Codeinone Explained

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–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]

Notes and References

1. Web site: codeinone (CHEBI:18399) . www.ebi.ac.uk . 28 October 2023.
2. Lenz . Rainer . Zenk . Meinhart H. . Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum . Tetrahedron Letters . April 1995 . 36 . 14 . 2449–2452 . 10.1016/0040-4039(95)00278-K.
3. https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html Synthesis of Oxycodone from Codeine.
4. https://www.scribd.com/doc/77193676/Oxycodone-Synthesis Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate.
5. Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76.