Morphine-3-glucuronide

Morphine-3-glucuronide
Identifiers
CAS number	20290-09-9 Y
PubChem	5484731
ChemSpider	4588593 Y
MeSH	Morphine-3-glucuronide
Jmol-3D images	Image 1
SMILES 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
InChI 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 InChI=1/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 Key: WAEXKFONHRHFBZ-ZXDZBKESBI
Properties
Molecular formula	C23H27NO9
Molar mass	461.462 g/mol
Y (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

• Glucuronide
• 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 drug of this article
• Morphine-N-oxide

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. ^ Template:Bertram G. Katzung, Susan B. Masters, Anthony J. Trevor