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Merck
CN

M6886

Sigma-Aldrich

Morphine 3-β-D-glucuronide

Synonym(s):

M3G

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About This Item

Empirical Formula (Hill Notation):
C23H27NO9
CAS Number:
20290-09-9
Molecular Weight:
461.46
MDL number:
MFCD00056773
UNSPSC Code:
12352200
PubChem Substance ID:
24897126

Key Documents

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drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

SMILES string

[H][C@]12Oc3c(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)ccc5C[C@@H]6C(C=C[C@@H]1O)[C@@]2(CCN6C)c35

Biochem/physiol Actions

Metabolite of morphine that is devoid of antinociceptic activity; hyperglycemic and neuroexcitatory effects appear to be mediated via a non-opioid mechanism.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H336

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
039K1343
011H3895
051F3831

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M T Smith
Clinical and experimental pharmacology & physiology, 27(7), 524-528 (2000-06-30)
1. Morphine is recommended by the World Health Organization as the drug of choice for the management of moderate to severe cancer pain. 2. Education of health professionals in the past decade has resulted in a large increase in the
Y Hashiguchi et al.
Brain research, 694(1-2), 13-20 (1995-10-02)
The greater potency of morphine-6-glucuronide (M6G) as well as the inactivity of morphine-3-glucuronide (M3G) with respect to the antinociceptive effects of the parent molecule, morphine (MOR), have been well established. It has been suggested that M3G is an antagonist of
S V Löser et al.
Naunyn-Schmiedeberg's archives of pharmacology, 354(2), 192-197 (1996-07-01)
We investigated the nature of interaction of morphine-3-O-beta-D-glucuronide (M3G) and morphine-6-O-beta-D-glucuronide (M6G) with opioid binding sites at the mu-, delta- and kappa-opioid receptors (mu-OR, delta-OR and kappa-OR) in cerebral membranes. Saturation binding experiments revealed a competitive interaction of M6G with
Maarten Swartjes et al.
Molecular medicine (Cambridge, Mass.), 18, 1320-1326 (2012-09-25)
Opioid-induced hyperalgesia (OIH) is a paradoxical increase in pain perception that may manifest during opioid treatment. For morphine, the metabolite morphine-3-glucuronide (M3G) is commonly believed to underlie this phenomenon. Here, in three separate studies, we empirically assess the role of
Michael R Due et al.
Journal of neuroinflammation, 9, 200-200 (2012-08-18)
Multiple adverse events are associated with the use of morphine for the treatment of chronic non-cancer pain, including opioid-induced hyperalgesia (OIH). Mechanisms of OIH are independent of opioid tolerance and may involve the morphine metabolite morphine-3-glucuronide (M3G). M3G exhibits limited
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