morphine-3-glucuronide

{{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={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4588593

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WAEXKFONHRHFBZ-ZXDZBKESSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 20290-09-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = O27Z9CH39A

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1329

| PubChem = 5484731

| 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

| MeSHName = Morphine-3-glucuronide

}}

|Section2={{Chembox Properties

| Formula=C₂₃H₂₇NO₉

| MolarMass=461.462 g/mol

| Appearance=

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|Section3={{Chembox Hazards

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Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7.{{cite journal | vauthors = Coffman BL, Rios GR, King CD, Tephly TR | title = Human UGT2B7 catalyzes morphine glucuronidation | journal = Drug Metab. Dispos. | volume = 25 | issue = 1 | pages = 1–4 | date = 1 January 1997 | pmid = 9010622 | url = http://dmd.aspetjournals.org/cgi/content/abstract/25/1/1 }} It is not active as an opioid agonist,{{cite journal |vauthors=Vindenes V, Ripel A, Handal M, Boix F, Mørland J |title=Interactions between morphine and the morphine-glucuronides measured by conditioned place preference and locomotor activity |journal=Pharmacology Biochemistry and Behavior |volume=93 |issue=1 |pages=1–9 |date=July 2009 |pmid=19351545 |doi=10.1016/j.pbb.2009.03.013 |s2cid=5328449 }} but does have some action as a convulsant, which does not appear to be mediated through opioid receptors,{{cite journal |vauthors=Hemstapat K, Le L, Edwards SR, Smith MT |title=Comparative studies of the neuro-excitatory behavioural effects of morphine-3-glucuronide and dynorphin a(2-17) following spinal and supraspinal routes of administration |journal=Pharmacology Biochemistry and Behavior |volume= 93|issue= 4|pages= 498–505|date=July 2009 |pmid=19580825 |doi=10.1016/j.pbb.2009.06.016 |s2cid=207331030 }} 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.{{cite book|author1=Bertram G. Katzung |author2=Susan B. Masters |author3=Anthony J. Trevor | title = Basic & Clinical Pharmacology | edition = 11th}}{{page needed|date=June 2019}} Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.