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F.","year":"1991","journal-title":"Drug Metab. Rev."},{"key":"tx0002280b00011\/tx0002280b00011_1","volume-title":"Pulmonary toxicity of trichloroethylene in mice:\u2009 covalent binding and morphological manifestations. Drug Metab. Dispos. 17, 106\u2212113","author":"Forkert P. G.","year":"1989"},{"key":"tx0002280b00012\/tx0002280b00012_1","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1021\/tx00043a001","volume":"8","author":"Goeptar A. R.","year":"1995","journal-title":"Chem. Res. Toxicol."},{"key":"tx0002280b00013\/tx0002280b00013_1","doi-asserted-by":"crossref","DOI":"10.1080\/10408440091159202","volume":"30","author":"Br\u00fcning T.","year":"2000","journal-title":"Crit. Rev. Toxicol."},{"key":"tx0002280b00014\/tx0002280b00014_1","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1289\/ehp.772191","volume":"21","author":"Leibman K. C.","year":"1977","journal-title":"Environ. 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