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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
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.
2000 Dec 5
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
2000 Feb
Tryptophan hydroxylase gene and major psychoses.
2001 Aug 5
Pedophilia is accompanied by increased plasma concentrations of catecholamines, in particular epinephrine.
2001 Aug 5
Anxiety-like effects induced by acute fluoxetine, sertraline or m-CPP treatment are reversed by pretreatment with the 5-HT2C receptor antagonist SB-242084 but not the 5-HT1A receptor antagonist WAY-100635.
2001 Dec
Increased m-CPP-induced oral dyskinesia after lesion of serotonergic neurons.
2001 Feb
Implications of impulsive and affective symptoms for serotonin function in bulimia nervosa.
2001 Jan
Lower baseline plasma cortisol and prolactin together with increased body temperature and higher mCPP-induced cortisol responses in men with pedophilia.
2001 Jan
Effect of a low tryptophan diet on the prolactin responses to the 5-HT2A agonist DOI in the rat.
2001 Jul
Altered response to meta-chlorophenylpiperazine in anorexia nervosa: support for a persistent alteration of serotonin activity after short-term weight restoration.
2001 Jul
Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists.
2001 Jul-Aug
Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats.
2001 Mar
Effects of genetic polymorphism of CYP1A2 inducibility on the steady-state plasma concentrations of trazodone and its active metabolite m-chlorophenylpiperazine in depressed Japanese patients.
2001 May
Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man.
2001 Nov
Altered responsiveness to 5-HT at the crayfish neuromuscular junction due to chronic p-CPA and m-CPP treatment.
2001 Oct 19
Association of serotonin and cortisol indices with childhood abuse in bulimia nervosa.
2001 Sep
Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes.
2002 Apr
The effects of serotonin agonists on the hypothalamic regulation of sexual receptivity in Syrian hamsters.
2002 Aug
Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats.
2002 Aug
Relationship between plasma concentrations of trazodone and its active metabolite, m-chlorophenylpiperazine, and its clinical effect in depressed patients.
2002 Aug
5-HT(2C) receptor activation by m-chlorophenylpiperazine detected in humans with fMRI.
2002 Aug 27
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
Comparison of the potency of MDL 100,907 and SB 242084 in blocking the serotonin (5-HT)(2) receptor agonist-induced increases in rat serum corticosterone concentrations: evidence for 5-HT(2A) receptor mediation of the HPA axis.
2002 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
Antinociceptive role of 5-HT1A receptors in rat spinal cord.
2002 May
In vitro identification of metabolic pathways and cytochrome P450 enzymes involved in the metabolism of etoperidone.
2002 Nov
Sleep-wake effects of meta-chlorophenyl piperazine and mianserin in the behaviorally depressed rat.
2002 Nov 22
mCPP-induced hypophagia in rats is unaffected by the profile of dietary unsaturated fatty acids.
2002 Oct
Effects of GABA(A) compounds on mCPP drug discrimination in rats.
2002 Oct 18
p-Methylthioamphetamine and 1-(m-chlorophenyl)piperazine, two non-neurotoxic 5-HT releasers in vivo, differ from neurotoxic amphetamine derivatives in their mode of action at 5-HT nerve endings in vitro.
2002 Sep
MDMA exposure alters cognitive and electrophysiological sensitivity to rapid tryptophan depletion in rhesus monkeys.
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
m-CPP-induced self-grooming is mediated by 5-HT2C receptors.
2003 Jun 16
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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