Oxycodone is an opioid analgesic medication synthesized from thebaine. It was developed in 1916 in Germany, as one of several new semi-synthetic opioids with several benefits over the older traditional opiates and opioids; morphine, diacetylmorphine (heroin) and codeine. It was introduced to the pharmaceutical market as Eukodal or Eucodal and Dinarkon. Its chemical name is derived from codeine - the chemical structures are very similar, differing only in that the hydroxyl group of codeine has been oxidized to a carbonyl group (as in ketones), hence the "-one" suffix, the 7,8-dihydro-feature (codeine has a double-bond between those two carbons), and the hydroxyl group at carbon-14 (codeine has just a hydrogen in its place), hence oxycodone.

In the United States, oxycodone is a Schedule II controlled substance both as a single agent and in combination with products containing paracetamol (aka acetaminophen), ibuprofen or aspirin.

Chemistry

Oxycodone sold legally is made from thebaine, an opiate alkaloid and minor component of opium.

The chemical structure of oxycodone is the methylether of oxymorphone: 3-methyl-oxymorphone. It could also be described as 14-hydroxy-7,8-dihydro-codeinone. It is principally supplied as its hydrochloride salt: oxycodone hydrochloride. The terephthalate salt of oxycodone is present in some formulations such as Percodan as 7.6 per cent of the weight of the oxycodone salts content of the product, viz. 5 mg of oxycodone in Percodan is 4.62 mg hydrochloride and 0.38 mg terephthalate. There does not appear to be a significant difference in the action of the salts. The hydrochloride-terephthalate mixture appears to be part of the original formulation of Percodan by its German manufacturers from more than 75 years ago.Fact: date=September 2007

Other oxycodone salts used around the world include phosphate, sulfate, pectinate, tartrate, bitartrate, citrate, and iodide.Fact: date=September 2007

Side effects

The most commonly reported effects include constipation, fatigue, dizziness, nausea, lightheadedness, headache, dry mouth,anxiety, pruritus, and diaphoresis. It has also claimed to cause dimness in vision due to miosis. Some patients have also experienced loss of appetite, nervousness, anxiety, euphoria, abdominal pain, diarrhea, dyspnea, and hiccups, although these symptoms appear in less than 5% of patients taking oxycodone. Rarely, the drug can cause impotence, enlarged prostate gland, and decreased testosterone secretion.

In high doses, overdoses, or in patients not tolerant to opiates, oxycodone can cause shallow breathing, bradycardia, cold, clammy skin, apnea, hypotension, pupil constriction, circulatory collapse, respiratory arrest, and death.