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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:50:15 UTC
Update Date2021-09-14 15:47:06 UTC
HMDB IDHMDB0041962
Secondary Accession Numbers
  • HMDB41962
Metabolite Identification
Common NameNorpropoxyphene
DescriptionNorpropoxyphene is a major metabolite of the opioid analgesic drug dextropropoxyphene, and is responsible for many of the side effects associated with use of this drug, especially the unusual toxicity seen during dextropropoxyphene overdose. It has weaker analgesic effects than dextropropoxyphene itself, but is a relatively potent pro-convulsant and blocker of sodium and potassium channels, particularly in heart tissue, which produces prolonged intracardiac conduction time and can lead to heart failure following even relatively minor overdoses. The toxicity of this metabolite makes dextropropoxyphene up to 10 times more likely to cause death following overdose compared to other similar mild opioid analgesics, and has led to dextropropoxyphene being withdrawn from the market in some countries.
Structure
Thumb
Synonyms
ValueSource
1,2-Diphenyl-4-(methylamino)-3-methyl-2-butanol propionateHMDB
Norpropoxyphene #1HMDB
Norpropoxyphene #2HMDB
Norpropoxyphene maleate, (S-(r*,s*))-isomerHMDB
Norpropoxyphene citrate, (S-(r*,s*))-isomerHMDB
Norpropoxyphene maleate (1:1)HMDB
Norpropoxyphene, (S-(r*,s*))-isomerHMDB
NordextropropoxypheneHMDB
3-Methyl-4-(methylamino)-1,2-diphenylbutan-2-yl propanoic acidHMDB
NorpropoxypheneMeSH
Chemical FormulaC21H27NO2
Average Molecular Weight325.4446
Monoisotopic Molecular Weight325.204179113
IUPAC Name3-methyl-4-(methylamino)-1,2-diphenylbutan-2-yl propanoate
Traditional Namenorpropoxyphene
CAS Registry Number66796-40-5
SMILES
CCC(=O)OC(CC1=CC=CC=C1)(C(C)CNC)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H27NO2/c1-4-20(23)24-21(17(2)16-22-3,19-13-9-6-10-14-19)15-18-11-7-5-8-12-18/h5-14,17,22H,4,15-16H2,1-3H3
InChI KeyIKACRWYHQXOSGM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylbutylamine
  • Benzyloxycarbonyl
  • Phenylpropane
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Secondary amine
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111686
KNApSAcK IDNot Available
Chemspider ID17756
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorpropoxyphene
METLIN IDNot Available
PubChem Compound18804
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