None Francisco Sánchez Viesca, None Reina Gómez Gómez
{"title":"The chemistry of Anderson’s test for codeine","authors":"None Francisco Sánchez Viesca, None Reina Gómez Gómez","doi":"10.56781/ijsrcp.2023.3.1.0025","DOIUrl":null,"url":null,"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.","PeriodicalId":479524,"journal":{"name":"International Journal of Scholarly Research in Chemistry and Pharmacy","volume":"10 1","pages":"0"},"PeriodicalIF":0.0000,"publicationDate":"2023-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"International Journal of Scholarly Research in Chemistry and Pharmacy","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.56781/ijsrcp.2023.3.1.0025","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1
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.