STP802

    The Relationship Between the Toxicity and Structure of Nitroaromatic Chemicals

    Published: Jan 1983


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    Abstract

    The acute toxicities of nitrotoluene, dinitrotoluene, trinitrotoluene, aminonitrotoluene, aminodinitrotoluene, and dinitrobenzene isomers were evaluated in fathead minnows. For the nitroaromatics, toxicity appeared to be related to the number and orientation of nitro groups; compounds with nitro groups positioned ortho or para to each other were appreciably more toxic than isomers having the nitro groups in the meta orientation. In contrast, the toxicities of the aminonitrotoluenes and aminodinitrotoluenes were not related in any obvious way to their structures. Two mechanisms may account for the differences in toxicity between the nitroaromatic isomers: (1) nucleophilic displacement of a nitro group and (2) reduction of a nitro group. The available data indicate that reduction of a nitro group is the more likely pathway.

    Keywords:

    aquatic toxicology, structure-activity relationship, metabolic pathways, fathead minnows, nitroaromatics, nitrotoluene, dinitrotoluene, trinitrotoluene, aminonitrotoluene, aminodinitrotoluene, dinitrobenzene, trinitrobenzene, hazard assessment


    Author Information:

    Bailey, HC
    Director, Aquatic Toxicology Laboratory, and associate director, Pharmaceutical Analysis Department, SRI International, Menlo Park, CA

    Spanggord, RJ
    Director, Aquatic Toxicology Laboratory, and associate director, Pharmaceutical Analysis Department, SRI International, Menlo Park, CA


    Paper ID: STP33500S

    Committee/Subcommittee: E47.01

    DOI: 10.1520/STP33500S


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