Morphine oxide

Chemical studies on drug metabolism. IV. Synthesis and analgesic activity of morphine-7,8-oxide and heroin-7,8-oxide... 

An alkaloid pain reliever, morphine, is an often abused drug. Chronoampero-metric MIP chemosensors have been devised for its determination [204]. In these chemosensors, a poly(3,4-ethylenedioxythiophene) (PEDOT) film was deposited by electropolymerization in ACN onto an ITO electrode in the presence of the morphine template to serve as the sensing element [204], Electrocatalytic current of morphine oxidation has been measured at 0.75 V vs AglAgCllKClsat (pH = 5.0) as the detection signal. A linear dependence of the measured steady-state current on the morphine concentration extended over the range of 0.1-1 mM with LOD for morphine of 0.2 mM. The chemosensor successfully discriminated morphine and its codeine analogue. Furthermore, a microfluidic MIP system combined with the chronoamperometric transduction has been devised for the determination of morphine [182] with appreciable LOD for morphine of 0.01 mM at a flow rate of 92.3 pL min-1 (Table 6). 

Molecular weight 301.33 (301.13) Synonyms Genomorphine morphine oxide... 

Morphin sensors based on MIPs have also been described [432,439,441]. Amperometric morphine sensors based on morphin imprinted poly(3,4-ethylene-dioxythiophene), which catalyze morphine oxidation and lowers the oxidization potential on an indium tin oxide (ITO) electrode, is an example. The same MIP has been used in the form of immobilized molecular particles for the same purpose. In one report, rather uniform MIP microspheres were prepared through precipitation polymerization to produce more active surface area. Poly(3,4-ethylenedioxythiophene) was utilized to immobilize the MIP particles, prepared through the reaction between methacrylic acid monomers and trimethylolpropane trimethacrylate crossHnkers in the presence of morphin, on indium tin oxide (ITO) glass [441]. Another microfluidic amperometric MIP-based morphin sensing system, using 3,4-ethylenedioxythiophene monomers, has also been reported in the literature [439]. 

Papaver somniferum.- Rapoport and Hodges have obtained from this species an enzyme which catalyzes the reduction of codeinone to codeine, in the presence of NADH as a coenz3nne. Another enzyme, partially purified by centrifugal fractionation, was obtained which catalyzed the oxidative coupling of the phenolic rings of reticuline to yield the dienone salutaridine . Hydrogen peroxide was utilized by this enzyme for the oxidation. A crude enzyme from this species converted morphine to the dimeric pseudomorphine and morphine -oxide . ... 

Hydromorphone [466-99-9] (31) and hydrocodone [125-29-1] (32) are isomers of morphine and codeine, respectively. Hydromorphone can be prepared by catalytic rearrangement of morphine (49) or by oxidation of the aliphatic hydroxyl group of dihydromorphine (50). Hydrocodone can be similarly prepared. As an antitussive, hydromorphone is several times more active than morphine and hydrocodone is slightly more active than codeine. Hydromorphone has a much higher addiction potential than hydrocodone. 

Morphine and heroin form fluorescent oxidation products on heating in the presence of ammonia [1]. 

Small and Paris m have prepared the isomeric 4-morphines by the gentle oxidation of a-, and y-isomorphines (p. 218). They can all be represented by the formula, Cj agOgNa. 3HaO, and their chief characteristics are as follows —... 

The three alkaloids concerned, morphine, codeine and thebaine, all behave as tertiary bases. Morphine contains two hydroxyl groups of which one is phenolic and the other a secondary alcohol group. On methylation of the phenolic hydroxyl codeine results. On oxidation, codeine is transformed into codeinone by conversion of the secondary alcohol group into a carbonyl group, and when thebaine is boiled with A-sulphuric acid for a few minutes, it is hydrolysed into codeinone and methyl sulphate, and in other ways thebaine has been shown to contain two methoxyl groups. That the relationship between the three alkaloids is close may be illustrated by the following slightly extended formula —... 

Considerable progress has also been made with the alternative line of work, the search for a synthetic analgesic as effective as morphine and without its disadvantages. The work of the American Committee has shown that it is possible to produce analgesics with a dibenzofuran or carbazole nucleus in place of the phenanthrene or phcnanthrylene oxide nucleus of morphine and it is stated that synthetic products with analgesic potency equal to that of codeine have been prepared. In the 1938 report moderate analgesic potency was recorded for preparation No. 421, 9-methyl-2-(l-hydroxy-3-diethylamino)-propylcarbazole at 10 mgm. by injection. 

When morphine is subjected to a similar reduction-oxidation sequence (1- 10), there is obtained hydromorphone (10). ... 

Although this isoquinoline at first bears little structural resemblance to morphine (108), careful rearrangement of the structure (A) shows the narcotic to possess the benzylisoquinoline fragment within its framework. Indeed, research on the biogenesis of morphine has shown that the molecule is formed by oxidative coupling of a phenol closely related to papaverine. 

Hynes MD, Berkowitz BA Catecholamine mechanisms in the stimulation of mouse locomotor activity hy nitrous oxide and morphine. Eur J Pharmacol 90 109-114, 1983... 

A new strategy for the syntheas of oxide-containing fragments of morphine has been developed. Thus, the tricyclic (ANO) morphine fragment 45 was obtained as the sole product via an intramolecular radical cyclization. The tetracyclic (ACNO) fragment 46 was synthesized in a similar fashion starting from 5,6,7,8-tetrahydroisoquinoline <96T10935>. 

Perez-Casanova A, Noel RJ Jr, Rivera-Amill V, Husain K, Kumar A (2007) Morphine-mediated deterioration of oxidative stress leads to rapid disease progression in SIV/SHIV-infected macaques. AIDS Res Hum Retroviruses 23 1004-1007 Persidsky Y, Gendelman HE (2003) Mononuclear phagocyte immunity and the neuropathogenesis of HIV-1 infection. J Leukoc Biol 74 691-701... 

Morphine and HlV-Tat increase nucrogUal-free radical production and oxidative stress possible role in cytokine regulation. J Neurochem 108 202-215... 

The oxidation of morphine by Pseudomonas putida MIO gave rise to a large number of transformation products including hydromorphone (dihy-dromorphinone), 14/3-hydroxymorphine, 14 6-hydroxymorphinone, and dihydromorphine. Similarly, in incubations with oxymorphone (14/3-hydroxy-... 

Schemes Transformation steps involved in the oxidation of morphine by incubation with Pseudomonas putida MIO, which gave hydromorphone (dihydromorphinone), 14 d-hydroxymorphine, 14 8-hydroxymorphinone, and dihydromorphine [52]...

The oxidation of morphine by whole-cell suspensions and cell extracts of Cylindrocarpon didymum gave rise to the formation of 2,2 -bimorphine (for structure, see Fig. 6). The identity of 2,2 -bimorphine was confirmed by clas-... 

Scheme 4 The initial steps in the metaholism of morphine and codeine hy Pseudomonas putida MIO involved in the oxidation process...

Stabler PJ, Bruce NC (1998) Oxidation of morphine to 2,2 -bimorphine by cylindro-carpon didymum. Appl Environ Microbiol 64(10) 4106-4108... 

Morphine -ferrocene reduction/oxidation of label decreased... 

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