Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13ClN2.2ClH |
| Molecular Weight | 269.599 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.ClC1=CC(=CC=C1)N2CCNCC2
InChI
InChIKey=OSZCTRWSGNWWBL-UHFFFAOYSA-N
InChI=1S/C10H13ClN2.2ClH/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13;;/h1-3,8,12H,4-7H2;2*1H
| Molecular Formula | C10H13ClN2 |
| Molecular Weight | 196.677 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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) |
|||
Target ID: CHEMBL2094132 |
61.4 nM [IC50] | ||
Target ID: CHEMBL224 |
6.65 null [pEC50] | ||
Target ID: CHEMBL225 |
7.09 null [pEC50] | ||
Target ID: CHEMBL1833 |
7.2 null [pEC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy. | 2003-09 |
|
| A PET study after treatment with an anxiety-provoking agent, m-chlorophenyl-piperazine, in conscious rhesus monkeys. | 2003-09 |
|
| Central 5-HT2B/2C and 5-HT3 receptor stimulation decreases salt intake in sodium-depleted rats. | 2003-08-15 |
|
| Discriminative stimulus effects of m-chlorophenylpiperazine as a model of the role of serotonin receptors in anxiety. | 2003-08-01 |
|
| MDMA exposure alters cognitive and electrophysiological sensitivity to rapid tryptophan depletion in rhesus monkeys. | 2003-08 |
|
| Regulation of septo-hippocampal activity by 5-hydroxytryptamine(2C) receptors. | 2003-08 |
|
| Serotonin in the dorsal periaqueductal gray modulates inhibitory avoidance and one-way escape behaviors in the elevated T-maze. | 2003-07-25 |
|
| Neuroendocrine response to the serotonin agonist M-chlorophenylpiperazine in women with menstrual status migrainosus. | 2003-07 |
|
| m-CPP-induced self-grooming is mediated by 5-HT2C receptors. | 2003-06-16 |
|
| Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry. | 2003-06 |
|
| Effects of single and repeated electroconvulsive shock on the social and agonistic behaviour of resident rats. | 2003-06 |
|
| Experimental anxiety and antiepileptics: the effects of valproate and vigabatrin in the mirrored chamber test. | 2003-05 |
|
| Effects of m-CPP in altering neuronal function: blocking depolarization in invertebrate motor and sensory neurons but exciting rat dorsal horn neurons. | 2003-04-18 |
|
| Serotonin induces tonic firing in layer V pyramidal neurons of rat prefrontal cortex during postnatal development. | 2003-04-15 |
|
| The glycine transporter-1 inhibitors NFPS and Org 24461: a pharmacological study. | 2003-03 |
|
| Reduced social interaction following 3,4-methylenedioxymethamphetamine is not associated with enhanced 5-HT 2C receptor responsivity. | 2003-03 |
|
| Neurogenic dural protein extravasation induced by meta-chlorophenylpiperazine (mCPP) involves nitric oxide and 5-HT2B receptor activation. | 2003-03 |
|
| Induction of c-Fos expression in specific areas of the fear circuitry in rat forebrain by anxiogenic drugs. | 2003-02-15 |
|
| Effect of repeated administration of dexfenfluramine on feeding and brain Fos in mice. | 2003-02 |
|
| Differential regulation of somatodendritic and nerve terminal dopamine release by serotonergic innervation of substantia nigra. | 2003-02 |
|
| 5-HT1B receptor knockout mice show a compensatory reduction in 5-HT2C receptor function. | 2003-01 |
|
| Pharmacological characterization of 5-HT(1B) receptor-mediated inhibition of local excitatory synaptic transmission in the CA1 region of rat hippocampus. | 2003-01 |
|
| Central serotonergic effects of m-chlorophenylpiperazine (mCPP) among normal control adolescents. | 2003-01 |
|
| 5-HT2C receptor agonists as potential drugs for the treatment of obesity. | 2003 |
|
| Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression. | 2002-12-15 |
|
| Involvement of 5-HT(2A/2B/2C) receptors on memory formation: simple agonism, antagonism, or inverse agonism? | 2002-12 |
|
| Antidepressants reduce phosphoinositide-specific phospholipase C (PI-PLC) activity and the mRNA and protein expression of selective PLC beta 1 isozyme in rat brain. | 2002-12 |
|
| Serotonergic dysregulation in bipolar disorders: a literature review of serotonergic challenge studies. | 2002-12 |
|
| Cognitive performance of MDMA-treated rhesus monkeys: sensitivity to serotonergic challenge. | 2002-12 |
|
| 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. | 2002-12 |
|
| Sleep-wake effects of meta-chlorophenyl piperazine and mianserin in the behaviorally depressed rat. | 2002-11-22 |
|
| Allelic variants of the serotonin(2C) receptor and neuroendocrinological responses to the serotonin(2C) receptor agonist m-chlorophenylpiperazine in healthy male volunteers. | 2002-11 |
|
| In vitro identification of metabolic pathways and cytochrome P450 enzymes involved in the metabolism of etoperidone. | 2002-11 |
|
| The effects of gender and gonadal steroids on the neuroendocrine and temperature response to m-chlorophenylpiperazine in leuprolide-induced hypogonadism in women and men. | 2002-11 |
|
| 5-HT2C receptor mediation of unconditioned escape behaviour in the unstable elevated exposed plus maze. | 2002-11 |
|
| 2'-NH(2)-MPTP [1-methyl-4-(2'-aminophenyl)-1,2,3,6-tetrahydropyridine] depletes serotonin and norepinephrine in rats: a comparison with 2'-CH(3)-MPTP [1-methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine]. | 2002-11 |
|
| Effects of GABA(A) compounds on mCPP drug discrimination in rats. | 2002-10-18 |
|
| mCPP-induced hypophagia in rats is unaffected by the profile of dietary unsaturated fatty acids. | 2002-10 |
|
| 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. | 2002-09 |
|
| 5-HT(2C) receptor activation by m-chlorophenylpiperazine detected in humans with fMRI. | 2002-08-27 |
|
| The effects of serotonin agonists on the hypothalamic regulation of sexual receptivity in Syrian hamsters. | 2002-08 |
|
| Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats. | 2002-08 |
|
| Relationship between plasma concentrations of trazodone and its active metabolite, m-chlorophenylpiperazine, and its clinical effect in depressed patients. | 2002-08 |
|
| Therapeutic and adverse actions of serotonin transporter substrates. | 2002-07 |
|
| Blunted prefrontal cortical 18fluorodeoxyglucose positron emission tomography response to meta-chlorophenylpiperazine in impulsive aggression. | 2002-07 |
|
| Central administration of mCPP, a serotonin 5-HT(2B/2C) agonist, decreases water intake in rats. | 2002-07 |
|
| Ritanserin antagonism of m-chlorophenylpiperazine effects in neuroleptic-free schizophrenics patients: support for serotonin-2 receptor modulation of schizophrenia symptoms. | 2002-06 |
|
| Antinociceptive role of 5-HT1A receptors in rat spinal cord. | 2002-05 |
|
| Ethopharmacological analysis of the unstable elevated exposed plus maze, a novel model of extreme anxiety: predictive validity and sensitivity to anxiogenic agents. | 2002-05 |
|
| Saccadic peak velocity and EEG as end-points for a serotonergic challenge test. | 2002-03 |
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
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
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admin
on
Edited
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| Record UNII |
MY02G3EAXQ
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| Record Status |
Validated (UNII)
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| Record Version |
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