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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:49:26 UTC
HMDB IDHMDB0014440
Secondary Accession Numbers
  • HMDB14440
Metabolite Identification
Common NameMorphine
DescriptionMorphine is only found in individuals that have used or taken this drug. It is the principal alkaloid in opium and the prototype opiate analgesic and narcotic. Morphine has widespread effects in the central nervous system and on smooth muscle. [PubChem]The precise mechanism of the analgesic action of morphine is unknown. However, specific CNS opiate receptors have been identified and likely play a role in the expression of analgesic effects. Morphine first acts on the mu-opioid receptors. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and to electrical stimulation.It has been shown that morphine binds to and inhibits GABA inhibitory interneurons. These interneurons normally inhibit the descending pain inhibition pathway. So, without the inhibitory signals, pain modulation can proceed downstream.
Structure
Thumb
Synonyms
ValueSource
(-)-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
(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, MSMeSH
Morphine chlorideMeSH
Morphine sulfate (2:1), anhydrousMeSH
Oramorph SRMeSH
Sulfate, morphineMeSH
Chloride, morphineMeSH
MS ContinMeSH
DuramorphMeSH
Morphine sulfate (2:1), pentahydrateMeSH
Chemical FormulaC17H19NO3
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
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
Traditional Namemorph
CAS Registry Number57-27-2
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point255 °C (sulfate salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility10.2 g/LNot Available
LogP0.8Not Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00li-8970000000-28acaf307ce4bc5aabf1View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-014i-0090000000-b9cf42b077ae0fa5b50dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00li-8970000000-28acaf307ce4bc5aabf1View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-014i-0090000000-b9cf42b077ae0fa5b50dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vl-1090000000-adcd23ce75ad17f72cc5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03mi-7209800000-b1a234139ee9e72f3402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-98125212ed8e73f219e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-e9f7be236d827a716c1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0290000000-5066e10cd96a2c376676View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kui-0930000000-793deeb91de6d2459cbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-100r-0900000000-f775c77035946f746daaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0390000000-660ff44516f98e346016View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-22857c8ef81e65ad6bd3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-c5194c99a9e7f30ea0c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-1980ff8ab9e654f16fe1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0690000000-efa51d970eaf96d3b982View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pc9-0920000000-64a693f2f51c03129c94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-100r-0900000000-49174c3db4b1c1847080View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-3cc8784093ef460d3030View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-4bc885836f18b77696f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0090000000-4a16648c3e86669f2446View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0690000000-f41b2f804790e9ad8f1dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pc9-0920000000-69393fc6563baf39d91fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-100r-0900000000-467f39309be5edfa4c01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ufr-0390000000-bd9670761ff2a7dafc55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-46d12300d5a1a45af278View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-9470e4073083d671574aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdj-3290000000-3c229ae6f1433ae20d85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-0d38f6180c7ffdd17c4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-e3fd836bcbf266246e22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02di-0390000000-317675bcd07b96b05935View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00295 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00295 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00295
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001889
Chemspider ID4450907
KEGG Compound IDC01516
BioCyc IDMORPHINE
BiGG IDNot Available
Wikipedia LinkMorphine
METLIN IDNot Available
PubChem Compound5288826
PDB IDMOI
ChEBI ID17303
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loguinov AV, Anderson LM, Crosby GJ, Yukhananov RY: Gene expression following acute morphine administration. Physiol Genomics. 2001 Aug 28;6(3):169-81. [PubMed:11526201 ]
  2. Kilpatrick GJ, Smith TW: Morphine-6-glucuronide: actions and mechanisms. Med Res Rev. 2005 Sep;25(5):521-44. [PubMed:15952175 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Coffman BL, Rios GR, King CD, Tephly TR: Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4. [PubMed:9010622 ]
  2. Takeda S, Ishii Y, Iwanaga M, Mackenzie PI, Nagata K, Yamazoe Y, Oguri K, Yamada H: Modulation of UDP-glucuronosyltransferase function by cytochrome P450: evidence for the alteration of UGT2B7-catalyzed glucuronidation of morphine by CYP3A4. Mol Pharmacol. 2005 Mar;67(3):665-72. Epub 2004 Dec 20. [PubMed:15611481 ]
  3. Yamada H, Ishii K, Ishii Y, Ieiri I, Nishio S, Morioka T, Oguri K: Formation of highly analgesic morphine-6-glucuronide following physiologic concentration of morphine in human brain. J Toxicol Sci. 2003 Dec;28(5):395-401. [PubMed:14746343 ]
  4. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Abildskov K, Weldy P, Garland M: Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53. doi: 10.1124/dmd.109.030635. Epub 2010 Jan 13. [PubMed:20071451 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [PubMed:18187562 ]
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
Morphine + Uridine diphosphate glucuronic acid → Morphine-3-glucuronide + Uridine 5'-diphosphatedetails
Morphine + Uridine diphosphate glucuronic acid → Morphine-6-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Ohno S, Kawana K, Nakajin S: Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94. doi: 10.1124/dmd.107.019281. Epub 2008 Jan 10. [PubMed:18187562 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
  2. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]

Only showing the first 10 proteins. There are 25 proteins in total.