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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:08 UTC
Update Date2017-12-07 18:55:50 UTC
HMDB IDHMDB0061135
Secondary Accession Numbers
  • HMDB61135
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
Synonyms
ValueSource
Norchlorpromazine perchlorate, ion(1+)MeSH
N-MonodesmethylchlorpromazineMeSH
Norchlorpromazine, ion(1+)MeSH
Norchlorpromazine maleateMeSH
N-DesmethylchlorpromazineMeSH
Norchlorpromazine hydrochlorideMeSH
Norchlorpromazine monomaleateMeSH
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 KeyYHFXGBOUSIKGMZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Tertiary aliphatic/aromatic amine
  • Aryl thioether
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Para-thiazine
  • Tertiary amine
  • Thioether
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 g/LALOGPS
logP4.27ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.46 m³·mol⁻¹ChemAxon
Polarizability32.71 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6190000000-7064bdabc610ca9935f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-1059000000-f303e6242cff85b0f9dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6094000000-7b134b7d8070a91bd7acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9140000000-39465a7f6fe6a1a2470aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-6c714d0b3a8c7f6d1fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgl-0955000000-d24dce6613357abb0022View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2190000000-1220ae1f2fdd7f153d92View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      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