3-Acetyloxymorphone

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3-Acetyloxymorphone

3-Acetyloxymorphone is a semi-synthetic opioid compound that is derived from thebaine, a naturally occurring alkaloid found in the opium poppy, Papaver somniferum. It is a potent analgesic, approximately 1.5 times more potent than morphine, its parent compound.

Chemistry

3-Acetyloxymorphone is a 3-acetyl derivative of oxymorphone. It is structurally similar to other opioids such as hydrocodone and hydromorphone, but it differs in the position and type of its functional groups. The compound has a molecular formula of C₁₉H₂₁NO₄ and a molecular weight of 327.37 g/mol.

Pharmacology

As an opioid, 3-acetyloxymorphone acts primarily on the mu-opioid receptor (MOR), which is responsible for the analgesic effects of opioids. It also has affinity for the kappa-opioid receptor (KOR) and the delta-opioid receptor (DOR), but to a lesser extent.

The compound is metabolized in the liver by the enzyme cytochrome P450 (CYP450), specifically the CYP3A4 and CYP2D6 isoforms. The primary metabolites of 3-acetyloxymorphone are 3-acetyl-6-glucuronide and 3-acetyl-3-glucuronide, both of which are excreted in the urine.

Clinical Use

3-Acetyloxymorphone is not currently approved for medical use in any country. However, it has been studied for its potential use in the treatment of severe pain. Its high potency and long duration of action make it a promising candidate for this indication.

Safety and Side Effects

Like all opioids, 3-acetyloxymorphone has the potential to cause a range of side effects. These can include nausea, vomiting, constipation, drowsiness, and respiratory depression. It also carries a risk of addiction and dependence, particularly with long-term use.

See Also

• Opioid
• Thebaine
• Oxymorphone
• Morphine
• Hydrocodone
• Hydromorphone