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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:24 UTC
Update Date2018-05-20 20:32:31 UTC
HMDB IDHMDB0060992
Secondary Accession Numbers
  • HMDB60992
Metabolite Identification
Common Name2-hydroxydesipramine
Description2-hydroxydesipramine is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2-Hydroxydesipramine monohydrochlorideMeSH
2-Hydroxydesipramine fumarateMeSH
2-Hydroxydesipramine monofumarateMeSH
2-OH-DMIMeSH
2-HydroxydesmethylimipramineMeSH
2-Hydroxy-desipramineMeSH
Chemical FormulaC18H22N2O
Average Molecular Weight282.3801
Monoisotopic Molecular Weight282.173213336
IUPAC Name2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
Traditional Name2-[3-(methylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
CAS Registry NumberNot Available
SMILES
CNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C18H22N2O/c1-19-11-4-12-20-17-6-3-2-5-14(17)7-8-15-13-16(21)9-10-18(15)20/h2-3,5-6,9-10,13,19,21H,4,7-8,11-12H2,1H3
InChI KeyNVJBOLMRGMDGLD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Alkyldiarylamine
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary amine
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility0.17 g/LALOGPS
logP3.34ALOGPS
logP3.17ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.63ChemAxon
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area35.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.29 m³·mol⁻¹ChemAxon
Polarizability33.13 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, Positivesplash10-00dl-5090000000-8e76a4f07afb1e4fce73View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9063000000-6e81780e6e12e98c3924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0090000000-bcb8aabdf8ebb58527c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul3-5090000000-40c13e82295f08b136dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9230000000-6fcc2799f8061fa4efb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3409ea36098e6ee2dfedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0090000000-08b72e43d94db0d0a433View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3690000000-7b5f4646b111996cb18bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound 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 Compound121249
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available