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CAS 101224-22-0

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Buprenorphine glucuronide

Description:
Buprenorphine glucuronide is a metabolite of buprenorphine, an opioid used primarily for pain management and in the treatment of opioid addiction. This compound is formed through the process of glucuronidation, where a glucuronic acid molecule is conjugated to buprenorphine, enhancing its solubility and facilitating excretion. Buprenorphine glucuronide is characterized by its relatively high molecular weight and specific structural features that include a morphinan backbone. It is typically found in biological fluids, such as urine, and is often measured in pharmacokinetic studies to assess buprenorphine metabolism. The presence of this metabolite can indicate recent buprenorphine use and is important in clinical and forensic toxicology. While it is less pharmacologically active than its parent compound, understanding its characteristics is crucial for interpreting drug tests and managing opioid therapy effectively. Its detection can also provide insights into the metabolic pathways of buprenorphine and the potential for drug interactions.
Formula:C35H49NO10
InChI:InChI=1S/C35H49NO10/c1-31(2,3)32(4,42)20-15-33-10-11-35(20,43-5)30-34(33)12-13-36(16-17-6-7-17)21(33)14-18-8-9-19(26(46-30)22(18)34)44-29-25(39)23(37)24(38)27(45-29)28(40)41/h8-9,17,20-21,23-25,27,29-30,37-39,42H,6-7,10-16H2,1-5H3,(H,40,41)/t20-,21-,23+,24+,25-,27+,29-,30-,32+,33-,34+,35-/m1/s1
InChI key:InChIKey=CZULHKGIAJASAA-WWIHBJMFSA-N
SMILES:O(C)[C@@]12[C@]3([C@]45[C@@]([C@](N(CC6CC6)CC4)(CC7=C5C(O3)=C(O[C@@H]8O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]8O)C=C7)[H])(C[C@@]1([C@]([C@](C)(C)C)(C)O)[H])CC2)[H]
Synonyms:
  • (5,7)-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2,-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl -D-Glucuronide
  • (57-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2,-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl b-D-Glucuronide
  • (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-2-yl beta-D-glucopyranosiduronic acid
  • (5α,7α)-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid
  • Buprenorphine -D-Glucuronide
  • Buprenorphine 3-glucuronide
  • Buprenorphine 3-β-<span class="text-smallcaps">D</span>-glucuronide
  • Buprenorphine glucuronide
  • buprenorphine-3-O-glucuronide
  • β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, (5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl
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