Dextromethorphan

January 06, 2014
Image of Dextromethorphan 3D Image of Dextromethorphan

Dextromethorphan is a commonly used cough suppressant. It is the dextrorotatory form of the racemic racemethorphan, which was patented by Hoffmann-La Roche in 1954. O. Häfliger and co-workers prepared the chiral form in 1956. Dextromethorphan is an over-the-counter drug formulated most often as the hydrobromide monohydrate.

At high doses, dextromethorphan is a dissociative hallucinogen. Its effects are similar to those of phencyclidine (“angel dust”).

Recently, the combination of dextromethorphan and quinidine was shown to alleviate the symptoms of pseudobulbar affect: laughing and crying in patients with multiple sclerosis, amyotrophic lateral sclerosis, and other neurologic diseases. The combination drug was approved for this use by the US Food and Drug Administration in 2010. It is marketed by Avanir under the trade name Nuedexta.

MOTW update:
December 19, 2022

Bupropion1, the Molecule of the Week for May 2, 2011, is an antidepressant and antianxiety drug. Dextromethorphanis a commonly used cough suppressant. Now the two have been combined by Axsome Therapeutics (New York City) into a pill for treating major depressive disorder. Dextromethorphan is believed to modulate neurotransmission of glutamate, which likely plays a role in depression. In addition to its antidepressant properties, bupropion increases dextromethorphan levels in the blood.

1. CAS Reg. No. 34911-55-2.
2. CAS Reg. No. 125-71-3.

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