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. 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]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market". [3]

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. [4]

United States

MeOPP is not scheduled at the federal level in the United States. [5]

Florida

"Methoxyphenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [6]

See also

Related Research Articles

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union, Australia, and New Zealand, as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids.

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

Benzylpiperazine (BZP) is a substance often used as a recreational drug and is known to have euphoriant and stimulant properties. Several studies conducted between 2000 and 2011 found that the effects of BZP are similar to amphetamine, although BZP's dosage is roughly 10 times higher by weight.

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

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

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

Party pills, also known as "herbal highs", "pep pills" "dance pills" and "natural power", is a colloquialism for a type of recreational drug whose main ingredient was originally benzylpiperazine (BZP), but has expanded to a wide range of compounds with a variety of effects. BZP is banned in several countries, including the USA, Republic of Ireland, Australia and New Zealand, but is available on a more or less restricted basis in many jurisdictions. A range of other piperazine derivatives have also been sold as ingredients in party pills, and many of these branded "proprietary blends" have subsequently been sold in countries around the world.

<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.

α-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 produces highly stimulating effects in humans, based on the experiences of the individuals who have tried it. Most of the individuals who have tried it prefer α-PVP to it, but prefer this drug over α-PVT. It is said to lack euphoria compared to α-PVP.

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

para-Fluorophenylpiperazine is a piperazine derivative with mildly psychedelic and euphoriant effects. It has been sold as an ingredient in legal recreational drugs known as "Party pills", initially in New Zealand and subsequently in other countries around the world.

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

Methylbenzylpiperazine is a stimulant drug which is a derivative of benzylpiperazine. MBZP has been sold as an ingredient in legal recreational drugs known as "party pills", initially in New Zealand and subsequently in other countries around the world.

<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.

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

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; monoamine releasing agents can induce the release of one or more of these neurotransmitters.

<span class="mw-page-title-main">Substituted phenethylamine</span> Chemical class of organic compounds

Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted cathinones, or simply cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

<span class="mw-page-title-main">4-Methylmethylphenidate</span> Stimulant drug

threo-4-Methylmethylphenidate (4-MeTMP) is a stimulant drug related to methylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking dopamine reuptake despite its high binding affinity, which led to its investigation as a possible substitute drug for treatment of stimulant abuse. On the other hand, several other simple ring-substituted derivatives of threo-methylphenidate such as the 4-fluoro and 3-chloro compounds are more potent than methylphenidate both in efficacy as dopamine reuptake inhibitors and in animal drug discrimination assays.

<span class="mw-page-title-main">Methiopropamine</span> Structural analog of methamphetamine

Methiopropamine (MPA) is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position. It appeared for public sale in the UK in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.

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>-Methoxyphenylpiperazine Serotonergic drug

ortho-Methoxyphenylpiperazine (oMeOPP), also known as 2-methoxyphenylpiperazine (2-MeOPP), is a phenylpiperazine derivative which is known to act as a serotonergic agent. Along with various other phenylpiperazines, like benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP), oMeOPP has been found in illicit drug samples.

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): 132–137. 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): 127–131. doi:10.1097/00007691-200404000-00007. PMID   15228152. S2CID   9255084.
  3. "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government decree on psychoactive substances banned from the consumer market]. Finlex Data Bank (in Finnish).
  4. Misuse of Drugs (Classification of BZP) Amendment Bill 2008
  5. 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  6. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

Further reading