Occurrence of L-Nornicotine in Nicotiana sylvestris

Journal of Economic Entomology
1937.0

Abstract

The author studied the alkaloids of Nicotiana sylvestris plants grown by H. H. Smith under the direction of W. W. Garner. The alkaloids were found to be l-nornicotine (about 95% of the total alkaloids) and l-nicotine (about 5%), with the total alkaloidal content being approximately 1% in composite material from leaves and stems of plants used for seed production (some topped and suckered). Anabasine could not be detected. The alkaloids were extracted by successive boiling water extractions (with the final extraction via steaming), evaporation to a small volume, filtration, alkaline treatment, ether extraction, and distillation under reduced pressure. L-nornicotine was separated from l-nicotine by fractional distillation through a 30-cm. column. The identity of l-nicotine was confirmed by converting it to its picrate, which melted at 224°C (corr.) and showed no change in melting point when mixed with a known nicotine picrate. The identity of l-nornicotine was verified by preparing its picrate (melting at 191–192°C after recrystallization) and methylating it to produce nicotine, whose picrate matched the known sample. The absence of anabasine was confirmed by treating the alkaloids with sodium nitrite, which did not produce the insoluble nitroso derivative characteristic of anabasine.

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