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
ChEMBL
ChemSpider
MeSH
Morphine-3-glucuronide
UNII
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
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
Properties
C23 H27 NO9
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).
Chemical compound
Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7 .[1] opioid agonist ,[2] convulsant , which does not appear to be mediated through opioid receptors ,[3] 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 .
YouTube Encyclopedic
1 / 5
Views: 664
1 385
530
312
2 223
OPIOID ANALGESICS Part 3 Morphine Pharmacokinetics | MUST KNOW | EASY LEARNING | PHARMACOLOGY
13 Phase II reactions UDP glucuronosyltransferases example of morphine and NSAIDs
Morphine Chemistry and SAR
Outpatient Drug Testing and Detection 5/13/20
See also References
^ 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 . ^ 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 . S2CID 5328449 . ^ 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 . S2CID 207331030 . ^ Bertram G. Katzung; Susan B. Masters; Anthony J. Trevor. Basic & Clinical Pharmacology (11th ed.).
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P)tribromoethanol , trichloroethanol , trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital , sodium thiopental )Chlormethiazole D12-116
Dihydropyridines (e.g., nicardipine )Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584, tropisetron , zatosetron )
Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate
Dendrobine Diaboline
Endocannabinoids (e.g., 2-AG , anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ
Isobutyric acid Isonipecotic acid Isostrychnine
Laudanosine N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid Pitrazepin Pseudostrychnine
Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA)RU-5135
Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )Corymine
Cyanotriphenylborate
Daidzein Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )Furosemide Genistein Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A, ginkgolide B , ginkgolide C, ginkgolide J, ginkgolide M))Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )Picrotoxin (i.e., picrotin and picrotoxinin )PMBA
Riluzole Tropeines (e.g., bemesetron , LY-278584, tropisetron , zatosetron )
Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBLAlcohols (e.g., drinking alcohol , 2M2B )Anabolic steroids Avermectins (e.g., ivermectin )Barbiturates (e.g., phenobarbital )Benzodiazepines (e.g., diazepam )Bromide compounds (e.g., potassium bromide )Carbamates (e.g., meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g., mefenamic acid )Flavonoids (e.g., apigenin , hispidulin )Fluoxetine Flupirtine Imidazoles (e.g., etomidate )Kava constituents (e.g., kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))Norfluoxetine Petrichloral Phenols (e.g., propofol )Phenytoin Piperidinediones (e.g., glutethimide )Propanidid Pyrazolopyridines (e.g., etazolate )Quinazolinones (e.g., methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin )Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) )
Topiramate Valerian constituents (e.g., valerenic acid )Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )Negative modulators: 1,3M1B3M2B
11-Ketoprogesterone 17-Phenylandrostenol α5IA (LS-193,268) β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO )BIDN Bilobalide Bupropion CHEB
Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB
DMCM DMPC
EBOB Etbicyphat
FG-7142 (ZK-31906) Fiproles (e.g., fipronil )
Flavonoids (e.g., amentoflavone , oroxylin A )Flumazenil Fluoroquinolones (e.g., ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Leptazol Lindane MaxiPost
Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )Pregnenolone sulfate Propybicyphat
PWZ-029 Radequinil Ro 15-4513 Ro 19-4603
RO4882224
RO4938581
Sarmazenil SCS
Suritozole TB-21007 TBOB
TBPS TCS-1105
Terbequinil TETS Thujone U-93631
Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Negative modulators: Compound 14
This page was last edited on 5 May 2023, at 00:38
This page was last edited on 5 May 2023, at 00:38