Record Information
Version1.0
Creation date2015-05-07 20:47:30 UTC
Update date2019-11-26 03:22:03 UTC
Primary IDFDB031008
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namemorphine
DescriptionMorphine, also known as (-)-morphine or morphine sulfate, is a member of the class of compounds known as morphinans. Morphinans 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. Morphine is soluble (in water) and a very weakly acidic compound (based on its pKa). Morphine can be synthesized from morphinan. Morphine is also a parent compound for other transformation products, including but not limited to, myrophine, heroin, and codeine. Morphine can be found in a number of food items such as nanking cherry, eggplant, millet, and common hazelnut, which makes morphine a potential biomarker for the consumption of these food products. Morphine can be found primarily in blood and urine, as well as in human kidney and liver tissues. In humans, morphine is involved in several metabolic pathways, some of which include heroin action pathway, morphine metabolism pathway, heroin metabolism pathway, and codeine metabolism pathway. Morphine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Morphine is a drug which is used for the relief and treatment of severe pain. The primary source of morphine is isolation from poppy straw of the opium poppy. In 2013, an estimated 523 000 kg of morphine were produced. About 45 000 kg were used directly for pain, a four-time increase over the last twenty years. Most use for this purpose was in the developed world. About 70% of morphine is used to make other opioids such as hydromorphone, oxymorphone, and heroin. It is a Schedule II drug in the United States, Class A in the United Kingdom, and Schedule I in Canada. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Morphine is sold under many trade names . Primarily hepatic (90%), converted to dihydromorphinone and normorphineand is) also converted to morphine-3-glucuronide (M3G) and morphine-6-glucuronide. Virtually all morphine is converted to glucuronide metabolites; only a small fraction (less than 5%) of absorbed morphine is demethylated (DrugBank). In the treatment of morphine overdosage, primary attention should be given to the re- establishment of a patent airway and institution of assisted or controlled ventilation. Supportive measures (including oxygen, vasopressors) should be employed in the management of circulatory shock and pulmonary edema accompanying overdose as indicated. Cardiac arrest or arrhythmias may require cardiac massage or defibrillation. The pure opioid antagonists, such as naloxone, are specific antidotes against respiratory depression which results from opioid overdose. Naloxone should be administered intravenously; however, because its duration of action is relatively short, the patient must be carefully monitored until spontaneous respiration is reliably re-established. If the response to naloxone is suboptimal or not sustained, additional naloxone may be administered, as needed, or given by continuous infusion to maintain alertness and respiratory function; however, there is no information available about the cumulative dose of naloxone that may be safely administered (L1712) (T3DB).
CAS Number57-27-2
Structure
Thumb
Synonyms
SynonymSource
(-)-MorphineChEBI
(5alpha,6alpha)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diolChEBI
(5alpha,6alpha)-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diolChEBI
(5R,6S,9R,13S,14R)-4,5-Epoxy-N-methyl-7-morphinen-3,6-diolChEBI
(7R,7AS,12BS)-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diolChEBI
MorfinaChEBI
MorphiaChEBI
MorphinChEBI
MorphinumChEBI
MorphiumChEBI
Morfina dosaKegg
SubstitolKegg
(5a,6a)-17-Methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diolGenerator
(5Α,6α)-17-methyl-7,8-didehydro-4,5-epoxymorphinan-3,6-diolGenerator
(5a,6a)-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diolGenerator
(5Α,6α)-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diolGenerator
D-(-)-MorphineHMDB
MorphinaHMDB
Morphine sulfateHMDB
Contin, MSHMDB
Morphine chlorideHMDB
Morphine sulfate (2:1), anhydrousHMDB
Oramorph SRHMDB
Sulfate, morphineHMDB
Chloride, morphineHMDB
MS ContinHMDB
DuramorphHMDB
Morphine sulfate (2:1), pentahydrateHMDB
Predicted Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
logP0.99ALOGPS
logP0.9ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.26ChemAxon
pKa (Strongest Basic)9.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.12 m³·mol⁻¹ChemAxon
Polarizability29.95 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H19NO3
IUPAC name(1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene-10,14-diol
InChI IdentifierInChI=1S/C17H19NO3/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/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
InChI KeyBQJCRHHNABKAKU-KBQPJGBKSA-N
Isomeric SMILES[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
Classification
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
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSmorphine, non-derivatized, GC-MS Spectrumsplash10-00li-8970000000-28acaf307ce4bc5aabf1Spectrum
GC-MSmorphine, non-derivatized, GC-MS Spectrumsplash10-014i-0090000000-b9cf42b077ae0fa5b50dSpectrum
GC-MSmorphine, non-derivatized, GC-MS Spectrumsplash10-00li-8970000000-28acaf307ce4bc5aabf1Spectrum
GC-MSmorphine, non-derivatized, GC-MS Spectrumsplash10-014i-0090000000-b9cf42b077ae0fa5b50dSpectrum
Predicted GC-MSmorphine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00vl-1090000000-adcd23ce75ad17f72cc5Spectrum
Predicted GC-MSmorphine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03mi-7209800000-b1a234139ee9e72f3402Spectrum
Predicted GC-MSmorphine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-98125212ed8e73f219e1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-e9f7be236d827a716c1bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0290000000-5066e10cd96a2c376676Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kui-0930000000-793deeb91de6d2459cbeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-100r-0900000000-f775c77035946f746daaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0390000000-660ff44516f98e346016Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-22857c8ef81e65ad6bd3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-c5194c99a9e7f30ea0c8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-1980ff8ab9e654f16fe1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0690000000-efa51d970eaf96d3b982Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pc9-0920000000-64a693f2f51c03129c94Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-100r-0900000000-49174c3db4b1c1847080Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-3cc8784093ef460d3030Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-4bc885836f18b77696f3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-4a16648c3e86669f2446Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0690000000-f41b2f804790e9ad8f1dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pc9-0920000000-69393fc6563baf39d91fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-100r-0900000000-467f39309be5edfa4c01Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0390000000-bd9670761ff2a7dafc55Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-46d12300d5a1a45af278Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-9470e4073083d671574aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdj-3290000000-3c229ae6f1433ae20d85Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-0d38f6180c7ffdd17c4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-e3fd836bcbf266246e22Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02di-0390000000-317675bcd07b96b05935Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference