3610. Epibatidine

Nomenclature

CAS number: 140111-52-0
(1R,2R,4S)-2-(6-Chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane.
C11H13ClN2; mol wt 208.69.
C 63.31%, H 6.28%, Cl 16.99%, N 13.42%.

Description and references

First naturally occurring non-opioid, organochlorine, alkaloid analgesic; isolated from skin of the Ecuadoran poison frog, Epipedobates tricolor. Isoln and structural determn: T. F. Spande et al., J. Am. Chem. Soc. 114, 3475 (1992). First natural product identified which contains the 7-azabicyclo[2.2.1]heptane ring system. Synthesis of (±)-form: C. A. Broka, Tetrahedron Lett. 1993, 3251.

Chemical structure

Properties

Basic, relatively polar, colorless oil. uv max (methanol): 217 nm, shoulder 250-280 nm.