The Chemistry of van de Moer Test for Cytisine

  • Francisco Sánchez-Viesca Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), Mexico
  • Reina Gómez Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), Mexico
Keywords: cytisine, free radical chemistry, 2-pyridinone, quinolizidine, reactive intermediates, rearrangement, smoking cessation

Abstract

Cytisine is an alkaloid with biological activity that is used as medication for smoking cessation treatment. It is a quinolizidine derivative, one ring being 2-pyridinone, and there is a third cycle, a disubstituted piperidine. Thus, the analytical chemistry of this compound is relevant. In this communication we provide the chemistry involved in the spot test for cytisine identification by means of ferric chloride/hydrogen peroxide. The electron flow, step by step, is given from the alkaloid to the final colored products. The sequence is based on the chemical properties of the substrate and reagents, disclosing the series of reactions occurring in this assay. The process is in accordance with the experimental results. We also give the mechanism of cytisine degradation, from a quinolizidine system to 6,8-dimethyl quinoline, which involves an interesting rearrangement.

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Published
2021-04-21
How to Cite
Sánchez-Viesca, F., & Gómez, R. (2021). The Chemistry of van de Moer Test for Cytisine. Earthline Journal of Chemical Sciences, 6(1), 15-22. https://doi.org/10.34198/ejcs.6121.1522
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Articles