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Re: Genotoxic TCAs

Posted by desolationrower on March 12, 2009, at 14:06:51

In reply to Re: Genotoxic TCAs NickCave, posted by Phillipa on March 12, 2009, at 13:45:47

Van Schaik and Graf (1991, 1993) evaluated TCAs using a genotoxicity assay involving wing development in Drosophila melanogaster aimed at identifying potential carcinogens. They found that amitriptyline, maprotiline, nortriptyline, and protriptyline were not genotoxic, whereas clomipramine, desipramine, and imipramine clearly were. Since the former four compounds have a carbon atom at position five in the six- or seven-membered central ring, and the latter three have a nitrogen at that position in the seven-membered central ring, they hypothesized that the nitrogen atom in the seven-membered central ring was responsible for the genotoxicity. Recently, Graf (personal communication) evaluated the genotoxicity of amoxapine, doxepin, and trimipramine using the same assay. As expected on the basis of the structural hypothesis, trimipramine was genotoxic. Although doxepin has a carbon at position five, its structure is atypical in that an oxygen atom occupies position eleven in the central ring (Budavari et al, 1989); it was also genotoxic. Several aspects of the structure of amoxapine are atypical (Budavari et al, 1989); the central ring includes both a nitrogen and an oxygen atom it too was genotoxic.
The effects of tricyclic antidepressants on breast cancer risk
C R Sharpe1,2, J-P Collet1,3, E Belzile1, J A Hanley3 and J-F Boivin1,3 2001





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