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Morphine-3-glucuronide

Topic: Chemistry

 From HandWiki - Reading time: 7 min

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
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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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 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.[4][page needed] Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.

See also

References

  1. ↑ "Human UGT2B7 catalyzes morphine glucuronidation". Drug Metab. Dispos. 25 (1): 1–4. 1 January 1997. PMID 9010622. http://dmd.aspetjournals.org/cgi/content/abstract/25/1/1. 
  2. ↑ "Interactions between morphine and the morphine-glucuronides measured by conditioned place preference and locomotor activity". Pharmacology Biochemistry and Behavior 93 (1): 1–9. July 2009. doi:10.1016/j.pbb.2009.03.013. PMID 19351545. 
  3. ↑ "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. July 2009. 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.). 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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