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Details

Stereochemistry ACHIRAL
Molecular Formula C10H13ClN2
Molecular Weight 196.6769
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of M-CHLOROPHENYLPIPERAZINE

SMILES

c1cc(cc(c1)N2CCNCC2)Cl

InChI

InChIKey=VHFVKMTVMIZMIK-UHFFFAOYSA-N
InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2

HIDE SMILES / InChI

Molecular Formula C10H13ClN2
Molecular Weight 196.6769
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

m-Chlorophenylpiperazine (meta-chlorophenylpiperazine or mCPP) is a psychoactive substance, which is illegal in many countries but can be found on the black market. It induces endocrine, neurological and psychiatric effects. mCPP is a partial agonist at the 5-HT2C receptor but antagonized the 5-HT2B and 5-HT3 receptors. mCPP is also an active metabolite of the drug trazodone, which is used as an effective antidepressant drug with a broad therapeutic spectrum, including anxiolytic efficacy. It is known, that mCPP induces migraine attacks and that the decrease of food intake induced by the mCPP depends on its ability to act as a serotonin agonist is a brain.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28335
Gene ID: 3358.0
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
Target ID: P41595
Gene ID: 3357.0
Gene Symbol: HTR2B
Target Organism: Homo sapiens (Human)
Target ID: P08908
Gene ID: 3350.0
Gene Symbol: HTR1A
Target Organism: Homo sapiens (Human)
61.4 nM [IC50]
6.65 null [pEC50]
7.09 null [pEC50]
7.2 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inhibition of K(+)-evoked release of rat striatal 5-hydroxytryptamine by an atypical antidepressant: trazodone.
2001
SB-243213; a selective 5-HT2C receptor inverse agonist with improved anxiolytic profile: lack of tolerance and withdrawal anxiety.
2001 Aug
Pedophilia is accompanied by increased plasma concentrations of catecholamines, in particular epinephrine.
2001 Aug 5
m-CPP hypolocomotion is selectively antagonized by compounds with high affinity for 5-HT(2C) receptors but not 5-HT(2A) or 5-HT(2B) receptors.
2001 Dec
The effect of olanzapine treatment on m-chlorophenylpiperazine-induced hormone release in schizophrenia.
2001 Dec
Altered responsiveness to 5-HT at the crayfish neuromuscular junction due to chronic p-CPA and m-CPP treatment.
2001 Oct 19
Mapping of brain activation in response to pharmacological agents using fMRI in the rat.
2001 Sep
Association of serotonin and cortisol indices with childhood abuse in bulimia nervosa.
2001 Sep
The nature of the acetylcholine and 5-hydroxytryptamine receptors in buccal smooth muscle of the pest slug Deroceras reticulatum.
2002 Apr
Alteration in 5-hydroxytryptamine agonist-induced behaviour following a corticosterone implant in adult rats.
2002 Apr
Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes.
2002 Apr
5-HT(2C) receptor activation by m-chlorophenylpiperazine detected in humans with fMRI.
2002 Aug 27
Involvement of 5-HT(2A/2B/2C) receptors on memory formation: simple agonism, antagonism, or inverse agonism?
2002 Dec
Antidepressants reduce phosphoinositide-specific phospholipase C (PI-PLC) activity and the mRNA and protein expression of selective PLC beta 1 isozyme in rat brain.
2002 Dec
Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies.
2002 Dec
Cognitive performance of MDMA-treated rhesus monkeys: sensitivity to serotonergic challenge.
2002 Dec
Synthesis and pharmacological evaluation of new arylpiperazines. 3-[4-[4-(3-chlorophenyl)-1-piperazinyl]butyl]-quinazolidin-4-one - a dual serotonin 5-HT(1A)/5-HT(2A) receptor ligand with an anxiolytic-like activity.
2002 Dec
Perturbations of plasma cortisol and DHEA-S following discontinuation of cocaine use in cocaine addicts.
2002 Jan-Feb
Therapeutic and adverse actions of serotonin transporter substrates.
2002 Jul
Central administration of mCPP, a serotonin 5-HT(2B/2C) agonist, decreases water intake in rats.
2002 Jul
Saccadic peak velocity and EEG as end-points for a serotonergic challenge test.
2002 Mar
The atypical 5-HT2 receptor mediating tachycardia in pithed rats: pharmacological correlation with the 5-HT2A receptor subtype.
2002 Mar
Allelic variants of the serotonin(2C) receptor and neuroendocrinological responses to the serotonin(2C) receptor agonist m-chlorophenylpiperazine in healthy male volunteers.
2002 Nov
5-HT2C receptor mediation of unconditioned escape behaviour in the unstable elevated exposed plus maze.
2002 Nov
Sleep-wake effects of meta-chlorophenyl piperazine and mianserin in the behaviorally depressed rat.
2002 Nov 22
Effects of GABA(A) compounds on mCPP drug discrimination in rats.
2002 Oct 18
5-HT2C receptor agonists as potential drugs for the treatment of obesity.
2003
Serotonin induces tonic firing in layer V pyramidal neurons of rat prefrontal cortex during postnatal development.
2003 Apr 15
Effects of m-CPP in altering neuronal function: blocking depolarization in invertebrate motor and sensory neurons but exciting rat dorsal horn neurons.
2003 Apr 18
MDMA exposure alters cognitive and electrophysiological sensitivity to rapid tryptophan depletion in rhesus monkeys.
2003 Aug
Regulation of septo-hippocampal activity by 5-hydroxytryptamine(2C) receptors.
2003 Aug
Discriminative stimulus effects of m-chlorophenylpiperazine as a model of the role of serotonin receptors in anxiety.
2003 Aug 1
Central 5-HT2B/2C and 5-HT3 receptor stimulation decreases salt intake in sodium-depleted rats.
2003 Aug 15
Effect of repeated administration of dexfenfluramine on feeding and brain Fos in mice.
2003 Feb
Differential regulation of somatodendritic and nerve terminal dopamine release by serotonergic innervation of substantia nigra.
2003 Feb
Induction of c-Fos expression in specific areas of the fear circuitry in rat forebrain by anxiogenic drugs.
2003 Feb 15
5-HT1B receptor knockout mice show a compensatory reduction in 5-HT2C receptor function.
2003 Jan
Pharmacological characterization of 5-HT(1B) receptor-mediated inhibition of local excitatory synaptic transmission in the CA1 region of rat hippocampus.
2003 Jan
Central serotonergic effects of m-chlorophenylpiperazine (mCPP) among normal control adolescents.
2003 Jan
Neuroendocrine response to the serotonin agonist M-chlorophenylpiperazine in women with menstrual status migrainosus.
2003 Jul
Serotonin in the dorsal periaqueductal gray modulates inhibitory avoidance and one-way escape behaviors in the elevated T-maze.
2003 Jul 25
Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry.
2003 Jun
Effects of single and repeated electroconvulsive shock on the social and agonistic behaviour of resident rats.
2003 Jun
m-CPP-induced self-grooming is mediated by 5-HT2C receptors.
2003 Jun 16
The glycine transporter-1 inhibitors NFPS and Org 24461: a pharmacological study.
2003 Mar
Reduced social interaction following 3,4-methylenedioxymethamphetamine is not associated with enhanced 5-HT 2C receptor responsivity.
2003 Mar
Neurogenic dural protein extravasation induced by meta-chlorophenylpiperazine (mCPP) involves nitric oxide and 5-HT2B receptor activation.
2003 Mar
Experimental anxiety and antiepileptics: the effects of valproate and vigabatrin in the mirrored chamber test.
2003 May
Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy.
2003 Sep
A PET study after treatment with an anxiety-provoking agent, m-chlorophenyl-piperazine, in conscious rhesus monkeys.
2003 Sep
Patents

Sample Use Guides

Eight female and six male healthy volunteers were included in a randomized, double-blind, double-dummy, three-way crossover design of single-dose intravenous (0.1 mg/kg), oral (0.5 mg/kg), and placebo treatment, with 24-hour follow-up. meta-Chlorophenylpiperazine (mCPP) showed a large variability in clearance (11-92 mL/hr) and bioavailability (14-108%).
Route of Administration: Other
In Vitro Use Guide
meta-Chlorophenylpiperazine (mCPP) showed relatively high affinity at brain 5HT3 receptors (IC50 = 61.4 nM), it did not activate the von Bezold-Jarisch reflex; instead, mCPP potently antagonized serotonin-induced bradycardia. Thus, mCPP acts as an antagonist at 5HT3 receptors in the periphery
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:34:46 UTC 2021
Edited
by admin
on Fri Jun 25 20:34:46 UTC 2021
Record UNII
REY0CNO998
Record Status Validated (UNII)
Record Version
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Name Type Language
M-CHLOROPHENYLPIPERAZINE
Systematic Name English
M-CPP
Common Name English
3-CHLOROPHENYLPIPERAZINE
Systematic Name English
MCPP
Common Name English
3CPP
Common Name English
J227.960F
Code English
META-CHLOROPHENYLPIPERAZINE
Systematic Name English
LOROPHYN
Brand Name English
1-(3-CHLOROPHENYL)PIPERAZINE
Systematic Name English
NSC-49307
Code English
META-CHLOROPHENYL-PIPERAZINE
Systematic Name English
3-CHLOROPHENYL PIPERAZINE
Systematic Name English
Code System Code Type Description
CAS
6640-24-0
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
229-654-7
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
EVMPD
SUB87155
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
EPA CompTox
6640-24-0
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
FDA UNII
REY0CNO998
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
WIKIPEDIA
META-CHLOROPHENYLPIPERAZINE
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
PUBCHEM
1355
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
DRUG BANK
DB12110
Created by admin on Fri Jun 25 20:34:46 UTC 2021 , Edited by admin on Fri Jun 25 20:34:46 UTC 2021
PRIMARY
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