Molecule of the Week
January 13, 2014
Cystamine is a poisonous, viscous oil that is formed when the amino acid cystine is thermally decarboxylated. C. Neuberg et al. discovered this reaction in 1907 when they attempted to distill cystine. In 1940, in the course of synthesizing vitamin B1-like drugs, E. J. Mills, Jr., and M. T. Bogert synthesized cystamine by oxidizing cysteamine (2-mercaptoethylamine) with H2O2.
Cystamine itself is unstable and cannot be distilled without decomposing. It is usually handled as the dihydrochloride salt. Its uses include derivatizing polymers for analysis by liquid chromatography, cross-linking polymers to make hydrogels, and functionalizing nanoparticles that are used for siRNA and DNA delivery.