Morphine-3-glucuronide

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Morphine-3-glucuronide
Morphine-3-glucuronide.svg
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.150.265
MeSH Morphine-3-glucuronide
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

Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7.[1] It is not active as an opioid agonist,[2] but does have some action as a convulsant, which does not appear to be mediated through opioid receptors,[3] 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.[4][page needed] Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.

See also[edit]

References[edit]

  1. ^ Coffman BL, Rios GR, King CD, Tephly TR (1 January 1997). "Human UGT2B7 catalyzes morphine glucuronidation". Drug Metab. Dispos. 25 (1): 1–4. PMID 9010622.
  2. ^ 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.
  3. ^ 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.
  4. ^ Bertram G. Katzung; Susan B. Masters; Anthony J. Trevor. Basic & Clinical Pharmacology (11th ed.).