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Merck
CN

M6886

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
UNSPSC Code:
12352200
PubChem Substance ID:
24897126
MDL number:
MFCD00056773

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, kontrollierte Droge in Deutschland

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.

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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
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
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
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