Carphenazine (CHEM002329)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:14 UTC
Update Date2026-05-14 16:56:29 UTC
Accession NumberCHEM002329
Identification
Common NameCarphenazine
ClassSmall Molecule
DescriptionCarphenazine is only found in individuals that have used or taken this drug. It is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.A yellow, powdered, phenothiazine antipsychotic agent used in the treatment of acute or chronic schizophrenia. The term phenothiazines is used to describe the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as akathisia, tardive dyskinesia and extrapyramidal symptoms. Carphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antipsychotic Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl)-1-propanoneChEBI
CarfenazinaChEBI
CarfenazineChEBI
CarfenazinumChEBI
CarphenazinHMDB
Chemical FormulaC23H29N3O2S
Average Molecular Mass411.560 g/mol
Monoisotopic Mass411.198 g/mol
CAS Registry Number2622-30-2
IUPAC Name1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
Traditional Namecarfenazina
SMILESCCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1
InChI IdentifierInChI=1S/C23H29N3O2S/c1-2-21(28)18-7-8-23-20(17-18)26(19-5-3-4-6-22(19)29-23)14-13-24-9-11-25(12-10-24)15-16-27/h3-8,17,27H,2,9-16H2,1H3
InChI KeyDYCNETKPCXPXNW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Aryl alkyl ketone
  • Aryl ketone
  • N-alkylpiperazine
  • Para-thiazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • 1,2-aminoalcohol
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Alkanolamine
  • Azacycle
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point175-177°C
Boiling PointNot Available
Solubility9.05e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP2.84ALOGPS
logP3.29ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)15.56ChemAxon
pKa (Strongest Basic)8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.02 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.46 m³·mol⁻¹ChemAxon
Polarizability47.25 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-1249000000-8269c1aea27b4519caf5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-4489800000-a2dc84d530af6c491e7eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0326900000-6e5ae095bf0ef6084542Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu0-2792000000-1cff5a929ddf220c741bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bu1-5932000000-98b40f4a2cdbae56d3abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0005900000-6bb5170e920dc2485681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udm-0196100000-4cbb6b3fa5eccbfc7980Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k97-9653000000-000631b921931d7be9baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-94a2b7e7b061d0929453Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0190400000-27679b67f9c21cea78daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022a-8931000000-36b009ad5cd7ac7aec2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-474df7b273d6c5e26ef6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0038900000-91fbc50a2f95f1bd7526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2192000000-96e0f1beaa722034f19aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityA yellow, powdered, phenothiazine antipsychotic agent used in the treatment of acute or chronic schizophrenia. The term "phenothiazines" is used to describe the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as akathisia, tardive dyskinesia and extrapyramidal symptoms. Carphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0015172
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarphenazine
Chemspider ID21865853
ChEBI ID51235
PubChem Compound ID25137957
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Tislow, R.F., Bruce, W.F. and Page, J.A.; US. Patent 3,023,146; February 27,1962; assigned to American Home Products Corporation.
Sherlock, M.H. and Sperber, N.; US. Patent 2,985,654; May 23, 1961; assigned to Schering
Corporation.

MSDSNot Available
General ReferencesNot Available