Para-Methoxyphenylpiperazine

Last updated
Para-Methoxyphenylpiperazine
MeOPP.svg
MeOPP3d.png
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
Metabolism Hepatic
Excretion Renal
Identifiers
  • 1-(4-methoxyphenyl)piperazine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.918 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H16N2O
Molar mass 192.262 g·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 X mark.svgN
  • Key:MRDGZSKYFPGAKP-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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.

Contents

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,[ citation needed ] 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

Related Research Articles

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<span class="mw-page-title-main">Stimulant</span> Overarching term covers many drugs that increase activity of the central nervous system

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<span class="mw-page-title-main">Club drug</span> Category of recreational drugs

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<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

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<span class="mw-page-title-main">Benzylpiperazine</span> Recreational drug

Benzylpiperazine (BZP) is a recreational drug with euphoriant and stimulant properties. The effects produced by BZP are comparable to those produced by amphetamine. Adverse effects have been reported following its use including acute psychosis, renal toxicity and seizures. Deaths from piperazine derivatives are extremely rare, but there has been at least one death apparently due to BZP alone. Its sale is banned in several countries, including Australia, Canada, New Zealand, the United States, the Republic of Ireland, the United Kingdom, Bulgaria, Romania and other parts of Europe.

<span class="mw-page-title-main">Trifluoromethylphenylpiperazine</span> Chemical compound

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<span class="mw-page-title-main">Party pills</span> Type of recreational drugs

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<i>meta</i>-Chlorophenylpiperazine Stimulant

meta-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s. It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as "ecstasy" in Europe and the United States.

<i>alpha</i>-Pyrrolidinopropiophenone Chemical compound

α-Pyrrolidinopropiophenone (α-PPP), is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and presumably also produces these effects in humans, based on the context in which it has been found.

<i>para</i>-Fluorophenylpiperazine Chemical compound

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<span class="mw-page-title-main">Piberaline</span> Chemical compound

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<span class="mw-page-title-main">Methylbenzylpiperazine</span> Chemical compound

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<span class="mw-page-title-main">2C-B-BZP</span> Chemical compound

4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". It produces stimulant effects similar to those of benzylpiperazine (BZP).

<span class="mw-page-title-main">Dibenzylpiperazine</span> Chemical compound

Dibenzylpiperazine (DBZP) is a piperazine derivative often found as an impurity in the recreational stimulant drug benzylpiperazine (BZP). Presence of DBZP is a marker for low quality or badly made BZP. It can be made as a reaction byproduct during BZP synthesis, either because the reaction has been run at too high a temperature, or because an excess of benzyl chloride has been used.

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Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research.

<i>ortho</i>-Methylphenylpiperazine Chemical compound

ortho-Methylphenylpiperazine (also known as oMPP, oMePP, 1-(2-methylphenyl)piperazine, 2-MPP, and 2-MePP) is a psychoactive designer drug of the phenylpiperazine group. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC50 values for induction of monoamine release of 175 nM for serotonin, 39.1 nM for norepinephrine, and 296–542 nM for dopamine. As such, it has about 4.5-fold preference for induction of norepinephrine release over serotonin, and about 7.6- to 13.9-fold preference for induction of norepinephrine release over dopamine.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

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