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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:12 UTC
Update Date2018-05-20 20:32:43 UTC
HMDB IDHMDB0061007
Secondary Accession Numbers
  • HMDB61007
Metabolite Identification
Common NameN-Desmethyltramadol
DescriptionN-Desmethyltramadol is a metabolite of tramadol. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
N-DemethyltramadolCAS
N-MonodesmethyltramadolCAS
M2HMDB
Chemical FormulaC15H23NO2
Average Molecular Weight249.354
Monoisotopic Molecular Weight249.172878985
IUPAC Name(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol
Traditional Name(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol
CAS Registry Number75377-45-6
SMILES
CNC[C@H]1CCCC[C@]1(O)C1=CC(OC)=CC=C1
InChI Identifier
InChI=1S/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3/t13-,15+/m1/s1
InChI KeyVUMQHLSPUAFKKK-HIFRSBDPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Cyclohexanol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.25 g/LALOGPS
logP2.55ALOGPS
logP2.07ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)9.89ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.97 m³·mol⁻¹ChemAxon
Polarizability28.72 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
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 ID23935864
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkDesmetramadol
      METLIN IDNot Available
      PubChem Compound12149038
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available