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
467-13-0 N
ChEBI CHEBI:18399 YesY
ChEMBL ChEMBL257627 YesY
ChemSpider 4573639 YesY
Jmol-3D images Image
PubChem 5459910
Properties
C18H19NO3
Molar mass 297.35 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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, a painkiller roughly half again more or up to 1.7× the strength of morphine.[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