maleic-acid and Common-Cold

Different pharmaceutical preparations against the common cold contain acetaminophen, phenylephrine hydrochloride, and chlorpheniramine maleate. A degradation product had been discovered in these preparations after short- and long-term stability studies. This degradation product was isolated and found to be an adduct of phenylephrine and maleic acid. An account of the isolation and characterization of this compound was published. Our interest in this area led us to synthesize the compound, and we found that the synthesized compound does not have the same spectroscopic properties described in the original paper. Our subsequent work identified the structure of the degradation product as a "Michael addition" product of phenylephrine and maleic acid.

Topics: Acetaminophen; Analgesics, Non-Narcotic; Anti-Allergic Agents; Chemistry, Pharmaceutical; Chlorpheniramine; Common Cold; Drug Stability; Magnetic Resonance Spectroscopy; Maleates; Nasal Decongestants; Phenylephrine