Codeinone
From Wikipedia the free encyclopedia
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| Names | |
|---|---|
| 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 | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.716 |
| KEGG | |
PubChem CID | |
| 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). | |
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[citation needed]–as well as of oxycodone,[3] though the latter can also be synthesized from thebaine.[4]
Chemical structure
[edit]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
[edit]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
[edit]- ^ "codeinone (CHEBI:18399)". www.ebi.ac.uk. Retrieved 28 October 2023.
- ^ 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.
- ^ 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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