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Synthesis of four racemic nicotine isotopomers doubly labelled with stable isotope

✍ Scribed by Wilfried Hatton; Virginie Silvestre; Richard J. Robins; Monique Mathé-Allainmat; Jacques Lebreton

Publisher
John Wiley and Sons
Year
2009
Tongue
French
Weight
167 KB
Volume
52
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Four racemic nicotine isotopomers, doubly labelled with stable isotope, were prepared for use in studies of plant metabolism. First, starting from halogeno nicotinates, one deuterium was introduced into the pyridine moiety by reductive dehalogenation with zinc, and choosing deuterated acetic acid as the acidic medium. Pyridine ^2^H‐labelled nornicotine derivatives were then formed in two reaction steps, a condensation reaction with N‐vinylpyrrolidinone followed by catalytic hydrogenation. The deuteromethylation of these monodeuterated nornicotines was achieved by reduction of the corresponding ethyl carbamates with deuterated lithium aluminium hydride. The four regioisotopomers obtained were at the least 90% labelled on each site, sufficient for the metabolic studies envisaged. Copyright © 2009 John Wiley & Sons, Ltd.

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