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

J Med Chem. 1979 Feb;22(2):174-7. doi: 10.1021/jm00188a009.

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.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 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

Substances

  • Nicotine