Rev Environ Contam Toxicol 173:39–83 © Springer-Verlag 2002 39 Toxicity of Azaarenes Eric A.J. Bleeker, Saskia Wiegman, Pim de Voogt, Michiel Kraak, Heather A. Leslie, Elske de Haas, and Wim Admiraal Contents I. Introduction ................................................................................................... 40 II. Biotransformation and Metabolism ............................................................... 41 A. Introduction .............................................................................................. 41 B. Quinoline and Isoquinoline ....................................................................... 42 C. Benzoquinolines ........................................................................................ 44 D. Azaarenes with More Than Three Condensed Aromatic Rings ................ 46 E. Metabolites Occurring in the Environment ............................................... 47 III. Direct Toxicity .............................................................................................. 48 A. Introduction .............................................................................................. 48 B. Toxicity of Quinoline and Acridine .......................................................... 49 C. Toxicity of Ranges of Azaarenes .............................................................. 50 D. Biotransformation and Toxicity ................................................................ 52 E. Chronic Toxicity ....................................................................................... 52 IV. Photochemical Transformation and Phototoxic Effects of Azaarenes ........... 53 A. Introduction .............................................................................................. 53 B. Mechanisms and Kinetics of Photochemical Reactions of (N)PAHs ........ 53 C. Phototoxic Effects of (N)PAHs and Their Photoproducts on Aquatic Organisms ............................................................................... 57 V. Genotoxicity and Carcinogenicity ................................................................. 62 A. Introduction .............................................................................................. 62 B. Quinoline and Isoquinoline ....................................................................... 63 C. Benzoquinolines ........................................................................................ 63 D. Benzacridines ............................................................................................ 65 E. Dibenzacridines ......................................................................................... 66 VI. Teratogenicity and Other Developmental Effects .......................................... 66 VII. Comparing Azaarenes and Homocyclic PAHs .............................................. 67 A. Comparing Toxicity .................................................................................. 67 B. Risk Assessment ....................................................................................... 69 VIII. Conclusions ................................................................................................... 69 Summary ................................................................................................................ 70 References .............................................................................................................. 72 _______________ Communicating editor: Pim de Voogt. E.A.J. Bleeker ()·S. Wiegman·M. Kraak·H.A. Leslie·E. de Haas·W. Admiraal Department of Aquatic Ecology and Ecotoxicology, IBED, University of Amsterdam, Kruislaan 320, 1098 SM Amsterdam, The Netherlands. P. de Voogt Department of Environmental and Toxicological Chemistry, IBED, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.