Dextromethorphan is an optically-active dextrorotary enantiomer of the codeine analog of levorphanol. It shows high affinity binding to several regions of the brain, including the medullary cough center. Dextromethorphan is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity.[1] The chemical formula of Dextromethorphan is C18H25NO and its IUPAC name is (+)-3-methoxy-17-methyl-9α,13α,14α-morphinan. As the pure free base, dextromethorphan occurs as an odorless, white to slightly yellow crystalline powder. Its solubility in water is 74.7 mg/L. Dextromethorphan is commonly available as the monohydrated hydrobromide salt but can be converted to other forms such as Dextromethorphan Citrate. Dextromethorphan Hydrobromide is soluble in water 15 g/L at 25° C, 100g/L in ethanol, practically insoluble in ether and freely soluble in chloroform.[2]

dextromethorphan molecule

· Uncompetitive N-methyl-D-aspartate (NMDA) receptor antagonist
· σ1 and σ2 sigma receptor agonist
· α3β4, α4β2, and α7 nicotinic acetylcholine receptor antagonist
· Serotonin reuptake inhibitor
· Norepinephrine reuptake inhibitor
· μ-Opioid receptor agonist (very weak)
· NADPH oxidase inhibitor

Dextromethorphan is rapidly absorbed from the gastrointestinal tract and metabolized in the liver by the cytochrome P450 enzymes 2D6 and 3A4. Its metabolites are Dextrorphan, 3-Methoxymorphinan and 3-Hydroxymorphinan. The half-life of Dextromethorphan is 3-6 hours.

Main article: Synthesis of Morphinans

^ "Dextromethorphan (DB00514)" Drugbank. 2009-04-16 16:47:46. 23 April 2010.http://www.drugbank.ca/drugs/DB00514
^ "Dextromethorphan" Inchem. 25 April 2010.http://www.inchem.org/documents/pims/pharm/pim179.htm

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