3-methoxymorphinan

3-Methoxymorphinan is a chemical compound that belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene "moiety", one of which is aromatic while the two others are alicyclic.

Chemical Structure

The chemical structure of 3-Methoxymorphinan consists of a morphinan core, which is a tricyclic structure containing a phenanthrene (three-ring) core, with a methyl substituent at the 3-position and a methoxy group at the 17-position.

Pharmacology

3-Methoxymorphinan is a metabolite of dextromethorphan, a common ingredient in over-the-counter cough suppressants. It is produced in the body by the action of the enzyme CYP2D6, which metabolizes dextromethorphan to 3-methoxymorphinan. This metabolite has been found to have antitussive (cough-suppressing) effects, similar to its parent compound.

Clinical Significance

The presence of 3-Methoxymorphinan in urine can be used as a biomarker for dextromethorphan use or abuse. It can also be used to determine whether an individual is a poor or extensive metabolizer of dextromethorphan, based on the ratio of dextromethorphan to 3-methoxymorphinan in the urine.

See Also

• Dextromethorphan
• Morphinan
• CYP2D6
• Antitussive