Codeinone is an isoquinolone alkaloid found in the opium poppy. 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, though the latter can also be synthesized from thebaine.
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
"codeinone (CHEBI:18399)". www.ebi.ac.uk. Retrieved 28 October 2023. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18399 ↩
Lenz, Rainer; Zenk, Meinhart H. (April 1995). "Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum". Tetrahedron Letters. 36 (14): 2449–2452. doi:10.1016/0040-4039(95)00278-K. /wiki/Doi_(identifier) ↩
Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005 https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html ↩
Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117 https://www.scribd.com/doc/77193676/Oxycodone-Synthesis ↩
Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543 /wiki/PMID_(identifier) ↩