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Record Information
Version3.6
Creation Date2013-07-22 19:50:08 UTC
Update Date2016-02-11 08:19:01 UTC
HMDB IDHMDB61135
Secondary Accession NumbersNone
Metabolite Identification
Common NameDemonomethylchlorpromazine
DescriptionDemonomethylchlorpromazine is a metabolite of chlorpromazine. Chlorpromazine (as chlorpromazine hydrochloride, abbreviated CPZ; marketed in the United States as Thorazine and elsewhere as Largactil) is a typical antipsychotic. First synthesized on December 11, 1950, chlorpromazine was the first drug developed with specific antipsychotic action, and would serve as the prototype for the phenothiazine class of drugs, which later grew to comprise several other agents. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H17ClN2S
Average Molecular Weight304.838
Monoisotopic Molecular Weight304.080096951
IUPAC Name[3-(2-chloro-10H-phenothiazin-10-yl)propyl](methyl)amine
Traditional Name[3-(2-chlorophenothiazin-10-yl)propyl](methyl)amine
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2
InChI Identifier
InChI=1S/C16H17ClN2S/c1-18-9-4-10-19-13-5-2-3-6-15(13)20-16-8-7-12(17)11-14(16)19/h2-3,5-8,11,18H,4,9-10H2,1H3
InChI KeyInChIKey=YHFXGBOUSIKGMZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Para-thiazine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0051 mg/mLALOGPS
logP4.27ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.46 m3·mol-1ChemAxon
Polarizability32.71 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00825
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61135
Metagene LinkHMDB61135
METLIN IDNot Available
PubChem Compound62875
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available