20290-09-9

Basic information

• Product Name: M-3-G HYDRATE
• Synonyms: M-3-G HYDRATE;MORPHINE-3-BETA-D-GLUCURONIDE;MORPHINE-3-BETA-D-GLUCURONIDE HYDRATE;MORPHINE-3-GLUCURONIDE;morphine-3-B-D-glucuronide*methanol solution;morphine-3-B-D-glucuronide--dea*schedule ii item;MORPHINE-3-B-D-GLUCURONIDE MAJOR METABOL ITE OF M;(5a,6a)-7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl b-d-Glucopyranosiduronic Acid
• CAS NO: 20290-09-9
• Molecular Formula: C23H27NO9
• Molecular Weight: 461.46
• Product Categories: Glucuronides;Intermediates & Fine Chemicals;Pharmaceuticals;Controlled Drug StandardsAlphabetic;METI - MZDrugs of Abuse;AlkaloidsStable Isotopes;Chemical Structure;Drugs of Abuse;M;Morphine;Heterocycles;Metabolites & Impurities
• Mol File: 20290-09-9.mol

Chemical Properties

• Melting Point: 220-224°C
• Boiling Point: 745.1 ºCat 760 mmHg
• Flash Point: 11 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 2.58E-23mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: 2-8°C
• PKA: pKa 2.88 ± 0.01;8.21± 0.11(H2O,t =25,I=0.154(KCl))(Approximate)
• CAS DataBase Reference: M-3-G HYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: M-3-G HYDRATE(20290-09-9)
• EPA Substance Registry System: M-3-G HYDRATE(20290-09-9)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 23/25-36/38-36-20/21-61-43-22-39/23/24/25-23/24/25-10-11
• Safety Statements: 36-45-53-36/37-16-7
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 20290-09-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
M-3-G HYDRATE is used as a pharmaceutical ingredient for its humectant properties, which helps in retaining moisture and preventing the drying out of the skin. It is commonly used in the formulation of various medications, including cough syrups, elixirs, and liquid medications, as it helps in maintaining the stability and consistency of the formulations.
Used in Cosmetics and Personal Care Industry:
M-3-G HYDRATE is used as a humectant in cosmetics and personal care products, such as lotions, creams, and shampoos, to help retain moisture and improve the texture and feel of the products. It also acts as an emollient, providing a smooth and soft texture to the skin and hair.
Used in Food and Beverage Industry:
M-3-G HYDRATE is used as a humectant in the food and beverage industry to retain moisture and improve the texture and shelf life of various products, such as baked goods, confectionery, and beverages. It also acts as a sweetening agent and a thickening agent in certain food products.
Used in Industrial Applications:
M-3-G HYDRATE is used in various industrial applications, such as in the manufacturing of resins, inks, and dyes, as well as in the production of biodiesel and other biofuels. It also serves as a solvent for various chemicals and pharmaceuticals.
Used as a Controlled Substance:
M-3-G HYDRATE is considered a controlled substance due to its analog properties with morphine, a potent opioid analgesic. It exhibits unexpected lipophilicity, which may contribute to its potential for abuse and addiction.

InChI:InChI=1/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

Upstream product

• 57-27-2 MORPHIN 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 2616-64-0 UDP-glucuronic acid 
• 78132-48-6 uridine-diphosphate-glucuronic acid triammonium salt 
• 106262-09-3 7,8-didehydro-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 3,6-dibenzoate 
• 106262-11-7 7,8-didehydro-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3,6-diol 6-benzoate 

Relevant articles and documents

Synthetic method of morphine derivative and applications

The invention discloses a synthetic method of a morphine derivative. The method employs morphine as an initial raw material, and selective protection and glycosylation are carried out in order to obtain a target product. The HPLC purity of M3G obtained by the synthetic method reaches 99.8%, and the M3G can be used as a reference substance or a standard substance for researching quality of relatedproducts.

Glucuronidation of paracetamol by human liver microsomes in vitro: Enzyme kinetic parameters and interactions with short-chain aliphatic alcohols and opiates

In this study, glucuronidation of paracetamol (CAS 103-90-2) by human liver microsomes and the effects of aliphatic alcohols and opiates were investigated. Paracetamol glucuronidation was optimised for various incubation conditions. Ten different aliphatic alcohols and the opiates morphine, codeine and dihydrocodeine were analysed as inhibitors of paracetamol glucuronidation. Furthermore, the effects of paracetamol on morphine-3 and codeine glucuronidation were investigated. Enzyme kinetic analysis was carried out via determination of the parameters Km, Vmax, Ki and the type of inhibition. Except for methanol and ethanol, all investigated alcohols inhibited glucuronidation of paracetamol. Ki values ranged between 4.59 mmol/l (n-pentanol) and 340.54 mmol/l (2-propanol). Extent of inhibition strongly depended on the structure and clearly increased with the length of the alkyl chain. All tested opiates inhibited paracetamol glucuronidation with Ki values between 4.02 mmol/l (dihydrocodeine) and 11.44 mmol/l (morphine). Paracetamol itself turned out to be an inhibitor of opiate glucuronidation. The apparent Ki values were 4.62 mmol/l (inhibition of morphine-3 glucuronidation) and 9.44 mmol/l (inhibition of codeine glucuronidation). A mixed inhibition type was determined for all substances. The in vitro studies show a great inhibition potential for the analysed substances. Transferring the results to the in vivo situation, a higher liver toxicity of paracetamol can be assumed, if concomitantly a lot of alcoholic beverages with congener alcohols - e.g. fruit schnapps or whisky - are drunk or if opiates - as analgesics or narcotics - are taken in higher doses. ECV Editio Cantor Verlag.

Glucuronidation in the chimpanzee (Pan troglodytes): Studies with acetaminophen, oestradiol and morphine

The chimpanzee has recently been characterized as a surrogate for oxidative drug metabolism in humans and as a pharmacokinetic model for the selection of drug candidates. In the current study, the glucuronidation of acetaminophen, morphine and oestradiol was evaluated in the chimpanzee to extend the characterization of this important animal model. Following oral administration of acetaminophen (600 mg) to chimpanzees (n = 2), pharmacokinetics were comparable with previously reported human values, namely mean oral clearance 0.91 vs. 0.62 ± 0.05 l h-1 kg-1, apparent volume of distribution 2.29 vs. 1.65 ± 0.25 l kg-1, and half-life 1.86 vs. 1.89 ± 0.27 h, for chimpanzee vs. human, respectively. Urinary excretions (percentage of dose) of acetaminophen, acetaminophen glucuronide and acetaminophen sulfate were also similar between chimpanzees and humans, namely 2.3 vs. 5.0, 63.1 vs. 54.7, and 25.0 vs. 32.3%, respectively. Acetaminophen, oestradiol and morphine glucuronide formation kinetics were investigated using chimpanzee (n = 2) and pooled human liver microsomes (n = 10). V maxapp and Kmapp (or S 50app) for acetaminophen glucuronide, morphine 3- and 6-glucuronide, and oestradiol 3- and 17-glucuronide formation were comparable in both species. Eadie-Hofstee plots of oestradiol 3-glucuronide formation in chimpanzee microsomes were characteristic of autoactivation kinetics. Western immunoblot analysis of chimpanzee liver microsomes revealed a single immunoreactive band when probed with anti-human UGT1A1, anti-human UGT1A6, and anti-human UGT2B7. Taken collectively, these data demonstrate similar glucuronidation characteristics in chimpanzees and humans.

A highly toxic morphine-3-glucuronide derivative

By the coupling of octylamine to the uronic acid function of morphine-3-glucuronide (M3G) a new glycoconjugate (morphine-3- octylglucuronamide, M3GOAM) was prepared. When assayed in both rats and mice up to ng/kg (ip) doses none of the animals survived. The aliphatic octyl chain may be the lethal factor since a closely related derivative (M3GNH2), was not toxic and showed similar opioid antagonist properties than naloxone.

Morphine 6-Glucuronide and Morphine 3-Glucuronide as Molecular Chameleons with Unexpected Lipophilicity

Morphine 6-glucuronide, but not morphine 3-glucuronide, is a highly potent opiate receptor agonist.In fact, there is converging evidence that much of the analgesic effect occurring after morphine treatment in humans is due to this metabolite rather than to the parent drug.Yet glucuronides as a rule are considered as highly polar metabolites unable to cross the blood-brain barrier and rapidly excreted by the urinary and/or biliary routes.Here, we report that morphine 6-glucuronide, and to a lesser extent morphine 3-glucuronide, are far more lipophilic than predicted, and in fact not much less lipophilic than morphine itself.Force-field and quantum mechanical calculations indicate that the two glucuronides can exist in conformational equilibrium between extendend and folded forms.The extended conformers, because they efficiently expose their polar groups, must be highly hydrophilic forms predominating in polar media such as water; in contrast, the folded conformers mask part of their polar groups, thus being more lipophilic and likely to predominate in media of low polarity such as biological membranes.