The 7-aza-norbornane nucleus of epibatidine: 7-aza-bicyclo-[2.2.1]heptan-7-ium chloride.

ABSTRACT: 7-Aza-bicyclo-[2.2.1]heptane (7-aza-norbornane) is a bridged heterocyclic nucleus found in epibatidine, the alkaloid isolated from the skin of the tropical poison frog Epipedobates tricolor. Since epibatidine is known as one of the most potent acetyl-choline nicotinic receptor agonists, a plethora of literature has been devoted to this alkaloid. However, there are no structural data on the unsubstituted 7-aza-norbornane, the parent bicyclic ring of epibatidine and its derivatives. We herein present the structural characterization of the 7-aza-bicyclo-[2.2.1]heptane parent ring as its hydro-chloride salt, namely 7-aza-bicyclo-[2.2.1]heptan-7-ium chloride, C₆H₁₂N⁺·Cl^-. The compete cation is generated by a crystallographic mirror plane with the N atom lying on the mirror, as does the chloride anion. In the crystal, the cations are linked to the anions by N-H?Cl hydrogen bonds, which generate [001] chains.

SUBMITTER: Britvin SN 

PROVIDER: S-EPMC5588587 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature