Codeinone
| Codeinone | |
|---|---|
| [[File:|frameless|220px|alt=|Chemical structure of Codeinone]] | |
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| CAS Number | 467-15-2 |
| PubChem | 5462328 |
| DrugBank | |
| ChemSpider | 4576620 |
| KEGG | |
Codeinone is a naturally occurring opiate alkaloid and a derivative of codeine. It is classified as a morphinan and is structurally related to morphine and thebaine. Codeinone is an intermediate in the biosynthesis of codeine and morphine in the opium poppy, Papaver somniferum.
Chemical Structure and Properties
Codeinone has the chemical formula C18H19NO3 and a molecular weight of 297.35 g/mol. It is characterized by the presence of a 6-keto group, distinguishing it from codeine, which has a 6-hydroxy group. The presence of the 6-keto group makes codeinone more reactive and a key intermediate in the conversion of codeine to morphine.
Biosynthesis
In the opium poppy, codeinone is synthesized from thebaine through a series of enzymatic reactions. The conversion involves the action of the enzyme thebaine 6-O-demethylase, which demethylates thebaine to produce codeinone. Subsequently, codeinone is reduced to codeine by the enzyme codeinone reductase.
Pharmacology
Codeinone itself is not used therapeutically, but it is an important intermediate in the synthesis of other opiates. Its pharmacological properties are similar to those of other morphinans, but it is primarily of interest for its role in the biosynthetic pathway of more clinically relevant opiates.
Synthesis and Derivatives
In addition to its natural occurrence, codeinone can be synthesized in the laboratory from codeine or thebaine. It serves as a precursor for the synthesis of various semi-synthetic opiates, including oxycodone and hydrocodone.
Research and Applications
Research into codeinone focuses on its role in the biosynthesis of opiates and its potential use in the development of new analgesics. Understanding the enzymatic pathways that convert codeinone to other opiates can aid in the development of novel pain management therapies.
Also see
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