Morphine-3-glucuronide

Morphine-3-glucuronide
Identifiers
CAS number 20290-09-9 N
PubChem 5484731
ChemSpider 4588593 Y
MeSH Morphine-3-glucuronide
ChEMBL CHEMBL1329 Y
Jmol-3D images Image 1
Properties
Molecular formula C23H27NO9
Molar mass 461.462 g/mol
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7. 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]; it is mediated by GABA/glycinergic system. 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]

See also

References

  1. ^ Vindenes V, Ripel A, Handal M, Boix F, Mørland J (July 2009). "Interactions between morphine and the morphine-glucuronides measured by conditioned place preference and locomotor activity". Pharmacology, Biochemistry, and Behavior 93 (1): 1–9. doi:10.1016/j.pbb.2009.03.013. PMID 19351545. 
  2. ^ Hemstapat K, Le L, Edwards SR, Smith MT (July 2009). "Comparative studies of the neuro-excitatory behavioural effects of morphine-3-glucuronide and dynorphin a(2-17) following spinal and supraspinal routes of administration". Pharmacology, Biochemistry, and Behavior 93 (4): 498–505. doi:10.1016/j.pbb.2009.06.016. PMID 19580825. 
  3. ^