Structure via PubChem · Public domain (PubChem)
Morphine-3-glucuronide
Sign in to saveMorphine-3-glucuronide is a metabolite of morphine produced by UGT2B7. It is not active as an opioid agonist, but does have some action as a convulsant, which does not appear to be mediated through opioid receptors, 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. Reported side effects relat
Chemical data
- Formula
- C23H27NO9
- Molecular weight
- 461.5 g/mol
- IUPAC name
- (2S,3S,4S,5R,6S)-6-[[(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
- SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)O[C@H]3[C@H](C=C4)O
- InChIKey
- WAEXKFONHRHFBZ-ZXDZBKESSA-N
- XLogP
- -3
- Polar surface area
- 149 Ų
- H-bond donors
- 5
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Research
709 papers- Morphine-3-Glucuronide, Physiology and Behavior.Frontiers in molecular neuroscience · 2022
- Morphine-3-glucuronide causes antinociceptive cross-tolerance to morphine and increases spinal substance P expression.European journal of pharmacology · 2020
- Is morphine-3-glucuronide of therapeutic relevance?Pain · 2005
- Pharmacokinetic analysis of morphine-3-glucuronide after acute morphine intravenous bolus administration to rats with traumatic brain injury.The Journal of pharmacology and experimental therapeutics · 2025
- Mechanism of allodynia evoked by intrathecal morphine-3-glucuronide in mice.International review of neurobiology · 2009
via PubMed
Wikidata facts
- Mass
- 461.168581444
Show 5 more facts
- isomeric SMILES
- [H][C@@]12CC3=C4C(O[C@H]5[C@@H](O)C=C[C@@H]1[C@@]45CCN2C)=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3
- chemical formula
- C₂₃H₂₇NO₉
- subject has role
- stimulant
- found in taxon
- Papaver somniferum
- canonical SMILES
- O=C(O)C1OC(OC2=CC=C3C4=C2OC5C(O)C=CC6C(N(C)CCC456)C3)C(O)C(O)C1O
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
{{chembox | Verifiedfields = changed | verifiedrevid = 462255487 | ImageFile = Morphine-3-glucuronide.svg | ImageClass = skin-invert-image | ImageSize = 250px | IUPACName = 6α-Hydroxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-3-yl β-D-glucopyranosiduronic acid | SystematicName = (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 | OtherNames = |Section1= |Section2= |Section3= }}
Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7. It is not active as an opioid agonist, but does have some action as a convulsant, which does not appear to be mediated through opioid receptors, 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. Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.
Excerpted from Wikipedia’s “Morphine-3-glucuronide” article, available under the CC BY-SA 4.0 licence.