Codeinone
Chemical compound
From Wikipedia, the free encyclopedia
Codeinone is an isoquinolone alkaloid[1] found in the opium poppy.[2] As an analgesic, it is one-third the potency of codeine. It is an important intermediate in the production of hydrocodone–a painkiller about three-quarters the potency of morphine[citation needed]–as well as of oxycodone,[3] though the latter can also be synthesized from thebaine.[4]
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| Names | |
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| IUPAC name
3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one | |
| Preferred IUPAC name
(4R,4aR,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-one | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.716 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H19NO3 | |
| Molar mass | 297.35 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical structure
Codeinone can be described as the methylether of morphinone: 3-methyl-morphinone.
Codeinone can be also described as the ketone of codeine: codeine-6-one.
Apoptotic activity
Through renewed interest into possible anti-tumor activities of some of the opium alkaloids and derivatives, unrelated to their antinociceptive properties and habit-forming effects, the oxidation product of codeine has been found to induce cell death in three different human cancer cell lines in vitro.[5]
