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M3528

Sigma-Aldrich

Morphine 6-β-D-glucuronide hydrate

≥90% (HPLC)

Synonym(s):

M6G

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About This Item

Empirical Formula (Hill Notation):
C23H27NO9 · 2H2O
CAS Number:
20290-10-2
Molecular Weight:
497.49
MDL number:
MFCD00167238
UNSPSC Code:
41116107
PubChem Substance ID:
24896850
NACRES:
NA.77

Assay

≥90% (HPLC)

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IA (Portugal)

storage temp.

−20°C

SMILES string

[H]O[H].[H]O[H].[H][C@]2(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C[C@@]3([H])[C@H]4Cc5ccc(O)c6O[C@]2([H])[C@]3(CCN4C)c56

InChI

1S/C23H27NO9.2H2O/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24;;/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30);2*1H2/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-;;/m0../s1

InChI key

NRBQUVXMCUQJPZ-WFLHAITMSA-N

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Biochem/physiol Actions

Major metabolite of morphine that is a potent μ−opioid receptor agonist.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332,H317

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Skin Sens. 1

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

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Certificates of Analysis (COA)

Lot/Batch Number
079H13831
079H1383
102K3350
041K3357
034H3363

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B Frances et al.
The Journal of pharmacology and experimental therapeutics, 262(1), 25-31 (1992-07-01)
The antinociceptive properties of morphine-6 beta-glucuronide (M6G) and morphine (oral, i.c.v. and s.c.) were examined in two tests involving different nociceptive stimuli [i.e., cutaneous-thermal (tail-flick) and chemical-visceral (acetic acid-writhing)] in both naive and chronically treated mice. Twenty min after i.c.v.
D Wu et al.
Drug metabolism and disposition: the biological fate of chemicals, 25(6), 768-771 (1997-06-01)
The blood-brain barrier (BBB) permeability to morphine and morphine-6-glucuronide (M6G) is measured under identical conditions using an intravenous injection method in the rat and HPLC separation of morphine from its metabolites. The brain uptake of M6G expressed as %ID/g was
E K Krzanowska et al.
Brain research, 799(2), 329-333 (1998-07-24)
The present study examined whether morphine and morphine-6beta-glucuronide (M6G) analgesia on the tail-flick and jump tests differed in potency in the periaqueductal gray, the locus coeruleus or the rostral ventromedial medulla. Morphine and M6G significantly and dose-dependently elicited analgesia on
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
Alexander T Nguyen et al.
European journal of pharmacology, 682(1-3), 86-91 (2012-03-01)
Previous studies have shown that morphine-6-glucuronide (M6G), a metabolite of morphine, induces reward and psychomotor stimulation but the role of the mu opioid receptor in these actions of the drug is not fully characterized. Thus, using mice lacking exon-2 of
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