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Synthesis of morphine 6-??-D-glucuronide - …

Elderly people in general have increased fat-to-lean body mass ratiosand reduced glomerular filtration rates. Opioids produce cognitive andneuropsychiatric dysfunction through poorly defined mechanisms that inpart include the accumulation of biologically active metabolites such asmorphine-6-glucuronideor normeperidine Opioid dosagetitration should take into account not only analgesic effects but alsoside effects that extend beyond cognitive impairment. Such side effectsmay include urinary retention (a threat in elderly males with prostatichyperplasia), constipation and intestinal obstruction, or respiratorydepression.

Morphine-6-glucuronide synthesis - Cenes Limited

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.

Induction of morphine-6-glucuronide synthesis by …

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.

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.

normorphine-6-glucuronide was synthesized by ..

The synthesis of morphine-3,6-di-β-D-glucuronide as the monolithium salt from a fully protected morphine-6-β-D-glucuronide 12 via selective 3-deacetylation followed by Lewis acid-catalyzed 3-glucuronidation, and stepwise deprotection with lithium hydroxide is described.

The first synthesis of three glucuronides of narcotics was reported. Codeine glucuronide (Va) was prepared by the condensation of codeine (Ia) with acetobromo sugar derivative (II) in the presence of silver carbonate and the following removal of the protecting groups by solvolysis and hydrolysis with sodium methoxide and aq. barium hydroxide, respectively. Morphine-6-glucuronide (Vb) was synthesized similarly to Va utilizing 3-acetyl-morphine (Ib) as the starting material. Morphine-3-glucuronide (VIII) was prepared by the condensation of morphine (VI) with II in sodium hydroxide-acetone. In this reaction, the intermediate derivative (VII) was not obtained but hydrolyzed to the free glucuronide (VIII).

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  • A Simple Synthesis of Morphine-3,6-di-b-dd-glucuronide Richard T

    24/01/2017 · Synthesis and analgesic effect of normorphine-3- and -6 ..

  • Synthesis of [l-3H]morphine-6-beta-D-glucuronide | RTI

    Morphine 6-glucuronide and morphine 3-glucuronide as molecular chameleons with unexpected lipophilicity

  • Process for making morphine-6-glucuronide or …

    Synthesis and biological evaluation of analogues of M6G.

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Synthesis and biological evaluation of analogues of M6G

The invention provides a method for the preferential synthesis of the beta-anomer of M6G which includes the step shown in Scheme 6: wherein use of DMAP is optional.

Morphine-6-β-D-glucuronide-D3 solution ..

In order to synthesise M6G the major problem to overcome is to obtain the glycoside linkage with very high beta-selectivity since prior methods produce the alpha-anomer.

Morphine-6-glucuronide - Pharmacodia

Nalorphine-3- and -6-glucuronide were synthesized according to the method used in the synthesis of morphine glucuronides. These glucuronides were then utilized as reference standards for identification of the urinary metabolites of nalorphine in rabbits, and nalorphine-3-glucuronide was established as a major metabolite. No other metabolite could be detected in the 24 hr urine samples, except a small amount of unchanged nalorphine was detected. Isolation procedure of the urinary glucuronides adopted in the present and previous studies was confirmed to be very effective especially for the morphine alkaloids.

Home > All Drugs > Morphine-6-glucuronide

Cancer often occurs in the elderly, who usually have decreased renalfunction as a normal result of aging. Mild age-related renalinsufficiency (decline in glomerular filtration rate) can impede theexcretion of the biologically active metabolites of many opioids,resulting in clinically significant sedation and respiratory depression as well asnausea Meperidine, methadone, levorphano, pentazocine, and propoxyphene haveincreased bioavailability, prolonged half-lives, and decreased systemicclearance and thus accumulate in patients with hepatic or renaldysfunction. Renal excretion is a major route of elimination not onlyfor opioids but also for their pharmacologically active metabolitesnorpropoxyphene, normeperidine, morphine-6-glucuronide, anddihydrocodeine. Hence, in patients with renal dysfunction, doses of theparent compounds should be lowered or given less frequently.

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