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. 2021 Jun 14;11:12487. doi: 10.1038/s41598-021-91792-1

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© The Author(s) 2021

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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Proposed chemistry of NDMA formation from DMF during sartan production. The active pharmaceutical ingredient in sartan drugs has a tetrazole ring and the conventional method to produce this ring was reported to be slow. In order to accelerate the production process, a synthesis procedure that uses the solvent, dimethylformamide (DMF) and sodium azide (in place of tributyltin azide) was introduced in 2012. During tetrazole synthesis, a small amount of dimethylamine would be formed from DMF. The synthetic process also involves the use of nitrous acid to dispose of the excess sodium azide. This nitrous acid (a nitrosating agent) which is produced from sodium nitrite under acidic conditions can react with dimethylamine to form NDMA. (R = aryl, alkyl or vinyl; DMF = dimethylformamide; NDMA = N-nitrosodimethylamine). Figure adapted from^2,53–55.