Chemistry
Oxymorphone is commercially produced from thebaine, which is a minor constituent of the opium poppy (Papaver somniferum) but thebaine is found in greater abundance (3%) in the roots of the oriental poppy (Papaver orientale). Oxymorphone can also be synthesized from morphine or oxycodone, and is an active metabolite of the latter drug. The structure-activity relationship of oxymorphone and its derivatives has been well-examined. Esterification of the hydroxyl groups yields stronger compounds. Another derivative of oxymorphone is the opioid antagonist naloxone (Narcan).
As reported in the July 1993 issue of Applied Environmental Bacteriology (PDF available at http://aem.asm.org/cgi/reprint/61/10/3645.pdf), the bacterium Pseudomonas putida, serotype M10 turns oxymorphone into oxymorphol by means of a one-step conversion involving morphine dehydrogenase and a naturally occurring NADH-dependent morphinone reductase that can work on unsaturated 7,8 bonds.
German patents from the middle 1930s indicate that oxymorphone as well as hydromorphone, hydrocodone, oxycodone, and acetylmorphone can be prepared—without the need for hydrogen gas—from solutions of codeine, morphine, and dionine by refluxing an acidic aqueous solution, or the precursor drug dissolved in ethanol, in the presence of Column 7 metals, namely palladium and platinum in fine powder or colloidal form or platina black. It is unclear from information available if aluminium or nickel can be used as a catalyst in these reactions as well.
However, the aforementioned patents deal specifically with hydrogenation reactions producing dihydrocodeinone (hydrocodone), dihydromorphinone (hydromorphone), and ethyldihydromorphinone as final products. Hence it is unclear at best and rather unlikely that these particular procedures can be applied for the synthesis of oxycodone or oxymorphone, as they are not typically synthesized in this manner.
The rare practise of making homebake oxymorphone generally uses oxycodone and pyridine amongst others, and the production of homebake hydromorphone (Dilaudid) from hydrocodone does also exist but is extremely rare. This is similar to a method especially common in New Zealand to make morphine out of codeine. The resultant morphine base is used as is, made into a salt (usually citrate, although ascorbate, acetate, hydrochloride, nitrate, phosphate, and sulphate are also possible) by dissolving the base in a solution containing the relevant acid, or treated with acetic anhydride or rarely other chemicals capable of acetylating compounds to produce what is usually a mixture of heroin, morphine, 3-monoacetylmorphine and 6-monoacetylmorphine. Depending on the method, this can also contain acetylcodeine and leftover codeine.
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—Ralph Waldo Emerson (1803–1882)
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