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Para-Methoxyphenylpiperazine

Clinical data
Other names	pMeOPP; pMPP; p-MeOPP; p-MPP; 4-MeOPP; 4-MPP; MeOPP; MPP; Paraperazine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) NZ: Class C
Pharmacokinetic data
Metabolism	The human liver P450 CYP2D6 converts para-methoxyphenylpiperazine by demethylation to para-hydroxyphenylpiperazine.
Excretion	Renal
Identifiers
IUPAC name 1-(4-methoxyphenyl)piperazine
CAS Number	38212-30-5
PubChem CID	269722
ChemSpider	237180
UNII	P385M92GYG
CompTox Dashboard (EPA)	DTXSID30191591
ECHA InfoCard	100.048.918
Chemical and physical data
Formula	C11H16N2O
Molar mass	192.262 g·mol
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1N2CCNCC2)OC
InChI 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 Key:MRDGZSKYFPGAKP-UHFFFAOYSA-N
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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.

Pharmacology

pMeOPP is anecdotally said to induce significantly less anxiety than similar piperazines, and is usually taken at doses between 120–200 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. 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.

Legal status

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".

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.

United States

pMeOPP is not scheduled at the federal level in the United States.

Florida

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

See also

• Substituted piperazine

References

1. Elliott S (2011). "Current awareness of piperazines: pharmacology and toxicology". Drug Test Anal. 3 (7–8): 430–438. doi:10.1002/dta.307. PMID 21744514.
2. 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): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
3. 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): 127–131. doi:10.1097/00007691-200404000-00007. PMID 15228152. S2CID 9255084.
4. "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government decree on psychoactive substances banned from the consumer market]. Finlex Data Bank (in Finnish).
5. Misuse of Drugs (Classification of BZP) Amendment Bill 2008
6. 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
7. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

Further reading

• Harish Chinthal C, Kavitha CN, Yathirajan HS, Foro S, Rathore RS, Glidewell C (November 2020). "Fifteen 4-(2-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions: supra-molecular assembly in zero, one, two and three dimensions". Acta Crystallographica. Section E, Crystallographic Communications. 76 (Pt 11). International Union of Crystallography: 1779–1793. doi:10.1107/S2056989020014097. PMC 7643239. PMID 33209353.

External links

• Media related to Para-Methoxyphenylpiperazine at Wikimedia Commons

• Drugs not assigned an ATC code
• Serotonin receptor agonists
• Monoamine releasing agents
• Designer drugs
• 1-Piperazinyl compounds