Chlorination acetaminophen

Examples of the application of HPLC to the analysis of (a) acetaminophen, salicylic acid, and caffeine (b) chlorinated pesticides (c) tricyclic antidepressants and (d) peptides. (Chromatograms courtesy of Alltech Associates, Inc. Deerfield, IL). 

Transformation of the widely used over-the-counter analgesic acetaminophen (paracetamol) during chlorination produced the toxic 1,4-benzoquinone via the A-acetylquinone-imine and minor amounts of products from chlorination of the phenolic ring (Bedner and Maccrehan 2006). 

Bedner M, WA Maccrehan (2006) Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and iV-acetyl-/)-benzoquinone imine. Environ Sci Technol 40 516-522. 

The reaction of the lipid-regulator gemfibrozil with free chlorine yielded four chlorinated derivatives of this compound [94]. Chlorination of acetaminophen (paracetamol) generated 11 discernible DBFs, including the toxic compounds 1,4-benzoquinone and A-acetyl-p-benzoquinone imine and two ring chlorination products, chloro-4-acetamidophenol and dichloro -acetamidophenol [95]. 

No information was located regarding toxic interactions of 1,1-dichloroethane with other xenobiotics. Evidence exists to indicate that 1,1- dichloroethane is detoxified by glutathione (Colacci et al. 1985). Thus, it is likely that other substances that deplete glutathione stores such as other chlorinated hydrocarbons (e.g. 1,1-dichloroethane and 1,2-dichloroethane), acetaminophen, and bromobenzene may enhance the toxicity of 1,1- dichloroethane. Substances that alter the activity of the microsomal enzymes that are responsible for the metabolism of 1,1 -dichloroethane may also affect the toxicity of this chemical. For example, it has been shown that ethanol increases the metabolism of 1,1 -dichloroethane in vitro (Sato et al. 1980). 

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