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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:29 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0060548
Secondary Accession Numbers
  • HMDB60548
Metabolite Identification
Common NameDihydromorphine
DescriptionDihydromorphine, also known as paramorphan or 6α-hydromorphol, 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. Dihydromorphine is a very strong basic compound (based on its pKa). In humans, dihydromorphine is involved in dihydromorphine action pathway. Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. As with nicomorphine, MDMA, heroin (DEA 2013 production quota: 25 grammes) and the like, dihydromorphine is also used in research such as that mentioned above in properly licensed facilities; Form 225, the most common and least expensive individual researcher's license, does not include Schedule I so the lab must have a higher-level DEA registration As with other licit opioids used for medical purposes in other countries, including even much weaker opioids like nicocodeine, benzylmorphine, and tilidine, the reason for dihydromorphine being in Schedule I is that it was not in medical use in the US at time the Controlled Substances Act of 1970 was drawn up. Dihydromorphine's onset of action is more rapid than morphine and it also tends to have a longer duration of action, generally 4–7 hours. In comparison, the relative potency of dihydrocodeine is 1.15 times that of codeine. Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine. Dihydromorphine, often labelled with the isotope tritium in the form of [3H]-dihydromorphine, is used in scientific research to study binding of the opioid receptors in the nervous system. Under the Controlled Substances Act, dihydromorphine is listed as a Schedule I substance along with heroin.
Structure
Data?1563866074
Synonyms
ValueSource
ParamorphanHMDB
ParamorfanHMDB
(5alpha,6alpha)-4,5-Epoxy-17-methylmorphinan-3,6-diolHMDB
(5Α,6α)-4,5-epoxy-17-methylmorphinan-3,6-diolHMDB
6alpha-7,8-DihydromorphineHMDB
6alpha-HydromorpholHMDB
6Α-7,8-dihydromorphineHMDB
6Α-hydromorpholHMDB
7,8-DihydromorphineHMDB
DHMHMDB
HydromorphineHMDB
alpha-DihydromorphineHMDB
Α-dihydromorphineHMDB
DihydromorphineHMDB
Chemical FormulaC17H21NO3
Average Molecular Weight287.3535
Monoisotopic Molecular Weight287.152143543
IUPAC Name(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
Traditional Name(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
CAS Registry Number509-60-4
SMILES
[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O
InChI Identifier
InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
InChI KeyIJVCSMSMFSCRME-KBQPJGBKSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM163.630932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.82 g/LALOGPS
logP1.26ALOGPS
logP1.08ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.16 m³·mol⁻¹ChemAxon
Polarizability30.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.79931661259
DarkChem[M-H]-162.2231661259
DeepCCS[M-2H]-209.04330932474
DeepCCS[M+Na]+185.09230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydromorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O3932.8Standard polar33892256
Dihydromorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O2334.6Standard non polar33892256
Dihydromorphine[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O2475.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydromorphine,1TMS,isomer #1CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C52414.1Semi standard non polar33892256
Dihydromorphine,1TMS,isomer #2CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C52472.6Semi standard non polar33892256
Dihydromorphine,2TMS,isomer #1CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C52480.4Semi standard non polar33892256
Dihydromorphine,1TBDMS,isomer #1CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C52677.9Semi standard non polar33892256
Dihydromorphine,1TBDMS,isomer #2CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C52744.8Semi standard non polar33892256
Dihydromorphine,2TBDMS,isomer #1CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C52926.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydromorphine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2090000000-64b6783f4c86622fea8f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydromorphine GC-MS (2 TMS) - 70eV, Positivesplash10-01di-6309700000-61de6f13f6659db9e2362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydromorphine 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 - Dihydromorphine 10V, Positive-QTOFsplash10-000i-0090000000-504a9b2ff60a0d7f44112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 20V, Positive-QTOFsplash10-000i-0090000000-c3e1bdcbec4cf28275c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 40V, Positive-QTOFsplash10-0kfx-4090000000-27a1656cb074b87c4b262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 10V, Negative-QTOFsplash10-000i-0090000000-6acbb360a4571844e9a12016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 20V, Negative-QTOFsplash10-000i-0090000000-6757484a2717da0640a02016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 40V, Negative-QTOFsplash10-00bc-0290000000-a1dc3f7fe7b08229191d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 10V, Positive-QTOFsplash10-000i-0090000000-8e23f9bfe8905382513a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 20V, Positive-QTOFsplash10-000i-0090000000-1ec5d5a94424722655522021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 40V, Positive-QTOFsplash10-000i-0090000000-ab4dccbaff63f6897f592021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 10V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 20V, Negative-QTOFsplash10-000i-0090000000-32affc6af32f5da1d2572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydromorphine 40V, Negative-QTOFsplash10-000i-0090000000-842b3a0fd7fd18ba1b062021-10-12Wishart 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 IDDB01565
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11782
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydromorphine
METLIN IDNot Available
PubChem Compound5359421
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