(+)-epibatidine

Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadorian frog Epipedobates anthonyi and poison dart frogs from the genus Ameerega. 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 fro

Key facts

Drug.KEGG: C11690
Drug.C: 11
Drug.H: 13
Drug.Cl: 1
Drug.N: 2
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 443729000
Drug.IUPAC_name: (1R,2R,4S)-(+)-6-(6-Chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane
Drug.image: Epibatidine structure.svg
Drug.image_class: skin-invert-image
Drug.image2: Epibatidine molecule ball.png
Drug.CAS_number: 140111-52-0
Drug.UNII: M6K314F1XX
Drug.PubChem: 1204
Drug.DrugBank: DB07720
Drug.ChemSpiderID: 10399316
Drug.ChEBI: 4803

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Wikidata facts

Mass: 208.69

Show 6 more facts

chemical formula: C₁₁H₁₃ClN₂
isomeric SMILES: C1C[C@H]2[C@@H](C[C@@H]1N2)C3=CN=C(C=C3)Cl
canonical SMILES: C1CC2C(CC1N2)C3=CN=C(C=C3)Cl
Commons category: Epibatidine
density: 1.2
time of discovery or invention: 1974-00-00

Sources (4)

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Article

14 sections

Contents

History
Synthesis
Synthetic analogs
Chemical structure
Biological effects
Mechanism of action
Symptoms
Pharmacology
Potential medical uses
Alleged use as a poison
Antidote
See also
References
External links

Epibatidine is a neurotoxin that interferes with nicotinic and muscarinic acetylcholine receptors. These receptors are involved in the transmission of painful sensations, and in movement, among other functions. Epibatidine causes full body numbness, which can rapidly progress to full body 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.