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 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.[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]
^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.
^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 (inactive 2024-03-07).{{cite journal}}: CS1 maint: DOI inactive as of March 2024 (link)
^Schwarcz J (2012). The Right Chemistry. Random House.
Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi and poison dart frogs from the Ameerega genus. It was...
lipophilic alkaloid toxins such as allopumiliotoxin 267A, batrachotoxin, epibatidine, histrionicotoxin, and pumiliotoxin 251D through their skin. Alkaloids...
renin-binding protein. The penultimate step in Zhang & Trudell's classic epibatidine synthesis is an example of epimerization. Pharmaceutical examples include...
definition), acetylcholine (the endogenous agonist of nAChRs), choline, epibatidine, lobeline, varenicline and cytisine. Nicotine has been known for centuries...
decomposition, forest fires, and volcanoes. The natural organochloride epibatidine, an alkaloid isolated from tree frogs, has potent analgesic effects and...
developed as a less toxic analogue of the potent frog-derived alkaloid epibatidine, which is around 200 times stronger than morphine as an analgesic but...
endogenous agonist acetylcholine, agonists of the nAChR include nicotine, epibatidine, and choline. Nicotinic antagonists that block the receptor include mecamylamine...
epibatidine, which is about 200 times stronger than morphine as an analgesic, but produces extremely dangerous toxic side effects. Like epibatidine,...
males carry the tadpoles to sites with running water. The frogs secrete epibatidine, a chemical of pharmacological interest. Phantasmal poison frogs live...
Global Information
(what is this?) (verify)