Synthesis and Structure of Some Phosphonylated Oximes Related to Organophosphate Nerve Agents

Boulet, Camille A.; Hansen, Arnold S.

doi:10.1080/10426509108038845

Cited by 14 publications

(1 citation statement)

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“…2-PAM or other oximes) must be administered before the aging process occurs. Because the toxicity of Novichok agents appears not to primarily rely on acetylcholinesterase inhibition, some have suggested that reactive oximes like potassium 2,3-butanedione monoximate (available in Europe only) are the preferred oximes for antidotal therapy [25,26].…”

mentioning

confidence: 99%

Novichok agents: a historical, current, and toxicological perspective

Chai

Hayes

Erickson

et al. 2018

Toxicology Communications

128

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The , or "newcomer" class of nerve agents are lesser characterized, weaponized organophosphate agents. The use of known agents in warfare is banned under the Chemical Weapons Convention of 1997. agents are considered more potent than VX gas and can be applied in unitary and binary forms. Like other nerve agents, agents irreversibly bind acetylcholinesterase and produce a cholinergic toxidrome. Uniquely, these agents are thought to also target neurons in the peripheral nervous system. Delayed treatment or massive exposure may therefore cause a debilitating neuropathy. The recent 2018 assassination attempt of Russian dissident Sergei Skripal and his daughter Yulia in the United Kingdom highlights the importance of recognizing the potential lethal effects of these nerve agents. Treatment of agent poisoning is similar to management of other nerve agents. Given increasing worldwide incidents attributed to chemical weapons such as agents, clinicians should know how to rapidly recognize symptoms of acute poisoning and administer life-saving antidotal therapy, when indicated.

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confidence: 99%

Novichok agents: a historical, current, and toxicological perspective

Chai

Hayes

Erickson

et al. 2018

Toxicology Communications

128

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The Chemistry of Organophosphorus Chemical Warfare Agents

Black

Harrison

2009

Patai's Chemistry of Functional Groups

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Introduction Historical Development Synthesis Chemical and Physical Properties Decontamination Spectroscopic Analysis Chromatographic Analysis Trace Analysis of Nerve Agents and their Degradation Products in Verification Generic Detection of Nerve Agents Mechanism of Action Toxicodynamics Therapy and Pretreatment Structure—Toxicity Relationships Control Under the Chemical Weapons Convention

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Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Palácios

Santos

Vicario

et al. 2010

Patai's Chemistry of Functional Groups

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This comprehensive chapter, organized in three different sections, includes new topics focused on preparation and synthetic applications of phosphorus functionalized hydroxylamines, oximes and hydroxamic acids. The first section comprises the synthesis of phosphorus O ‐substituted hydroxylamines either through phosphorus‐oxygen or nitrogen‐oxygen single bond formation. The synthesis of N ‐substituted hydroxylamines is also covered in this first section by means of phosphorus‐nitrogen or carbon‐nitrogen bond formation reactions. This section also includes several transformations of phosphorus substituted hydroxylamines including among others: rearrangement, hydrolysis, reduction and oxidation reactions. Functionalized oximes containing phosphorus substituents including O ‐ and C ‐substituted oximes, and oximes with α‐ and β‐phosphorated moieties are covered in a second section. This provides an introduction to the common approaches to synthesize phosphorus substituted oximes, and the application of phosphorated oximes to the preparation of more elaborated compounds have been described. Some of the synthetic applications methods covered in the second section are fragmentation and rearrangement reactions, nucleophilic substitution at the phosphorus atom, intramolecular reactions, radical reactions, reduction of carbon‐nitrogen double bond, oxidation reactions, olefination reactions, dehydratation of oximes. The third section is dedicated to the synthesis and reactivity of phosphorus O ‐, N ‐, and C ‐substituted hydroxamic acid derivatives, spanning the few reports in the literature covering this topic. An extensive and current list of references and a subject index complete the chapter. Phosphorus Substituted Hydroxylamine Derivatives Phosphorus Substituted Oximes Phosphorus Substituted Hydroxamic Acid Derivatives Acknowledgments

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Synthesis and Structure of Some Phosphonylated Oximes Related to Organophosphate Nerve Agents

Cited by 14 publications

References 14 publications

Novichok agents: a historical, current, and toxicological perspective

Novichok agents: a historical, current, and toxicological perspective

The Chemistry of Organophosphorus Chemical Warfare Agents

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

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