meta- chlorophenylpiperazine

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Structural formula
Structural formula of m-CPP
General
Surname meta- chlorophenylpiperazine
other names
  • 1- (3-chlorophenyl) piperazine
  • m-CPP
Molecular formula C 10 H 13 ClN 2
External identifiers / databases
CAS number 6640-24-0
EC number 229-654-7
ECHA InfoCard 100,026,959
PubChem 1355
Wikidata Q286112
Drug information
Drug class

Piperazine derivatives

Mechanism of action

5-HT receptor agonist

properties
Molar mass 196.68 g · mol -1
safety instructions
GHS labeling of hazardous substances
09 - Dangerous for the environment

Caution

H and P phrases H: 411
P: 273-391-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

meta- chlorophenylpiperazine ( m-CPP ) is a derivative of piperazine . Because of its psychoactive effects, it appears as an ingredient in party drugs , mostly in tablet form.

use

In experiments with test persons who had a history of migraine attacks, it was found that these attacks can be triggered artificially in about 90% of test persons after administration of m-CPP.

The substance m-CPP also appears as an MDMA substitute or additive in ecstasy tablets, and since 2008 also in combination with MCP ( metoclopramide ) to suppress the nausea that can appear when the psychotropic effects set in. The danger of the substance m-CPP lies in the overdosing of the reloading common among ecstasy users (scene jargon). The tablets, which ideally contain MDMA, are habitually dosed in high doses during an evening or night, which can undoubtedly lead to further side effects even with MDMA, but according to the latest studies by the University of Bristol in relation to the side effects and especially long-term consequences of m-CPP abuse. The long-term damage and long-term effects of m-CPP have so far hardly been researched; this also applies to the other psychoactive piperazine derivatives.

Ingenious underground laboratories are constantly looking for new substances that have not yet been banned under narcotics law or are under official supervision, in order to then bring them onto the black market as another new drug. In the last few years alone, since 2005 for the first time on various websites with the topic of party drugs and education about the like, warnings about tablets containing m-CPP and sold as ecstasy, the warning messages on the Internet keep increasing.

Other piperazine derivatives have also been found more frequently as ingredients in recreational drugs, mainly in tablets sold as ecstasy, the most important ones being 1-benzylpiperazine (BZP), methylenedioxybenzylpiperazine (MDBP), methoxyphenylpiperazine (MeOPP), methylbenzylpiperazine (MBZP), or Trifluoromethylphenylpiperazine (TFMPP).

pharmacology

The m-CPP is a metabolite of two new generation of antidepressants from the class of dual-serotonergic agents, which can also be obtained synthetically. In the human body, the piperazine derivatives trazodone and nefazodone , which are already chemically related to meta-chlorophenylpiperazine, are also metabolized (metabolized) to this. The drug trazodone is used as an antidepressant of the DSA class and has also been marketed in Germany for several years. The antidepressant containing nefazodone was withdrawn from the market in 2003.

The panic and anxiety inducing effect of m-CPP is medically well documented. Overstimulation (upregulation) of the 5-HT2C receptor is usually associated with a (sometimes extremely violent) depressive mood.

At the end of 2008, tablets with the ingredient m-CPP were confiscated as ecstasy .

effect

m-CPP is a serotonin receptor agonist and regulates the 5-HT receptors, which have an important influence on the psychological state of a person and the interplay of which influences depression and anxiety.

Legal position

  • Switzerland : With the entry into force of the revised Narcotics Ordinance by Swissmedic on December 1, 2010, m-CPP will be subject to the Narcotics Act and will therefore be illegal from that point on. Importation, possession, distribution etc. are punished according to the Narcotics Act.

literature

  • Hartmut Göbel: The headaches: causes, mechanisms, diagnostics and therapy in practice , from page 222 ISBN 3-540-03080-8
  • Rene S. Kahn, Scott Wetzler: m-Chlorophenylpiperazine as a probe of serotonin function . In: Biological Psychiatry . tape 30 , no. 11 , 1991, p. 1139-1166 , doi : 10.1016 / 0006-3223 (91) 90184-N (review).
  • Michael B. Gatch: Discriminative stimulus effects of m-chlorophenylpiperazine as a model of the role of serotonin receptors in anxiety . In: Life Sciences . tape 73 , no. 11 , 2003, p. 1347-1367 , doi : 10.1016 / S0024-3205 (03) 00422-3 (review).
  • RS Kahn, S. Wetzler, GM Asnis, MA Kling, RF Suckow, HM van Praag: Effects of m-chlorophenylpiperazine in normal subjects: a dose-response study . In: Psychopharmacology . tape 100 , no. 3 , 1990, p. 339-344 , doi : 10.1007 / BF02244603 .

Individual evidence

  1. ↑ a b Registration dossier on 1- (m-chlorophenyl) piperazine ( GHS section ) at the European Chemicals Agency (ECHA), accessed on October 31, 2016.
  2. ^ Neera Ghaziuddin et al .: Central Serotonergic Effects of m-Chlorophenylpiperazine (mCPP) among Normal Control Adolescents. In: Neuropsychopharmacology . Volume 28, 2003, pp. 133-139. doi: 10.1038 / sj.npp.1300006 . PMID 12496949 .
  3. ↑ Text of the Swissmedic Narcotics Ordinance, which came into force on December 1, 2010, as PDF .
  4. ↑ Text of the Swiss Narcotics Act as PDF. Relevant criminal provisions: Art. 19 and following. .

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