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
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
| 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P28335 Gene ID: 3358.0 Gene Symbol: HTR2C Target Organism: Homo sapiens (Human) |
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Target ID: P41595 Gene ID: 3357.0 Gene Symbol: HTR2B Target Organism: Homo sapiens (Human) |
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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 |
|---|---|---|
| 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 |
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
by
admin
on
Edited
Fri Jun 25 20:34:46 UTC 2021
by
admin
on
Fri Jun 25 20:34:46 UTC 2021
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| Record UNII |
REY0CNO998
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| Record Status |
Validated (UNII)
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| Record Version |
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6640-24-0
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229-654-7
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SUB87155
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6640-24-0
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REY0CNO998
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META-CHLOROPHENYLPIPERAZINE
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1355
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DB12110
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE ACTIVE | |||
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PARENT -> METABOLITE ACTIVE | |||
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METABOLITE -> PARENT | |||
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PARENT -> METABOLITE ACTIVE | |||
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PARENT -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
