Epibatidine

Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi and poison dart frogs from the Ameerega genus. It was discovered by John W. Daly in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine is the first observed example of a chlorinated alkaloid remains controversial, due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples from other batches of the same species of frog failed to yield epibatidine.

Not to be confused with Eptifibatide.
Epibatidine
Identifiers
  • (1R,2R,4S)-(+)-6-(6-Chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard100.162.281
Chemical and physical data
FormulaC11H13ClN2
Molar mass208.69 g·mol−1
3D model (JSmol)
Density1.2 ± 0.1 g/cm3
SMILES
  • ClC1=CC=C([C@@H]2C[C@]3([H])CC[C@@]2([H])N3)C=N1
  • 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+/m0/s1 Y
  • Key:NLPRAJRHRHZCQQ-IVZWLZJFSA-N Y
 NY (what is this?)  (verify)

Epibatidine is toxic. Its toxicity stems from its ability to interact with nicotinic and muscarinic acetylcholine receptors. These receptors are involved in the transmission of painful sensations, and in movement, among other functions. Epibatidine then causes numbness, and, eventually, paralysis. Doses are lethal when the paralysis causes respiratory arrest. Originally, it was thought that epibatidine could be useful as a drug. However, because of its unacceptable therapeutic index, it is no longer being researched for potential therapeutic uses.

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