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Synthesis

Deuterated Drugs Redux

October 12, 2009 | A version of this story appeared in Volume 87, Issue 41

The article on deuterated drugs prompts me to resurrect for your readers an obscure but important result using the deuterium isotope effect to overcome insect resistance to DDT. In 1963, M. K. K. Pillai and A. W. A. Brown reported that DDT, deuterated at C-2, was very effective against mosquito species that were resistant to 2-H-DDT. In fact, 2-D-DDT was a very potent insecticide, and the paper describes the inability of mosquito species to develop resistance.

This experiment was based on the concept, put forward by the late D. J. Hennessy of Fordham University, that resistant species had developed a dehydrochlorinase that converted DDT to nontoxic DDE, whereas the deuterium isotope effect would slow down the process enough for the active insecticide to have its desired effect. Hennessy published a synthesis paper (J. Agric. Food Chem. 1963, 11, 47), while Pillai and Brown published their data in the Proceedings of the New Jersey Mosquito Extermination Association (1963, page 235). This work took place during the Rachel Carson/"Silent Spring" era when the idea that DDT was a bad thing took over. So, this "proof of concept" never led to a large-scale practical application.

Richard W. Franck
New York City

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