Codeine
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Codeine is an opiate used in the treatment of pain and to reduce coughing. It occurs naturally in the opium poppy and as such has a long history of human use.
Chemical name
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy- 17-methylmorphinan-6-ol
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| Codeine
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| Systematic (IUPAC) name | |
| (5α,6α)-7,8-didehydro-4,5-epoxy- 3-methoxy-17-methylmorphinan-6-ol | |
| Identifiers | |
| CAS number | |
| ATC code | R05 N02 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C18H21NO3 |
| Mol. mass | 299.364 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ~90% Oral |
| Metabolism | Hepatic, via CYP2D6 (Cytochrome P450 2D6)[1] |
| Half life | 2.5–3 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Controlled (S8)(AU) Schedule I(CA) Class B(UK) Schedule II(US) |
| Routes | oral, intra-rectally, SC, IM |
History
Codeine is an alkaloid found in opium and other poppy saps like Papaver bracteatum, the Iranian poppy, in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. It was first isolated in 1830 in France by Jean-Pierre Robiquet.
The effects of the Nixon War On Drugs by 1972 or so had caused across-the-board shortages of illicit and licit opiates because of a scarcity of natural opium, poppy straw and other sources of opium alkaloids, and the geopolitical situation was getting less helpful for the United States. After a large percentage of the opium and morphine in the US National Stockpile of Strategic & Critical Materials had to be tapped in order to ease severe shortages of medicinal opiates -- the codeine-based antitussives in particular -- in late 1973, researchers were tasked with and quickly succeeded in finding a way to synthesize codeine and its derivatives and precursors from scratch from petroleum or coal tar using a process developed at the United States' National Institutes of Health.
Numerous codeine salts have been prepared since the drug was discovered. The most commonly used are the hydrochloride (freebase conversion ratio 0.805), phosphate (0.736), sulphate (0.859) and citrate (0.842). Others include a salicylate NSAID, codeine salicylate (0.686), and at least four codeine-based barbiturates, the cyclohexenylethylbarbiturate (0.559), cyclopentenylallylbarbiturate (0.561), diallylbarbiturate (0.561), and diethylbarbiturate (0.619).
Other names
- Tylenol with Codeine
- Codate
- Codephos
- Codamol
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