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Optically pure (+)-nicotine from (.+-.)-nicotine and biological comparisons with (-)-nicotine

Authors :
William L. Dewey
Louis S. Harris
C. Izazola-Conde
Ibrahim M. Uwaydah
May El
Thomas J. Bradshaw
W. C. Vincek
Billy R. Martin
Mario D. Aceto
Source :
Journal of Medicinal Chemistry. 22:174-177
Publication Year :
1979
Publisher :
American Chemical Society (ACS), 1979.

Abstract

Optically pure (+)-nicotine has been obtained from (+/-)-nicotine using a combination of d-tartaric acid and di-p-toluoyl-l-tartaric acid. As the di-d-tartrate salt, (+)-nicotine is less potent than (-)-nicotine di-l-tartrate in producing lethality in mice, on blood pressure in anesthetized rats, and in the isolated guinea-pig ileum, indicating substantial stereospecificity for nicotine receptors. Potency ratios are 0.14, 0.06, and 0.019, respectively.

Details

ISSN :
15204804 and 00222623
Volume :
22
Database :
OpenAIRE
Journal :
Journal of Medicinal Chemistry
Accession number :
edsair.doi.dedup.....26479c0d85f5598bbde72779e176a15a
Full Text :
https://doi.org/10.1021/jm00188a009