Codeinone
Codeinone is 1/3 as active as codeine as an analgesic but it is an important intermediate in the production of hydrocodone, a painkiller about 3/4 the potency of morphine; as well as of oxycodone.[1] The latter can also be synthesized from thebaine, however.[2]
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| IUPAC name
(5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one | |
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3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.716 |
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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| Infobox references | |
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.[3]
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References
- Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
- Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
- Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543
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