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CAS 469887-29-4

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Norbuprenorphine glucuronide

Description:
Norbuprenorphine glucuronide is a metabolite of buprenorphine, an opioid used primarily for pain management and in the treatment of opioid addiction. This compound is characterized by its glucuronidation, a biochemical process where a glucuronic acid molecule is conjugated to norbuprenorphine, enhancing its solubility and facilitating excretion. As a polar compound, norbuprenorphine glucuronide is typically found in urine and is often measured in drug testing to monitor buprenorphine use. Its pharmacological activity is significantly lower than that of its parent compound, buprenorphine, which acts as a partial agonist at opioid receptors. The presence of norbuprenorphine glucuronide in biological samples can indicate recent buprenorphine administration, making it a useful biomarker in clinical and forensic toxicology. Additionally, understanding its characteristics is essential for interpreting drug metabolism and pharmacokinetics in patients undergoing treatment with buprenorphine.
Formula:C31H43NO10
InChI:InChI=1S/C31H43NO10/c1-27(2,3)28(4,38)16-13-29-8-9-31(16,39-5)26-30(29)10-11-32-17(29)12-14-6-7-15(22(42-26)18(14)30)40-25-21(35)19(33)20(34)23(41-25)24(36)37/h6-7,16-17,19-21,23,25-26,32-35,38H,8-13H2,1-5H3,(H,36,37)/t16-,17-,19+,20+,21-,23+,25-,26-,28+,29-,30+,31-/m1/s1
InChI key:InChIKey=OOLGGESLZHGXGC-TXYLTYGDSA-N
SMILES:O(C)[C@@]12[C@]3([C@@]45[C@@]([C@@](CC6=C4C(O3)=C(O[C@@H]7O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]7O)C=C6)(NCC5)[H])(C[C@@]1([C@](C(C)(C)C)(C)O)[H])CC2)[H]
Synonyms:
  • Norbuprenorphine 3-β-D-glucuronide
  • Norbuprenorphine glucuronide
  • (5α,7α)-4,5-Epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl β-D-glucopyranosiduronic acid
  • β-D-Glucopyranosiduronic acid, (5α,7α)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl
  • Norbuprenorphine 3-glucuronide
  • Norbuprenorphine 3--D-Glucuronide
  • OOLGGESLZHGXGC-UKLQGZGASA-N
  • Norbuprenorphine 3--D-Glucuronide (1.0mg/ml in Acetonitrile)
  • (5a,7a)-4,5-Epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl -D-Glucopyranosiduronic Acid
  • Norbuprenorphine 3-β-D-Glucuronide (~90%)
  • Norbuprenorphine glucuronide solution
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