Morphine-6-glucuronide

Base Information

• Chemical Name: Morphine-6-glucuronide
• CAS No.: 20290-10-2
• Deprecated CAS: 155755-06-9,32205-91-7,28932-95-8
• Molecular Formula: C23H27 N O9
• Molecular Weight: 461.469
• European Community (EC) Number: 633-836-5
• UNII: 64Y9KYM60R
• DSSTox Substance ID: DTXSID40174158
• Nikkaji Number: J277.761D
• Wikipedia: Morphine-6-glucuronide
• Wikidata: Q4303469
• NCI Thesaurus Code: C166899
• Pharos Ligand ID: 4V4FBVKMFZ3C
• Metabolomics Workbench ID: 49642
• ChEMBL ID: CHEMBL1330
• Mol file: 20290-10-2.mol

Synonyms:morphine-6-glucuronide;morphine-6beta-glucuronide

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Chemical Property of Morphine-6-glucuronide

Chemical Property:

• Vapor Pressure: 1.8E-22mmHg at 25°C
• Melting Point: 237-240°C (dec.)
• Refractive Index: 1.731
• Boiling Point: 731.6°Cat760mmHg
• PKA: 2.79±0.70(Predicted)
• Flash Point: 396.3°C
• PSA: 149.15000
• Density: 1.64g/cm³
• LogP: -0.94750
• Storage Temp.: −20°C
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 461.16858144
• Heavy Atom Count: 33
• Complexity: 839

Purity/Quality:

Safty Information:

• Hazard Codes: Xn,T
• Statements: 20/21/22-43-39/23/24/25-10-23/24/25
• Safety Statements: 36-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)OC6C(C(C(C(O6)C(=O)O)O)O)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](C=C4)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
• Recent ClinicalTrials: An Efficacy and Safety Study to Compare Morphine 6-glucuronide (M6G) and Morphine in Patients Suffering With Post-Operative Pain for at Least 24 Hours
• Recent EU Clinical Trials: A RANDOMISED, DOUBLE BLIND STUDY TO COMPARE THE ANALGESIC EFFICACY AND SAFETY PROFILES OF MORPHINE-6-GLUCURONIDE AND MORPHINE SULPHATE, GIVEN AS A LOADING DOSE FOLLOWED BY PATIENT-CONTROLLED ANALGESIA (PCA), IN PATIENTS SUFFERING MODERATE TO SEVERE POST-OPERATIVE PAIN REQUIRING PCA FOR AT LEAST 24 HOURS
• Uses: Morphine 6-β-D-Glucuronide, is a major metabolite of Morphine that is a potent opioid receptor agonist. Analgesic (narcotic). Controlled Substance. Controlled Substance. Major metabolite of Morphine that is a potent opioid receptor agonist. Analgesic (narcotic)

Technology Process of Morphine-6-glucuronide

There total 2 articles about Morphine-6-glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

di(morphin-3-yl) terephthalate (1333038-82-6) + methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (92420-89-8) → morphine-6-glucuronide (20290-10-2) + MORPHIN (57-27-2)

Guidance literature:

di(morphin-3-yl) terephthalate; methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate; With trimethylsilyl trifluoromethanesulfonate; In chlorobenzene; at 25 ℃; for 0.5h;

With sodium hydroxide; In water;

DOI:10.1016/j.tetlet.2011.07.011

Reference yield:

uridine-diphosphate-glucuronic acid triammonium salt (78132-48-6) + MORPHIN (57-27-2) → Morphine 3-b-D-glucuronide (20290-09-9,116003-91-9) + morphine-6-glucuronide (20290-10-2)

Guidance literature:

With human liver microsomes; In phosphate buffer; for 0.75h; Enzyme kinetics;

DOI:10.1080/00498250600911028

Reference yield:

C65H111N27O14S2 + morphine-6-glucuronide (20290-10-2) → Syn1001

Guidance literature:

With benzotriazol-1-yl-oxopyrrolidinephosphonium*PF₆; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In N,N-dimethyl-formamide; for 0.333333h; sonication;

DOI:10.1124/jpet.104.081000

upstream raw materials:

uridine-diphosphate-glucuronic acid triammonium salt

MORPHIN

di(morphin-3-yl) terephthalate

methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

Refernces

• 1、 Wong,Grace Jr.,Wright,Browning,Grossman,Bai,Christ. "Glucuronidation in the chimpanzee (Pan troglodytes): Studies with acetaminophen, oestradiol and morphine". . p. 1178 - 1190. Retrieved 2008/12/22.