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) |
|||
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 |
|---|---|---|
| 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 |
|
| 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 |
|
| Effects of serotonin and serotonin analogs on posture and agonistic behavior in crayfish. | 2001 Dec |
|
| The 5-HT2C/2B receptor agonist m-chlorophenylpiperazine (mCPP) inhibits 2-deoxy-D-glucose (2-DG)-induced hyperphagia in rats. | 2001 Dec |
|
| The effect of olanzapine treatment on m-chlorophenylpiperazine-induced hormone release in schizophrenia. | 2001 Dec |
|
| Psychomotor slowing, neuroendocrine responses, and behavioral changes after oral administration of meta-chlorophenylpiperazine in normal volunteers. | 2001 Dec 31 |
|
| Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man. | 2001 Nov |
|
| The nature of the acetylcholine and 5-hydroxytryptamine receptors in buccal smooth muscle of the pest slug Deroceras reticulatum. | 2002 Apr |
|
| Serotonin 2C receptor agonists and the behavioural satiety sequence in mice. | 2002 Apr |
|
| Human CYP3A4 and the metabolism of nefazodone and hydroxynefazodone by human liver microsomes and heterologously expressed enzymes. | 2002 Apr |
|
| Altered prolactin response to M-chlorophenylpiperazine in monkeys previously treated with 3,4-methylenedioxymethamphetamine (MDMA) or fenfluramine. | 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 |
|
| 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 |
|
| Neuroendocrine response to meta-chlorophenylpiperazine and ipsapirone in relation to anxiety and aggression. | 2002 Dec 15 |
|
| Effects of fenfluramine, m-CPP and triazolam on repeated-acquisition in squirrel monkeys before and after neurotoxic MDMA administration. | 2002 Feb |
|
| 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 |
|
| Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors. | 2002 Jan 21 |
|
| 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 |
|
| Blunted prefrontal cortical 18fluorodeoxyglucose positron emission tomography response to meta-chlorophenylpiperazine in impulsive aggression. | 2002 Jul |
|
| Central administration of mCPP, a serotonin 5-HT(2B/2C) agonist, decreases water intake in rats. | 2002 Jul |
|
| Ritanserin antagonism of m-chlorophenylpiperazine effects in neuroleptic-free schizophrenics patients: support for serotonin-2 receptor modulation of schizophrenia symptoms. | 2002 Jun |
|
| 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 |
|
| Antinociceptive role of 5-HT1A receptors in rat spinal cord. | 2002 May |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 Dec 15 15:20:07 GMT 2023
by
admin
on
Fri Dec 15 15:20:07 GMT 2023
|
| Record UNII |
7IM2GS7ILV
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
134746
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
65369-76-8
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
NON-SPECIFIC STOICHIOMETRY | |||
|
DBSALT002641
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
235-976-9
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
265-718-0
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
ALTERNATIVE | |||
|
13078-15-4
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
25681
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
7IM2GS7ILV
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY | |||
|
DTXSID40896823
Created by
admin on Fri Dec 15 15:20:07 GMT 2023 , Edited by admin on Fri Dec 15 15:20:07 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> SALT/SOLVATE |
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ACTIVE MOIETY |
|