14-Hydroxycodeine


14-Hydroxycodeine also known as hydroxycodeine, is an toxic opioid, and also an alkaloid an organic compound that is a minor natural product found in some plants and bacteria and is an important intermediate in the synthesis of potent opioid analgesics such as oxycodone and other 14-hydroxylated opiate drugs. It is not used as a standalone drug and has no medical use. 14-Hydroxycodeine is an alkaloid component of the plant Papaver bracteatum.
Transformations occurring during bacterial oxidation of codeine by Streptomyces griseus: 14-hydroxycodeine and norcodeine were rigorously identified as products arising from codeine oxidation by Streptomyces griseus.

Toxicity

14-Hydroxycodeine is a hazardous substance, acute toxic substance upon ingestion and inhalation, causes skin sensitization and subsequent hypersensitivity to specific substances and severe allergic reactions. Possesses acute toxicity when inhaled or may cause allergy or asthma symptoms or breathing difficulties if inhaled.

Chemistry

14-Hydroxycodeine is an N-methyl-14-hydroxy derivative of codeine, where hydroxylation occurs at the carbon atom in position 14 of the morphinan skeleton.