Morphine-3-glucuronide

Base Information

• Chemical Name: Morphine-3-glucuronide
• CAS No.: 20290-09-9
• Molecular Formula: C₂₃H₂₇NO₉
• Molecular Weight: 461.469
• European Community (EC) Number: 621-410-1
• UNII: O27Z9CH39A
• DSSTox Substance ID: DTXSID80174157
• Nikkaji Number: J125.691B
• Wikipedia: Morphine-3-glucuronide
• Wikidata: Q65707098
• Metabolomics Workbench ID: 49641
• ChEMBL ID: CHEMBL1329
• Mol file: 20290-09-9.mol

Synonyms:morphine-3-glucuronide;morphine-3beta-D-glucuronide

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Chemical Property of Morphine-3-glucuronide

Chemical Property:

• Vapor Pressure: 2.58E-23mmHg at 25°C
• Melting Point: 220-224°C
• Boiling Point: 745.1 ºCat 760 mmHg
• PKA: pKa 2.88 ± 0.01;8.21± 0.11(H2O,t =25,I=0.154(KCl))(Approximate)
• Flash Point: 404.4 ºC
• PSA: 149.15000
• Density: 1.64 g/cm³
• LogP: -1.29860
• Storage Temp.: 2-8°C
• XLogP3: -3
• 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:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 23/25-36/38-36-20/21-61-43-22-39/23/24/25-23/24/25-10-11
• Safety Statements: 36-45-53-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC6C(C(C(C(O6)C(=O)O)O)O)O)OC3C(C=C4)O
• Isomeric SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)O[C@H]3[C@H](C=C4)O
• Uses: Controlled Substance. Analog of Morphine; as molecular chameleon with unexpected lipophilicity. A metabolite of Morphine. Analog of Morphine as molecular chameleon with unexpected lipophilicity. Controlled substance.

Technology Process of Morphine-3-glucuronide

There total 37 articles about Morphine-3-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: 29.0%

morphine (57-27-2,143-70-4,6912-73-8,16206-77-2,27067-73-8,65165-99-3,70982-47-7) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → morphine 3-glucuronide (20290-09-9,116003-91-9)

Guidance literature:

With lithium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jm00108a005

Reference yield:

C32H37NO13 → Morphine 3-b-D-glucuronide (20290-09-9,116003-91-9)

Guidance literature:

With water; potassium hydroxide; In methanol; at -50 - -40 ℃; for 2h;

Reference yield:

C44H53NO13 → Morphine 3-b-D-glucuronide (20290-09-9,116003-91-9)

Guidance literature:

With water; sodium hydroxide; In ethanol; at -40 - -30 ℃; for 2h;

upstream raw materials:

MORPHIN

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

UDP-glucuronic acid

uridine-diphosphate-glucuronic acid triammonium salt

Refernces

• 1、 Boldt, Petra,Rothschild, Markus A.,Kaeferstein, Herbert. "Glucuronidation of paracetamol by human liver microsomes in vitro: Enzyme kinetic parameters and interactions with short-chain aliphatic alcohols and opiates". . p. 787 - 794. Retrieved 2008/09/19.
• 2、 Salvatella, Mariona,Arsequell, Gemma,Valencia, Gregorio,Rodriguez, Raquel E.. "A highly toxic morphine-3-glucuronide derivative". . p. 905 - 908. Retrieved 2007/10/03.