Epibatidine

Epibatidine has three chiral centers

Epipedobates tricolor

 

 

Usually we think of natural products as compounds that come from plants. However epibatidine is a 

compound that is actually produced by an animal. This compound  is the poison that made the poison dart frog so famous. Historically, this frog, Epipedobates tricolor was the frog that many tribes in the Colombian rainforest used to coat their darts in, giving it its name. The poison secreted form the frogs back  is potent enough that a small amount of it could kill something as large as a water buffalo.

The poison form the poison dart frog was first analyzed by Dr. John Daly in 1992. He found that there were a large amount of painkillers actually present in the poison of the frog. Testing was begun on mice, where they received a small dose of the poison and were tested for how long it took them to take their paw off of a hot plate, or produce a response such as paw licking. The poisonous secretion was found to be so powerful that only 5 micrograms acted as an effective painkiller in the mice. This is a huge difference in comparison with the 10 milligrams of morphine that had to be administered to the mice to elicit the same response. However the amount of poison extracted from the frog was too small for extensive testing and the frog itself was becoming endangered, which stopped the study. It wasn’t until years later that synthetic methods were discover to produce larger amounts of this toxin for further research.

Nicotine vs Epibatidine

The poison form this frog actually proved to be, similar in structure to nicotine. It actually has the ability to bind to nicotinic acetylcholine receptors, which produce the painkiller or analgesic type of response similar to that of morphine and ibuprofen. However, the actual pain reliving compound found in the frog poison proved to have too many adverse side effects to be used as an actual remedy for pain. The compound is now a model for scientists to produce a painkiller that is just as effective but without the toxic side effects.

Sources:

 http://chlorine.americanchemistry.com/Science-Center/Chlorine-Compound-of-the-Month-Library/Epibatidine-Natural-Frog-Poison-with-a-Surprising-Benefit-to-Humans

http://bja.oxfordjournals.org/content/81/1/69.full.pdf

http://pubchem.ncbi.nlm.nih.gov/compound/Epibatidine#section=Computed-Properties

http://img.photobucket.com/albums/v395/elmoisfive/Nicotine_EpibatidineComparison2.jpg

data:image/jpeg;base64,/9j/4AAQSkZJRg