On the Interaction of Noscapine (Narcotine) with Ammonium Tellurate in Sulphuric Acid
Abstract
The purpose of this study is to clear up what is happening in the test tube during the interaction of ammonium tellurate with noscapine in sulphuric acid (Brociner test). The approach is a Theoretical Organic Chemistry Study based on the chemical deportment of reagent and substrate, the reaction medium, and experimental conditions. This point out that a redox process is going up, with the following results: meta-telluric acid is formed in situ whose protonation yields the reactive species. Reaction with the methylenedioxy group present in noscapine affords an oxonium salt. Reaction proceeds when a water molecule forms a hemiacetal and an organometallic ester, a tellurate. Acidolysis of the latter gives rise to a concerted mechanism involving five electron-shifts. This way the following compounds are formed: tellurious acid, an ortho-benzoquinone, and formaldehyde. Tellurium dioxide results by acid catalyzed dehydration of tellurious acid.
References
Demirkapu, M.J., & Yananli, H.R. (2020). Opium alkaloids. Retrieved from: https://www.intechopen.com/chapters/71219. https://doi.org/10.5772/intechopen.91326
Robiquet, P. (1831). Note sur la Narcotine, Journal de pharmacie et des sciences accessoires, 17(1), 637-643. https://gallica.bnf.fr>ark:>date>Journal+de+Pharmacie
Wisniak, J. (2013). Pierre-Jean Robiquet. Educación Química 24(51), 139-149. https://doi.org/10.1016/S0187-893X(13)72507-27>Pierre-Jean-Robiquet
Small, L.F., & Lutz, R.E. (1932). Chemistry of the Opium Alkaloids. Issue 103 of United States Public Health Service, pp. 42, 138. Washington, U.S. Government Printing Office. https://books.google.com.mx>chemistry-of-the-opium-alkaloids
Sánchez-Viesca, F., & Gómez, R. (2023). The chemistry of Husemann’s test for morphine. International Journal of Chemical and Pharmaceutical Research Updates, 01(01), 025-028. https://doi.org./10.53430/ijcpru.2023.1.1.0048
Sánchez-Viesca, F., & Gómez, R. (2023). Organometallic intermediates in Böttger test for glucose in urine. Magna Scientia Advanced Research and Reviews, 09(02), 051-054. https://doi.org/10.30574/msarr.2023.9.2.0147
Sánchez-Viesca, F., & Gómez, R. (2023). The chemistry of Anderson’s test for codeine. International Journal of Scholarly Research in Chemistry and Pharmacy, 03(01), 001-004. https://doi.org/10.56781/ijsrcp.2023.3.1.0025
Sánchez-Viesca, F., & Gómez, R. (2024). The chemistry of Hager’s test for brucine. Earthline Journal of Chemical Sciences, 11(1), 31-37. https://doi.org/10.34198/ejcs.11124.031037
Sánchez-Viesca, F., & Gómez, R. (2023). On the chemistry of Beckurt’s test for physostigmine: A novel hydride transfer. Magna Scientia Advanced Research and Reviews, 08(02), 022-025. https://doi.org/10.30574/msarr.2023.8.2.0098
Brociner, A. (1890). Le sulfotellurated’ammonium comme réactif d’alcaloides. Journal de pharmacie et de chimie, [5], 21, 468-469. https://gallica.bnf.fr>ark:date.r=Journal+de+pharmacie+et+de+chimie
Tellurium. Retrieved from: https://www.thermofisher.com>>tellurium
Tellurium. Retrieved from: https://byjus.com/chemistry/tellurium/
Tellurium element. Retrieved from: https://chemistrytalk.org/tellurium-element/
Telluric acid. Retrieved from; https://en.wikipedia.org/wiki/Telluric_acid
Telluric acid. From: https://www.chemspider.com/Chemical-Structure.55517.html
Ammonium tellurate. https://pubchem.ncbi.nlm.nih.gov>Ammonium+tellurate
Tellurium dioxide. https://en.wikipedia.org/wiki/Tellurium_dioxide
[ Teitel, S., O’Brien, J., & Brossi, A. (1972). Preferential cleavage of an aromatic methylenedioxy group in the presence of methoxyls with boron trichloride. Journal of Organic Chemistry, 37(21), 3368-3369. https://doi.org/10.1021/jo00986a046
Adaeva, O.I., Demchuk, D.V., & Semenor, V.V. (2023). 6,7-Dihydroxy-5,8-dimethoxy-2H-chromen-2-one. Molbank (3) M1702. https://doi.org/10.3390/M1702
Pesez, M., & Poirier, P. (1954). Méthodes et réactions de l’analyse organique, vol. III, p. 227. Paris, Masson.
This work is licensed under a Creative Commons Attribution 4.0 International License.
