Detailed mechanistic investigation into the S-nitrosation of cysteamine

MK Morakinyo, I Chipinda, J Hettick…

Index: Morakinyo, Moshood K.; Chipinda, Itai; Hettick, Justin; Siegel, Paul D.; Abramson, Jonathan; Strongin, Robert; Martincigh, Bice S.; Simoyi, Reuben H. Canadian Journal of Chemistry, 2012 , vol. 90, # 9 p. 724 - 738

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Abstract

The nitrosation of cysteamine (H2NCH2CH2SH) to produce cysteamine-S-nitrosothiol (CANO) was studied in slightly acidic medium by using nitrous acid prepared in situ. The stoichiometry of the reaction was H2NCH2CH2SH+ HNO2→ H2NCH2CH2SNO+ H2O. On prolonged standing, the nitrosothiol decomposed quantitatively to yield the disulfide, cystamine: 2H2NCH2CH2SNO→ H2NCH2CH2S–SCH2CH2NH2+ 2NO. NO2 and N2O3 ...