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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:05 UTC
Update Date2019-07-23 07:15:50 UTC
HMDB IDHMDB0061134
Secondary Accession Numbers
  • HMDB61134
Metabolite Identification
Common NameDedimethylchlorpromazine
DescriptionDedimethylchlorpromazine 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
Data?1563866150
Synonyms
ValueSource
Didemethylchlorpromazine monomaleateHMDB
2-Chloro-10-(3-aminopropyl)phenothiazineHMDB
CPZSLHMDB
Didemethylchlorpromazine monohydrochlorideHMDB
Didemethylchlorpromazine perchlorate ion (1+)HMDB
gamma-(2-Chlorophenothiazinyl-10)-propylamineHMDB
Didemethylchlorpromazine ion (1+)HMDB
CL-PPAHMDB
Didemethylchlorpromazine maleateHMDB
DidesmethylchlorpromazineHMDB
Chemical FormulaC15H15ClN2S
Average Molecular Weight290.811
Monoisotopic Molecular Weight290.064446887
IUPAC Name3-(2-chloro-10H-phenothiazin-10-yl)propan-1-amine
Traditional Name3-(2-chlorophenothiazin-10-yl)propan-1-amine
CAS Registry NumberNot Available
SMILES
NCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2
InChI Identifier
InChI=1S/C15H15ClN2S/c16-11-6-7-15-13(10-11)18(9-3-8-17)12-4-1-2-5-14(12)19-15/h1-2,4-7,10H,3,8-9,17H2
InChI KeyZTQZBABFEUDZFE-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
  • Tertiary aliphatic/aromatic amine
  • Aryl thioether
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Para-thiazine
  • Tertiary amine
  • Thioether
  • Azacycle
  • Primary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0098 g/LALOGPS
logP4.11ALOGPS
logP3.72ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.69 m³·mol⁻¹ChemAxon
Polarizability30.75 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+162.66230932474
DeepCCS[M-H]-160.30430932474
DeepCCS[M-2H]-193.1930932474
DeepCCS[M+Na]+168.75630932474
AllCCS[M+H]+162.132859911
AllCCS[M+H-H2O]+158.832859911
AllCCS[M+NH4]+165.132859911
AllCCS[M+Na]+166.032859911
AllCCS[M-H]-161.932859911
AllCCS[M+Na-2H]-161.232859911
AllCCS[M+HCOO]-160.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DedimethylchlorpromazineNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C23649.1Standard polar33892256
DedimethylchlorpromazineNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C22570.9Standard non polar33892256
DedimethylchlorpromazineNCCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C22560.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dedimethylchlorpromazine,1TMS,isomer #1C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C212643.4Semi standard non polar33892256
Dedimethylchlorpromazine,1TMS,isomer #1C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C212725.9Standard non polar33892256
Dedimethylchlorpromazine,1TMS,isomer #1C[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C213461.5Standard polar33892256
Dedimethylchlorpromazine,2TMS,isomer #1C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C2789.7Semi standard non polar33892256
Dedimethylchlorpromazine,2TMS,isomer #1C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C2987.4Standard non polar33892256
Dedimethylchlorpromazine,2TMS,isomer #1C[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C3344.5Standard polar33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C212849.8Semi standard non polar33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C212958.6Standard non polar33892256
Dedimethylchlorpromazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C213512.0Standard polar33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3224.6Semi standard non polar33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3362.6Standard non polar33892256
Dedimethylchlorpromazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCN1C2=CC=CC=C2SC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C3384.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dedimethylchlorpromazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-8390000000-8f38a5b037f5a46a73262017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dedimethylchlorpromazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dedimethylchlorpromazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Positive-QTOFsplash10-006x-0090000000-ca69f8fab5a979750e242017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Positive-QTOFsplash10-00dl-4090000000-899005d20b5dde2bd5132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Positive-QTOFsplash10-0006-9130000000-e9c04b2f6d25011bc6b42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Negative-QTOFsplash10-000i-0090000000-6ebd93710121b1f465af2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Negative-QTOFsplash10-003j-0790000000-17240704136fa50cf2892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Negative-QTOFsplash10-001i-2290000000-1ba927b7257079f28b262017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Positive-QTOFsplash10-0006-0090000000-6fd6a843191ad3b271a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Positive-QTOFsplash10-00di-0090000000-b3d3f424c3397fc18ac12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Positive-QTOFsplash10-0012-0090000000-c5d4b66055e942d7a4822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 10V, Negative-QTOFsplash10-000i-0090000000-61f66f99a164a1f9cb8d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 20V, Negative-QTOFsplash10-000i-0090000000-5d1d09be58dea441da702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dedimethylchlorpromazine 40V, Negative-QTOFsplash10-001i-7290000000-6eb544dfe643974d616c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound74981
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available