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Epibatidine Properties

Epibatidine

Molecule Structure Image

Description

 

Epibatidine is an alkaloid found on the skin of the endangered Ecuadorian frog, Epipedobates tricolor. These frogs, like other poison dart frogs, are best known for their ability to sequester poisons from their prey and secrete these poisons onto their backs. The one toxin that distinguishes the Epipedobates tricolor from other frogs in his family is epibatidine. The frog uses the compound to protect itself from predators. Animals many times larger would die from the small amounts of epibatidine that the frog secretes. Epibatidine, which was being researched in 1974, turned out to be a very powerful analgesic. This had proven a powerful argument for further research, which has shown that epibatidine has gastrointestinal side effects. This gives the compound a very small therapeutic index and it is very unlikely to ever appear on the medicinal market.

Chemical Properties

CAS Number 140111-52-0
ChEBI 691080
Density 1.223g/cm3
IUPAC Name (1R,2R,4S)-(+)-6-(6-Chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane
InChI 1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2/t8-,9-,10+/m1/s1
InChIKey NLPRAJRHRHZCQQ-BBBLOLIVSA-N
Molar Mass 208.69 g/mol
Molecular Formula C11H13ClN2
Synonyms 7-Azabicyclo[2.2.1]heptane,2-(6-chloro-3-pyridinyl)-, (1R,2R,4S)-;(+)-Epibatidine;(1R-exo)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane;Epibatidine