The chemistry of Anderson’s test for codeine
Department of Organic Chemistry, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), Mexico.
Research Article
International Journal of Scholarly Research in Chemistry and Pharmacy, 2023, 03(01), 001–004.
Article DOI: 10.56781/ijsrcp.2023.3.1.0025
Publication history:
Received on 09 July 2023; revised on 27 August 2023; accepted on 29 August 2023
Abstract:
The Anderson test for codeine entails the interaction of codeine with concentrated nitric acid and heating to dryness. These drastic conditions give rise to a long series of reactions that is provided for the first time. The initial steps are salt formation, codeine nitrate, followed by nitration of the aromatic ring at the activated position, C-2. Then occurs a molecular rearrangement analogue to the transformation of morphine to apomorphine. This implies a series of reactions that include dehydration of the allylic alcohol, double bond migration, 1,3-chain migration, cyclohexadiene formation, ring opening of the dihydro-furane ring followed by formation of a dihydro-phenanthrene structure. The last stage involves methylamine evolution after two C─N fissions and alkalinization of the reaction medium in order to obtain the free amine.
Keywords:
Allylic dehydration; Codeine nitrate; 1,3-migration; Molecular rearrangement; 2-Nitrocodeine; Phenanthrene derivatives
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Copyright © 2023 Author(s) retain the copyright of this article. This article is published under the terms of the Creative Commons Attribution Liscense 4.0