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 Edit this at Wikidata
Chemical and physical data
FormulaC11H13ClN2
Molar mass208.69 g·mol−1
3D model (JSmol)
Density1.2 ± 0.1 g/cm3 g/cm3
  • 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 checkY
  • Key:NLPRAJRHRHZCQQ-IVZWLZJFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi and poison dart frogs from the Ameerega genus.[1] It was discovered by John W. Daly in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine occurs naturally 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.[2]

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.[3]

  1. ^ Fitch RW, Spande TF, Garraffo HM, Yeh HJ, Daly JW (March 2010). "Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi". Journal of Natural Products. 73 (3): 331–337. doi:10.1021/np900727e. PMC 2866194. PMID 20337496.
  2. ^ Garraffo HM, Spande TF, Williams M (April 2009). "Epibatidine: from frog alkaloid to analgesic clinical candidates: a testimonial to" true grit"!" (PDF). Heterocycles. 79 (1): 207–217. doi:10.3987/REV-08-SR(D)5.
  3. ^ Schwarcz J (2012). The Right Chemistry. Random House.