para-Methoxyphenylpiperazine

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
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • NZ: Class C
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
IUPAC name
  • 1-(4-methoxyphenyl)piperazine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.048.918
Chemical and physical data
FormulaC11H16N2O
Molar mass192.262 g·mol−1
3D model (JSmol)
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 N
  • Key:MRDGZSKYFPGAKP-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Pharmacology

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, however it is often mixed with stimulant piperazine derivatives such as benzylpiperazine (BZP) for a combined effect.

MeOPP 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 MeOPP produces somewhat similar effects although it is much less potent and is thought to have relatively insignificant abuse potential.[1] 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 MeOPP has also been demonstrated to act in this way.[2]

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.[3]

United States

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

Florida

"Methoxyphenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[5]

See also

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

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

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

References
  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. PMID 17223101.
  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. PMID 15228152. S2CID 9255084.
  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
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.