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Synthesis of optically pure epibatidine analogs: (1R, 2R, 5S)-2β-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane and (1R, 2S, 5S)-2α-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane from (−)-cocaine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
38
Issue
32
Identifiers
DOI: 10.1016/s0040-4039(97)01276-8

Abstract

Abstract Two optically pure epibatidine analogs, 4 and 5, which contain the 8-azabicyclo[3.2.1]octane ring system were synthesized from (−)-cocaine. The nicotinic receptor binding affinity and the stimulant activity of 4 and 5 were measured to be significantly lower than racemic epibatidine (± -1).

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