Morphine-3-glucuronide

Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7. It is not active as an opioid agonist, but does have some action as a convulsant, which does not appear to be mediated through opioid receptors, but rather through interaction with glycine and/or GABA receptors. As a polar compound, it has a limited ability to cross the blood–brain barrier, but kidney failure may lead to its accumulation and result in seizures. Probenecid and inhibitors of P-glycoprotein can enhance uptake of morphine-3-glucuronide and, to a lesser extent, morphine-6-glucuronide. Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.

Morphine-3-glucuronide
Names
IUPAC name
6α-Hydroxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-3-yl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-9-yl]oxy}oxane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Morphine-3-glucuronide
UNII
  • InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1 Y
    Key: WAEXKFONHRHFBZ-ZXDZBKESSA-N Y
  • O=C(O)[C@H]6O[C@@H](Oc2c1O[C@H]5[C@@H](O)\C=C/[C@H]4[C@@H]3N(C)CC[C@@]45c1c(cc2)C3)[C@H](O)[C@@H](O)[C@@H]6O
Properties
C23H27NO9
Molar mass 461.462 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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