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CAS 20736-11-2

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Codeine-6-glucuronide

Description:
Codeine-6-glucuronide is a metabolite of codeine, an opiate used primarily for its analgesic properties. It is formed in the liver through the process of glucuronidation, where a glucuronic acid molecule is conjugated to codeine, enhancing its solubility and facilitating excretion. This compound is characterized by its chemical formula, which reflects the addition of the glucuronic acid moiety to the codeine structure. Codeine-6-glucuronide is known for its pharmacological activity, contributing to the overall analgesic effects of codeine, although it is generally considered to be less potent than codeine itself. It is primarily excreted in urine and can be detected in various biological samples, making it relevant in drug testing and pharmacokinetic studies. The presence of this metabolite can provide insights into an individual's codeine use and metabolism. As with other opioids, the use of codeine and its metabolites must be carefully monitored due to the potential for dependence and adverse effects.
Formula:C24H29NO9
InChI:InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1
InChI key:InChIKey=CRWVOYRJXPDBPM-HSCJLHHPSA-N
SMILES:O([C@@H]1[C@]2([C@]34C=5C(O2)=C(OC)C=CC5C[C@]([C@@]3(C=C1)[H])(N(C)CC4)[H])[H])[C@@H]6O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]6O
Synonyms:
  • (5alpha,6alpha)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl beta-D-glucopyranosiduronic acid
  • Codeine glucuronide
  • Codeine-6-glucuronide
  • Codeine-6-β-<span class="text-smallcaps">D</span>-glucuronide
  • Glucopyranosiduronic acid, 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-yl, β-<span class="text-smallcaps">D</span>-
  • Glucopyranosiduronic acid, codeine, β-<span class="text-smallcaps">D</span>-
  • Morphinan, 7,8-didehydro-4,5α-epoxy-6α-(β-<span class="text-smallcaps">D</span>-glucopyranuronosyloxy)-3-methoxy-17-methyl-
  • Morphinan, β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid deriv.
  • beta-D-Galactopyranosiduronic acid, (5alpha,6alpha)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-yl
  • beta-D-Glucopyranosiduronic acid, (5alpha,6alpha)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-yl
  • See more synonyms
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