With a formula of C17H19NO3 and a molecular weight of 285.343, both identical to morphine,<unk>  can be considered a structural isomer of morphine and is a hydrogenated ketone thereof.<unk>  is made from morphine either by direct re-arrangement (made by reflux heating of alcoholic or acidic aqueous solution of morphine in the presence of platinum or palladium catalyst) or reduction to dihydromorphine (usually via catalytic hydrogenation), followed by oxidation with benzophenone in presence of potassium tert butoxide or aluminium tert butoxide (Oppenauer oxidation). The 6 ketone group may be replaced with a methylene group via the Wittig reaction to produce 6-Methylenedihydrodesoxymorphine, which is 80× stronger than morphine. Changing morphine into<unk>  increases its activity and, therefore, makes<unk>  approximately eight times stronger than morphine on a weight basis, all other things being equal. Changed also is lipid solubility, contributing to<unk> 's having a more rapid onset of action and alterations to the overall absorption, distribution, metabolism, and elimination profile as well as the side effect profile (in general, less nausea and itching) versus that of morphine. The semi-synthetic opiates, of which<unk>  and its codeine analogue hydrocodone are among the best-known and oldest, include a huge number of drugs of varying strengths and with differences among themselves both subtle and stark, allowing for many different options for treatment.<unk>  is more soluble in water than morphine; therefore,<unk>  solutions may be produced to deliver the drug in a smaller volume of water. The hydrochloride salt is soluble in three parts of water, whereas a gram of morphine hydrochloride dissolves in 16 ml of water; for all common purposes, the pure powder for hospital use can be used to produce solutions of virtually arbitrary concentration. When the powder appeared on the street, this very small volume of powder needed for a dose means that overdoses are likely for those who mistake it for heroin or other powdered narcotics, especially those that have been diluted prior to consumption. Endogenous production<unk>  is made from morphine via catalytic hydrogenation and also is produced in trace amounts by human and other mammalian metabolisms of morphine. It occasionally appears in assays of opium latex in very small quantities, apparently forming in the plant in an unknown percentage of cases under poorly understood conditions. Bacteria Some bacteria have been shown to be able to turn morphine into closely related drugs, including<unk>  and dihydromorphine among others. The bacterium Pseudomonas putida serotype M10 produces a naturally-occurring NADH-dependent morphinone reductase that can work on unsaturated 7,8 bonds, with result that, when these bacteria are living in an aqueous solution containing morphine, significant amounts of<unk>  form, as it is an intermediary metabolite in this process; the same goes for codeine being turned into hydrocodone. The process gave rise to various concentrations of<unk> , dihydromorphine, hydromorphinol, and oxymorphone during the experiments. Three paths were found: from morphine to<unk>  with dihydromorphine as the penultimate step, from morphine to<unk>  with morphinone as the penultimate step, and from morphine to hydromorphinol to<unk> .
Hydromorphone
Oxymorphone
Morphine
Nalorphine
Ropivacaine
Butorphanol
Oxymorphol
Sufentanil