Organothiophosphate Esters
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Organothiophosphate Esters
Organothiophosphates or organophosphorothioates are a subclass of organophosphorus compounds and of thiophosphate, thiophosphate compounds. They are the organic compounds that contain a phosphate group in which one or more oxygen atoms is substituted by sulfur. Many are used as pesticides, some have medical applications, and some are used as oil additives. They generally have the chemical formula (RO)3PS, [(RO)2P(S)O]−, R(RO)2PS, etc. Oligonucleotide phosphorothioates (OPS) are modified oligonucleotides where one of the oxygen atoms in the phosphate moiety is replaced by sulfur. These compounds are the basis of antisense therapy, e.g., the drugs fomivirsen (Vitravene), oblimersen, alicaforsen, and mipomersen (Kynamro). Further examples of these include: * Diazinon * Fenitrothion * Fenthion * Thiotepa Variants with P=S double bonds were developed as insecticides because of their reduced mammalian toxicity. The phosphorothioate P=S bond is converted to the toxic P=O bond in the ...
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Organophosphorus Compounds
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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Oblimersen
Oblimersen (INN, trade name Genasense; also known as Augmerosen and bcl-2 antisense oligodeoxynucleotide G3139) is an antisense oligodeoxyribonucleotide being studied as a possible treatment for several types of cancer, including chronic lymphocytic leukemia, B-cell lymphoma, and breast cancer. It may kill cancer cells by blocking the production of Bcl-2—a protein that makes cancer cells live longer—and by making them more sensitive to chemotherapy. History The antisense oligonucleotide drug oblimersen was developed by Genta Incorporated to target Bcl-2. An antisense DNA or RNA strand is non-coding and complementary to the coding strand (which is the template for producing respectively RNA or protein). An antisense drug is a short sequence of RNA which hybridises with and inactivates mRNA, preventing the protein from being formed. It was shown that the proliferation of human lymphoma cells (with t(14;18) translocation) could be inhibited by antisense RNA targeted at the st ...
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Michalski Reaction
Michalski (; feminine Michalska; plural Michalscy) is a Polish surname. It may refer to: * Adam Michalski (born 1988), Polish volleyball player * Aenne Michalsky (1908–1986), Austrian operatic soprano * Anna Jagaciak-Michalska (born 1990), Polish athlete * Arkadiusz Michalski (born 1990), Polish weightlifter * Artur Michalski (born 1962), Polish diplomat and journalist * Bożena Bednarek-Michalska (1957–2021), Polish librarian * Carl Michalski (1911–1998), German composer and conductor * Clemens Michalski (1902–1977), American politician from Milwaukee, Wisconsin * Damian Michalski (born 1998), Polish footballer * Daniel Michalski (born 2000), Polish tennis player * Darren Michalski (born 1968), rugby league player * Donald Michalski (born 1955), Canadian volleyball player * Freddy Michalski (1946–2020), French translator * Gerhard Michalski (1917–1946), German Luftwaffe pilot * Grzegorz Michalski (born 1972), Polish economist, researcher * Hans Michalsky ( ...
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Diethyl Dithiophosphoric Acid
Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the processor for production of the organophosphate insecticide Terbufos. Although samples can appear dark, it is a colorless liquid.J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2006. It is prepared by treating phosphorus pentasulfide with ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...: :P2S5 + 4 C2H5OH → 2 (C2H5O)2PS2H + H2S Reactions : Diethyl- and dimethyl dithiophosphoric acids react with bases. The results of this neutralization reaction are salts, e.g., ammonium diethyl dithiophosphate. Diethyl di ...
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Dimethyl Dithiophosphoric Acid
Dimethyl dithiophosphoric acid is the organophosphorus compound with the formula (CH3O)2PS2H. It is the processor for production of the organothiophosphate insecticide Malathion. Although samples can appear dark, the compound is a colorless, distillable liquid.J. Svara, N. Weferling, T. Hofmann "Phosphorus Compounds, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2006. It is prepared by treating phosphorus pentasulfide with methanol: Lefferts, J. L.; Molloy, K. C.; Zuckerman, J. J.; Haiduc, I.; Guta, C.; Ruse, D., "Oxy and thio phosphorus acid derivatives of tin. 1. Triorganotin(IV) dithiophosphate esters", Inorganic Chemistry 1980, volume 19, 1662-1670. :P2S5 + 4 CH3OH → 2 (CH3O)2PS2H + H2S See also * Ammonium diethyl dithiophosphate * Diethyl dithiophosphoric acid Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the proces ...
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Alcohol (chemistry)
In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugar alcohols and cholesterol. The presence of an OH group strongly modifies the properties of Hydrocarbon, hydrocarbons, conferring Hydrophile, hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur. History The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus (–287 BCE), and Pliny the Elder (23/24–79 CE). However, this did not immediately lead to the isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt. An important recognition, first found in one of the writings attributed to Jabir ibn Hayyan, J� ...
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Phosphorus Pentasulfide
Phosphorus pentasulfide is the inorganic compound with the formula (empirical) or ( molecular). This yellow solid is the one of two phosphorus sulfides of commercial value. Samples often appear greenish-gray due to impurities. It is soluble in carbon disulfide but reacts with many other solvents such as alcohols, DMSO, and DMF. Structure and synthesis Its tetrahedral molecular structure is similar to that of adamantane and almost identical to the structure of phosphorus pentoxide. Phosphorus pentasulfide is obtained by the reaction of liquid white phosphorus () with sulfur above 300 °C. The first synthesis of by Berzelius in 1843 was by this method. Alternatively, can be formed by reacting elemental sulfur or pyrite, , with ferrophosphorus, a crude form of (a byproduct of white phosphorus () production from phosphate rock): : : Applications Approximately 150,000 tons of are produced annually. The compound is mainly converted to other derivatives for us ...
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Thiotepa
Thiotepa (N,N',N''(-triethylenethiophosphoramide, INN), sold under the brand name Tepadina among others, is an anti-cancer medication. Thiotepa is an organophosphorus compound with the formula (C2H4N)3PS. History Thiotepa and its synthesis were patented in 1952 by the American Cyanamid company. It was made for use in the textile industry and in the production process of plastics. However, thiotepa entered human trials in 1953 and was found to be effective against acute myeloid leukemia, chronic myelogenous leukemia, and Hodgkin's lymphoma. The first clinical trial noted a "reasonable margin for safety" between the apparent dose and undesired bone marrow suppression In January 2007, the European Medicines Agency (EMA) designated thiotepa as an orphan drug. In April 2007, the United States FDA designated thiotepa as a conditioning treatment for use prior to hematopoietic stem cell transplantation. In June 2024, the FDA approved a ready-to-dilute liquid formulation of thiotep ...
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Fenthion
Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class.HSDB. (2003). ''Hazardous Substance Data Bank: Fenthion''. National Library of Medicine: National Toxicology Program. Available at http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB Accessed April 29, 2009.EXTOXNET. (2003). ''Pesticide information Profile for Fenthion''. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. Available at http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenthion-ext.html Accessed April 25, 2009. Uses Fenthion is a contact and stomach insecticide used against many biting insects. It is parti ...
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Fenitrothion
Fenitrothion (IUPAC name: ''O'',''O''-dimethyl ''O''-(3-methyl-4-nitrophenyl) phosphorothioate) is a phosphorothioate (organophosphate) insecticide that is inexpensive and widely used worldwide. Trade names include ''Sumithion'', a 94.2% solution of fenitrothion. Health effects Fenitrothion at sublethal doses affected the motor movement of marsupials, and at acute dose levels it reduced the energy of birds. In chronic (low) dose tests, unexpectedly only the lowest concentration (0.011 microgram/liter) of fenitrothion depressed the growth of an algae, though all of the chronic dose levels used were toxic in other ways to the algae. Just half of fenitrothion's minimally effective dose altered the thyroid structure of a freshwater murrel (the snakehead fish). Cases of non-specific encephalopathy and fatty visceral changes ( Reye's syndrome) in children living in the vicinity of fenitrothion-spraying operations invoked the research described latterly in ''Science'', and originall ...
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Diazinon
Diazinon (IUPAC name: ''O'',''O''-Diethyl ''O''- -methyl-6-(propan-2-yl)pyrimidin-2-ylphosphorothioate, INN - Dimpylate), a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company (later Novartis and then Syngenta). It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Diazinon is a major component in the "Golden Fleece" brand sheep dip. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine. Specific Health Risks: Routes of contact for D ...
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Mipomersen
Mipomersen (International Nonproprietary Name, INN; trade name Kynamro) is a drug used to treat homozygous familial hypercholesterolemia and is administered by subcutaneous injection. There is a serious risk of liver damage from this drug and it can only be prescribed in the context of a risk management plan. Indications Kynamro is used to treat homozygous familial hypercholesterolemia and is administered by injection. It cannot be freely prescribed; instead every person put on mipomersen is enrolled in a Risk Evaluation and Mitigation Strategies (REMS) program approved by the FDA. Pregnancy and lactation Mipomersen is pregnancy category B; women who are pregnant or intending to become pregnant should only use this drug if needed. It is unknown if it is secreted in human breast milk, but it was found to be secreted in the breast milk of rats. Contraindications The drug is contraindicated in people with moderate to severe liver impairment, active liver diseases, and unexp ...
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