Codeinone

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Codeinone
Codeinone.svg
Names
IUPAC name
(5α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.716
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).
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Infobox references

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;[citation needed] as well as of oxycodone.[1] The latter can also be synthesized from thebaine, however.[2]

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.[3]

References[edit]

  1. ^ Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
  2. ^ Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
  3. ^ Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543