Basic information
- CAS
6640-24-0- Standard SMILES
Clc1cccc(N2CCNCC2)c1- InChIKey
VHFVKMTVMIZMIK-UHFFFAOYSA-N- Molecular formula
- C10H13ClN2
- Average molar mass
- 196.67 g/mol
- Monoisotopic mass
- 196.0767261
Overview
1-(3-chlorophenyl)piperazine is a N-arylpiperazine that is piperazine carrying a 3-chlorophenyl substituent at position 1. It is a metabolite of the antidepressant drug trazodone. It has a role as a xenobiotic, a serotonergic agonist, a drug metabolite and an environmental contaminant. It is a N-arylpiperazine and a member of monochlorobenzenes.
Names & identifiers
- Preferred name
- 1-(3-Chlorophenyl)piperazine
- IUPAC
- 1-(3-chlorophenyl)piperazine
- English name
- 1-(3-Chlorphenyl)piperazine
- Molecular formula
- C10H13ClN2
- Molecular weight
- 196.68
Names & synonyms
1-(3-Chlorophenyl)piperazine6640-24-0m-Chlorophenylpiperazinem-CPP1-(m-Chlorophenyl)piperazine3-chlorophenylpiperazineDTXSID9045138REY0CNO998NSC-49307J227.960FDTXCID7025138CHEBI:10588
Show more names
MCPPCHLOROPHENYLPIPERAZINENSC 49307AKOS BBS-00003580TIMTEC-BB SBB003579RARECHEM AH CK 00711,3ChlorofenylPiperazine
1-3-CPPRefChem:74314dihydrochloro phenyl piperazine229-654-73-Chlorophenyl piperazine1-(3-Chlorophenyl) piperazineCHEMBL478m-chlorophenylpiperazine (m-CPP)
Database identifiers
- CAS
6640-24-0- PubChem CID
- 1355
- DTXSID
DTXSID9045138- ChEMBL
CHEMBL478- ChEBI
CHEBI:10588- UNII
- REY0CNO998
- EC Number
- 229-654-7
- Nikkaji
- J227.960F
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 15.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 157
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Trazodone
LogP2.11
Human DrugsPharmaceuticals
Collision Cross Section
141.91 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
144.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 210 · 210-214°C
- Boiling point
- 105 °C · 105 °C
- Density
- 1.193 · 1.193
- refractive index
- 1 · 1,598-1,600
- storage temp.
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly), Methanol (Sparingly)
- form
- Oil
- pka
- 8.85 · 8.85±0.10(Predicted)
- color
- Colourless to Orange
- LogP
- 2.468 · 2.468
- CAS DataBase Reference
- 6640 · 6640-24-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 CNO998 · REY0CNO998
- Symbol(GHS)
- 9 · GHS09
- Hazard statements
- 411 · H411
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37/39-36
- HazardClass
- IRRITANT
- HS Code
- 29339900 · 29339900
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.7% (1 of 59) of reports.
Warning
H302 (71.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 59 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 05-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/11716
Hazard Classes and CategoriesAcute Tox. 4 (71.2%)
Safety data
- hs_code
- 29339900
- risk_code
- 36/37/38
- Symbol(GHS)
- GHS09
- hazard_code
- Xi
- safety_code
- 26-36/37/39-36
- hazard_class
- IRRITANT
- Hazard statements
- H411
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
Metabolism/Metabolites1-(3-Chlorophenyl)piperazine has known human metabolites that include 2-chloro-4-(piperazin-1-yl)phenol.
MeSH Pharmacological ClassificationEndogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesIt is noteworthy that 1-(3-Chlorphenyl)piperazine (m-CPP), resulting from N-dealkylation of Trazodone, is a major circulating metabolite in humans common to several antidepressants including Trazodone, Nefazodone, and Etoperidone (1,2,3). The metabolite m-CPP is of significant interest because it has 5-HT2C agonistic and 5-HT2A antagonistic properties. It has also been suggested that m-CPP may contribute to the antidepressant efficacy of Trazodone.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A N-arylpiperazine that is piperazine carrying a 3-chlorophenyl substituent at position 1. It is a metabolite of the antidepressant drug trazodone.
Related reactions
179 records
Compound notes
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