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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:12 UTC
Update Date2021-09-14 15:45:15 UTC
HMDB IDHMDB0061007
Secondary Accession Numbers
  • HMDB61007
Metabolite Identification
Common NameN-Desmethyltramadol
DescriptionN-Desmethyltramadol, also known as M2, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. N-Desmethyltramadol is a very strong basic compound (based on its pKa). N-Desmethyltramadol is a metabolite of tramadol. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. Within humans, N-desmethyltramadol participates in a number of enzymatic reactions. In particular, N-desmethyltramadol and formaldehyde can be biosynthesized from tramadol through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In addition, N-desmethyltramadol can be converted into N,N-didesmethyltramadol and formaldehyde through its interaction with the enzymes cytochrome P450 2B6 and cytochrome P450 3A4. In humans, N-desmethyltramadol is involved in tramadol metabolism pathway. 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. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia ).
Structure
Thumb
Synonyms
ValueSource
N-DemethyltramadolHMDB
N-MonodesmethyltramadolHMDB
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
Physiological effectNot Available
Disposition
Process
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
Predicted Chromatographic Properties
Spectra
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 ID23935864
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmetramadol
METLIN IDNot Available
PubChem Compound12149038
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