Codeinone

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Codeinone
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Molar mass 297.35 g/mol

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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 morphineScript error: No such module "Unsubst".–as well as of oxycodone,[3] though the latter can also be synthesized from thebaine.[4]

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]

References

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  3. Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
  4. Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
  5. Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. Template:Catalog lookup link

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