3,14-Diacetyloxymorphone

A semi-synthetic opioid analgesic

3,14-Diacetyloxymorphone
3,14-Diacetyloxymorphone.svg
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number
PubChem
DrugBank
ChemSpider
KEGG

3,14-Diacetyloxymorphone is a semi-synthetic opioid analgesic derived from oxymorphone. It is chemically related to other opioids such as morphine and heroin.

Chemical Structure

3,14-Diacetyloxymorphone is an acetylated derivative of oxymorphone, with acetyl groups at the 3 and 14 positions of the morphinan skeleton. This modification increases its lipophilicity, potentially enhancing its ability to cross the blood-brain barrier.

Pharmacology

As an opioid, 3,14-Diacetyloxymorphone acts primarily on the mu-opioid receptor, producing effects such as analgesia, euphoria, and respiratory depression. Its potency and efficacy are influenced by its chemical structure, which affects its binding affinity and intrinsic activity at opioid receptors.

Synthesis

The synthesis of 3,14-Diacetyloxymorphone involves the acetylation of oxymorphone. This process typically uses acetic anhydride as the acetylating agent in the presence of a catalyst or under specific conditions to ensure selective acetylation at the desired positions.

Medical Use

While 3,14-Diacetyloxymorphone itself is not commonly used in clinical practice, its parent compound, oxymorphone, is used for the management of moderate to severe pain. The acetylated derivative may have been studied for its pharmacokinetic properties or potential as a prodrug.

Legal Status

Due to its structural similarity to other controlled opioids, 3,14-Diacetyloxymorphone is likely to be regulated under similar legal frameworks. It may be classified as a controlled substance in many jurisdictions, subject to restrictions on its manufacture, distribution, and use.

Related pages

• Oxymorphone
• Opioid
• Morphine
• Heroin

• 3,14-Diacetyloxymorphone
  3,14-Diacetyloxymorphone