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

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, an...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1979-02, Vol.22 (2), p.174-177
Main Authors: Aceto, Mario D, Martin, Billy R, Uwaydah, Ibrahim M, May, Everette L, Harris, Louis S, Izazola-Conde, Consuelo, Dewey, William L, Bradshaw, Thomas J, Vincek, W. C
Format: Article
Language:English
Subjects:
Animals
Blood Pressure - drug effects
Guinea Pigs
Heart Rate - drug effects
In Vitro Techniques
Lethal Dose 50
Male
Mice
Mice, Inbred ICR
Muscle Contraction - drug effects
Muscle, Smooth - drug effects
Nicotine - isolation & purification
Nicotine - pharmacology
Nicotine - toxicity
Rats
Stereoisomerism
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Summary: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.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00188a009