Jumping rats | FROGS TO FAGS

From frogs to fags

A history of Epibatidine continued


On the development of NMR in 1986, research on epibatidine deduced the structure and many methods of synthesis were formulated, some of which are described here.

  The structure of epibatidine itself suggested a mechanism for the analgesic activity. The similarity of nicotine and epibatidine was observed. Nicotine had long been known to have a mild painkilling effect, but responses of smokers were so varied the exact mechanism had not been studied. It was known that nicotinic receptors existed, so hyptheses were drawn up suggesting nicotinic receptors as a mode of action for epibatidine.


 There was found to be 2 optical isomers of epibatidine, and only the (+)-Epibatidine was secreted by the frogs, whereas on testing, both enantiomers were discovered to be effective as painkillers, so the synthesis of a racemate would not affect activity.

Hundreds and hundreds of molecules structurally similar to epibatidine started to be tested for analgesic activity without the side effects of epibatidine. The article published by Daly in the prestigious journal, Journal of the American Chemical Society in 1992 highlighted these discoveries.
One of the newest developments, in 1997, turned up the molecule ABT-594 which has been shown to be a powerful analgesic, with very low toxicity.

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