Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13ClN2.ClH |
| Molecular Weight | 233.138 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.ClC1=CC=CC(=C1)N2CCNCC2
InChI
InChIKey=MHXPYWFZULXYHT-UHFFFAOYSA-N
InChI=1S/C10H13ClN2.ClH/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13;/h1-3,8,12H,4-7H2;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) |
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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 |
|---|---|---|
| High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action. | 1999 May |
|
| Inhibition of K(+)-evoked release of rat striatal 5-hydroxytryptamine by an atypical antidepressant: trazodone. | 2001 |
|
| Effects of serotonin and serotonin analogs on posture and agonistic behavior in crayfish. | 2001 Dec |
|
| Neuroendocrine and behavioral responses to mCPP in Obsessive-Compulsive Disorder. | 2001 Feb |
|
| Lower baseline plasma cortisol and prolactin together with increased body temperature and higher mCPP-induced cortisol responses in men with pedophilia. | 2001 Jan |
|
| 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 |
|
| The serotonergic 5-HT(2C) agonist m-chlorophenylpiperazine increases weight-supported locomotion without development of tolerance in rats with spinal transections. | 2001 Jun |
|
| 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 |
|
| Dissociation of systemic and hippocampal modulation of rat locomotor activity by 5-HT(2C) receptors. | 2001 May |
|
| Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man. | 2001 Nov |
|
| Mapping of brain activation in response to pharmacological agents using fMRI in the rat. | 2001 Sep |
|
| The nature of the acetylcholine and 5-hydroxytryptamine receptors in buccal smooth muscle of the pest slug Deroceras reticulatum. | 2002 Apr |
|
| Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes. | 2002 Apr |
|
| Effects of fenfluramine, m-CPP and triazolam on repeated-acquisition in squirrel monkeys before and after neurotoxic MDMA administration. | 2002 Feb |
|
| Antinociceptive role of 5-HT1A receptors in rat spinal cord. | 2002 May |
|
| 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 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 |
|
| 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 |
|
| Effect of repeated administration of dexfenfluramine on feeding and brain Fos in mice. | 2003 Feb |
|
| 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 |
|
| 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 |
|
| 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
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| Record UNII |
7IM2GS7ILV
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| Record Status |
Validated (UNII)
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