Codeinone

Codeinone

Codeinone is an organic compound and a specific type of opiate that is primarily used in the production of codeine and hydrocodone. It is a secondary metabolite of the opium poppy (Papaver somniferum) and is chemically classified as a phenanthrene alkaloid.

Chemical Structure and Properties

Codeinone is a member of the class of compounds known as morphinans, which are polycyclic compounds with a skeleton based on the morphinan system. It has a molecular formula of C18H21NO3 and a molecular weight of 297.365 g/mol. The compound is characterized by a double bond between the carbon atoms at positions 7 and 8 and a ketone group at position 6.

Biosynthesis

The biosynthesis of codeinone involves several enzymatic steps. The process begins with the conversion of thebaine, another opiate alkaloid, into codeinone. This reaction is catalyzed by the enzyme thebaine 6-O-demethylase (T6ODM) and involves the removal of a methyl group from thebaine. The resulting compound, codeinone, can then be reduced to codeine by the enzyme codeine O-demethylase (CODM).

Uses

Codeinone is primarily used as a precursor in the production of codeine and hydrocodone, two commonly used pain relievers. Codeine is also used as a cough suppressant and is often combined with other medications in cough and cold remedies. Hydrocodone, on the other hand, is a semi-synthetic opioid that is used to treat moderate to severe pain.

Safety and Regulation

Due to its use in the production of opioids, codeinone is regulated under the Controlled Substances Act in the United States and similar legislation in other countries. It is classified as a Schedule II controlled substance, meaning it has a high potential for abuse and can lead to severe psychological or physical dependence.

See Also

• Morphine
• Opioid
• Thebaine

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