Morphine-3-glucuronide
Identifiers | |
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20290-09-9 | |
ChEMBL | ChEMBL1329 |
ChemSpider | 4588593 |
Jmol 3D model | Interactive image |
MeSH | Morphine-3-glucuronide |
PubChem | 5484731 |
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Properties | |
C23H27NO9 | |
Molar mass | 461.462 g/mol |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox references | |
Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7.[citation needed] It is not active as an opioid agonist,[1] but does have some action as a convulsant, which does not appear to be mediated through opioid receptors,[2] 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 renal 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.[3] Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.
See also
- Morphine-6-glucuronide
- 3-Monoacetylmorphine, the inactive 3,- position blocked by esterization (and thus inactive) of a semi-synthetic prodrug to morphine marking the same activity profile as the drug of this article
- Morphine-N-oxide
- Buprenorphine-3-glucuronide
References
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- Glucuronides
- Opioid metabolites
- Morphinans
- Alcohols
- Glycine receptor antagonists
- GABAA receptor negative allosteric modulators
- Convulsants
- Nervous system drug stubs