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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:50:03 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0041959
Secondary Accession Numbers
  • HMDB41959
Metabolite Identification
Common NameNormorphine
DescriptionNormorphine, also known as desmethylmorphine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. Normorphine is a very strong basic compound (based on its pKa). Its formation from morphine is catalyzed by the liver enzymes CYP3A4 and CYP2C8. Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States, it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity.
Structure
Data?1583425260
Synonyms
ValueSource
DesmethylmorphineHMDB
Normorphine perchlorateHMDB
N-DemethylmorphineHMDB
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol hydrochlorideHMDB
4,5-Epoxy-3,6-dihydroxymorphin-7-eneHMDB
Normorphine hydrochlorideHMDB
Normorphine sulfamateHMDB
(-)-NormorphineHMDB
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diolHMDB
(5Α,6α)-7,8-didehydro-4,5-epoxymorphinan-3,6-diolHMDB
4,5-Epoxy-3,6-dihydromorphin-7-eneHMDB
DemethylmorphineHMDB
N-NormorphineHMDB
NormorphineHMDB
Chemical FormulaC16H17NO3
Average Molecular Weight271.316
Monoisotopic Molecular Weight271.120843411
IUPAC Name(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol
Traditional Name(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol
CAS Registry Number466-97-7
SMILES
[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O
InChI Identifier
InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1
InChI KeyONBWJWYUHXVEJS-ZTYRTETDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Secondary aliphatic amine
  • Ether
  • Oxacycle
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point273 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.17Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.19 g/LALOGPS
logP10(0.4) g/LALOGPS
logP10(0.26) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.83 m³·mol⁻¹ChemAxon
Polarizability27.75 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Normorphine[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O3787.2Standard polar33892256
Normorphine[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O2423.1Standard non polar33892256
Normorphine[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O2488.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Normorphine,1TMS,isomer #1C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O52467.3Semi standard non polar33892256
Normorphine,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]352503.2Semi standard non polar33892256
Normorphine,1TMS,isomer #3C[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C52500.7Semi standard non polar33892256
Normorphine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)C=C[C@@H]352507.3Semi standard non polar33892256
Normorphine,2TMS,isomer #2C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C)[C@H]1O52500.5Semi standard non polar33892256
Normorphine,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2507.8Semi standard non polar33892256
Normorphine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2537.1Semi standard non polar33892256
Normorphine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C2646.5Standard non polar33892256
Normorphine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O52746.0Semi standard non polar33892256
Normorphine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]352775.7Semi standard non polar33892256
Normorphine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C52722.9Semi standard non polar33892256
Normorphine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@@H]352990.2Semi standard non polar33892256
Normorphine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C(C)(C)C)[C@H]1O52957.8Semi standard non polar33892256
Normorphine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C2960.0Semi standard non polar33892256
Normorphine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C3235.5Semi standard non polar33892256
Normorphine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C3323.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Normorphine 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 - Normorphine 10V, Positive-QTOFsplash10-00di-0090000000-0ce88f6c7aacd22857e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normorphine 20V, Positive-QTOFsplash10-00di-0090000000-c13b47c233a54b20d3a82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normorphine 40V, Positive-QTOFsplash10-00di-0090000000-e760b6a34c0df4dae8c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normorphine 10V, Negative-QTOFsplash10-00di-0090000000-19dbfadd3d4c178682782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normorphine 20V, Negative-QTOFsplash10-00di-0090000000-19dbfadd3d4c178682782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Normorphine 40V, Negative-QTOFsplash10-01b9-0090000000-d773172bb6e200eaed9a2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 ID4575435
KEGG Compound IDC11785
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNormorphine
METLIN IDNot Available
PubChem Compound5462508
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