On the mechanism of Siebold’s test for morphine Article Swipe

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Francisco Sánchez‐Viesca , Reina Gómez ·

YOU? · · 2024 · Open Access · · DOI: https://doi.org/10.53430/ijcpru.2024.2.1.0021

In this communication the reaction course of Siebold’s test for morphine is provided. The test is based on the interaction of the alkaloid in sulphuric acid with potassium perchlorate. Perchloric acid is the intermediate that gives rise the reactive species, ClO3+. A mixed perchlorate is formed by interaction with the phenolic group at C-3 in morphine. Protonation of this ester induces nucleophilic reaction at C-2 (Umpolung). A new perchlorate results with concomitant ketone formation at C-3 and elimination of chloric acid (first redox reaction). Enolization restores ring aromatization, and protonation of the perchlorate at C-2 produces a concerted push-pull mechanism, via three electron-shifts, that gives rise separation of chloric acid and formation of an ortho-quinone (second redox reaction).

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Morphine Mechanism (biology) Test (biology) Pharmacology Medicine Geology Philosophy Epistemology Paleontology

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Type: article
Language: en
Landing Page: https://doi.org/10.53430/ijcpru.2024.2.1.0021
OA Status: hybrid
Cited By: 3
Related Works: 10
OpenAlex ID: https://openalex.org/W4406406140

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OpenAlex ID: https://openalex.org/W4406406140

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DOI: https://doi.org/10.53430/ijcpru.2024.2.1.0021

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Title: On the mechanism of Siebold’s test for morphine

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Type: article

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Language: en

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Publication year: 2024

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Publication date: 2024-03-30

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Authors: Francisco Sánchez‐Viesca, Reina Gómez

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Landing page: https://doi.org/10.53430/ijcpru.2024.2.1.0021

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Open access: Yes

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OA status: hybrid

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OA URL: https://doi.org/10.53430/ijcpru.2024.2.1.0021

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Concepts: Morphine, Mechanism (biology), Test (biology), Pharmacology, Medicine, Geology, Philosophy, Epistemology, Paleontology

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Cited by: 3

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Citations by year (recent): 2024: 3

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Related works (count): 10

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