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
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 | |
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ChemSpider | |
ECHA InfoCard | 100.006.716 |
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Properties | |
Chemical formula |
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.[3]
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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