derivatives such astrifluoromethylphenylpiperazine(TFMPP) have also been shown to exert a major part of their mechanism of action as nonselectiveserotonin receptor agonists,and MeOPP has also been demonstrated to act in this way.[2]

Legal status[edit]

New Zealand[edit]

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.[3]

United States[edit]

MeOPP is not scheduled at the federal level in theUnited States.[4]

Florida[edit]

"Methoxyphenylpiperazine" is a Schedule Icontrolled substancein the state ofFloridamaking it illegal to buy, sell, or possess in Florida.[5]

See also[edit]

https://doi.org/10.1107/S2056989020014097

Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions[edit]

C. Harish Chinthal, C. N. Kavitha, H. S. Yathirajan, S. Foro, R. S. Rathore and C. Glidewell

Acta Crystallogr. (2019). E75,1494-1506

https://doi.org/10.1107/S2056989019012702

Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions[edit]

H. Kiran Kumar, H. S. Yathirajan, S. Foro and C. Glidewell

References[edit]

  1. ^Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain".European Journal of Pharmacology.559(2–3): 132–7.doi:10.1016/j.ejphar.2006.11.075.PMID17223101.
  2. ^Maurer HH, Kraemer T, Springer D, Staack RF (April 2004). "Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis".Therapeutic Drug Monitoring.26(2): 127–31.doi:10.1097/00007691-200404000-00007.PMID15228152.S2CID9255084.
  3. ^Misuse of Drugs (Classification of BZP) Amendment Bill 2008
  4. ^21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  5. ^Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Para-Methoxyphenylpiperazine&oldid=1166957079"