Chlorination cimetidine

Chlorination of the antacid cimetidine leads to the formation of four major DBFs cimetidine sulfoxide, 4-hydroxyhnethyl-5-methyl-7//-imidazole, 4-chloro-5-methyl-7//-imidazole, and a product proposed to be either a jS- or (5-sulfam. The formation of the last three products resulted from unexpected reactions and more substantial structural changes than those t3q)ically observed in chlorination [93]. 

Buth JM, Arnold WA, McNeill K (2007) Unexpected products and reaction mechanisms of the aqueous chlorination of cimetidine. Environ Sci Technol 41(17) 6228-6233... 

Other work by Buth et al. (2007) examined formation, and subsequent removal of transformation products of cimetidine (an antacid). These degradates were shown to be more toxic overall than the parent compound, making them particularly problematic with respect to human health risk. The transformation products were also shown to be further degradable via chlorination to a degree highly dependent on chlorine dosage and pH. 

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