Dicyclohexyl Phosphorofluoridate
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Dicyclohexyl Phosphorofluoridate
Dicyclohexyl phosphorofluoridate (DCFP), also known as TL-941 or T-1840, is an extremely toxic organophosphorus compound with powerful anticholinesterase action. It's a colorless liquid that is extremely resistant to hydrolysis. DCFP can be produced by reaction of cyclohexanol with phosphoryl dichloride fluoride Phosphoryl dichloride flouride is an inorganic compound with the chemical formula . Synthesis It is made by reacting phosphorus pentachloride with potassium monofluorophosphate: : Reactions The reaction with two equivalents of cyclohexanol yi .... See also * Diisopropyl phosphorofluoridate (DFP) References {{Acetylcholine metabolism and transport modulators Acetylcholinesterase inhibitors Phosphorofluoridates Cyclohexyl compounds ...
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Biochemical Journal
The ''Biochemical Journal'' is a peer-reviewed scientific journal which covers all aspects of biochemistry, as well as cell and molecular biology. It is published by Portland Press and was established in 1906. History The journal was established in 1906 by Benjamin Moore, holder of the first UK chair of biochemistry at the University of Liverpool, with financial support from Edward Whitley, an heir of the Greenall Whitley brewers.Clark J. Biochemical Journal Centenary (2006)
(accessed 30 September 2007)
The two served as the first editors and the journal was initially published by the
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Organophosphorus Compound
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX (nerve agent), VX nerve agents. Phosphorus, like nitrogen, is in pnictogen, group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties. The definition of organophosphorus compounds is variable, which can lead to confusion. In industrial and environmental chemistry, an organophosphorus compound need contain only an organic substituent, but need not have a direct phosphorus-carbon (P-C) bond. Thus a large proportion of pesticides (e.g., malathion), are often included in this class of compounds. Phosphorus can adopt a v ...
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Anticholinesterase
Cholinesterase inhibitors (ChEIs), also known as anti-cholinesterase, are chemicals that prevent the breakdown of the neurotransmitter acetylcholine or butyrylcholine by cholinesterase. This increases the amount of the acetylcholine or butyrylcholine in the synaptic cleft that can bind to muscarinic receptors, nicotinic receptors and others. This group of inhibitors is divided into two subgroups, acetylcholinesterase inhibitors (AChEIs) and butyrylcholinesterase inhibitors (BChEIs). ChEIs may be used as drugs for Alzheimer's and myasthenia gravis, and also as chemical weapons and insecticides. Side effects when used as drugs may include loss of appetite, nausea, vomiting, loose stools, vivid dreams at night, dehydration, rash, bradycardia, peptic ulcer disease, seizures, weight loss, rhinorrhea, salivation, muscle cramps, and fasciculations. ChEIs are indirect-acting parasympathomimetic drugs. ChEls are widely used as chemical weapons. Since November 2019 the group of ACheI ...
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Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of Biomolecule, biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the su ...
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Cyclohexanol
Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Production Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: :2 C6H12 + O2 → 2 C6H11OH This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol: :C6H5OH + 3 H2 → C6H11OH This process can al ...
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Phosphoryl Dichloride Fluoride
Phosphoryl dichloride flouride is an inorganic compound with the chemical formula . Synthesis It is made by reacting phosphorus pentachloride with potassium monofluorophosphate: : Reactions The reaction with two equivalents of cyclohexanol yields the nerve agent dicyclohexyl phosphorofluoridate. The same reaction with isopropanol instead of cyclohexanol yields the nerve agent diisopropyl fluorophosphate. Two equivalents of sodium azide can replace the chlorine atoms with azide groups. Silver cyanate can replace them with cyanate groups. Hexamethyldisiloxane can replace one of the two chlorine atoms with a trimethylsilyl ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R†.... References Phosphorus oxohalides Nerve agent precursors {{inorganic-compound-stub ...
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Diisopropyl Fluorophosphate
Diisopropyl fluorophosphate (DFP) or Isoflurophate is an oily, colorless liquid with the chemical formula C6H14FO3P. It is used in medicine and as an organophosphorus insecticide. It is stable, but undergoes hydrolysis when subjected to moisture. Uses in medicine Diisopropyl fluorophosphate is a parasympathomimetic drug irreversible anti-cholinesterase and has been used in ophthalmology as a miotic agent in treatment of chronic glaucoma, as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of its acetylcholinesterase inhibitory properties and ability to induce delayed peripheral neuropathy. Uses as toxin The marked toxicity of esters of monofluorophosphoric acid was discovered in 1932, when Willy Lange and his PhD student Gerda von Krueger prepared the methyl, ethyl, n-propyl, and n-butyl esters and incidentally experienced their toxic effects. Another homologue of this series of esters, Diisopropyl fluorophosphate, was developed by B ...
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Acetylcholinesterase Inhibitors
Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from Hydrolysis, breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level and duration of action of acetylcholine in the central nervous system, Autonomic ganglion, autonomic ganglia and neuromuscular junctions, which are rich in acetylcholine receptors. Acetylcholinesterase inhibitors are one of two types of cholinesterase inhibitors; the other being Butyrylcholinesterase#Inhibitors, butyryl-cholinesterase inhibitors. Acetylcholinesterase is the primary member of the cholinesterase, cholinesterase enzyme family. Acetylcholinesterase inhibitors are classified as reversible, irreversible, or quasi-irreversible (also called pseudo-irreversible). Mechanism of action Organophosphates Organophosphates like TEPP, tetraethyl pyrophosphate (TEPP) and sarin inhibit cholinesterases, enzymes that hydrolyze the ...
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Phosphorofluoridates
Monofluorophosphate is an anion with the formula , which is a phosphate group with one oxygen atom substituted with a fluoride atom. The charge of the ion is −2. The ion resembles sulfate in size, shape and charge, and can thus form compounds with the same structure as sulfates. These include Tutton's salts and langbeinites. The most well-known compound of monofluorophosphate is sodium monofluorophosphate, commonly used in toothpaste. Related ions include difluorophosphate () and hexafluorophosphate (). The related neutral molecule is phosphenic fluoride . Organic derivatives can be highly toxic and include diisopropyl fluorophosphate. Some of the Novichok agents are monofluorophosphate esters. Names are given to these by naming the groups attached as esters and then adding "fluorophosphonate" to the end of the name. Two organic groups can be attached. Other related nerve gas substances may not be esters, and instead have carbon-phosphorus or nitrogen-phosphorus bonds. Th ...
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