Aminoguanidine
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Aminoguanidine
Pimagedine, also known as aminoguanidine, is an investigational drug for the treatment of diabetic nephropathy that is no longer under development as a drug. Pimagedine functions as an inhibitor of diamine oxidase and nitric oxide synthase. It acts to reduce levels of advanced glycation end products (AGEs) through interacting with 3-deoxyglucosone, glyoxal, methylglyoxal, and related dicarbonyls. These reactive species are converted to less reactive heterocycles by this condensation reaction. History Pimagedine was under development as a drug for kidney diseases by the pharmaceutical company Alteon (now known Synvista Therapeutics Inc.) that was founded in 1986. In 1987, Alteon acquired a license to intellectual property relating to AGE inhibition from Rockefeller University. In 1989, Alteon and Marion Merrell Dow Inc (MMD) entered into a joint development program for pimagedine. In 1992, Alteon licensed a patent from Rockefeller University relating to the use of pimagedine to i ...
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Aminoguanidine Synthesis01
Pimagedine, also known as aminoguanidine, is an investigational drug for the treatment of diabetic nephropathy that is no longer under development as a drug. Pimagedine functions as an inhibitor of diamine oxidase and nitric oxide synthase. It acts to reduce levels of advanced glycation end products (AGEs) through interacting with 3-deoxyglucosone, glyoxal, methylglyoxal, and related dicarbonyls. These reactive species are converted to less reactive heterocycles by this condensation reaction. History Pimagedine was under development as a drug for kidney diseases by the pharmaceutical company Alteon (now known Synvista Therapeutics Inc.) that was founded in 1986. In 1987, Alteon acquired a license to intellectual property relating to AGE inhibition from Rockefeller University. In 1989, Alteon and Marion Merrell Dow Inc (MMD) entered into a joint development program for pimagedine. In 1992, Alteon licensed a patent from Rockefeller University relating to the use of pimagedine to in ...
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Guanidine
Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experiencing renal failure. A guanidine moiety also appears in larger organic molecules, including on the side chain of arginine. Structure Guanidine can be thought of as a nitrogenous analogue of carbonic acid. That is, the C=O group in carbonic acid is replaced by a C=NH group, and each OH is replaced by a group. Isobutene can be seen as the carbon analogue in much the same way. A detailed crystallographic analysis of guanidine was elucidated 148 years after its first synthesis, despite the simplicity of the molecule. In 2013, the positions of the hydrogen atoms and their displacement parameters were accurately determined using single-crystal neutron diffraction. Production Guanidine can be obtained from natural sources, being first isolat ...
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Diazotization
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. General properties and reactivity Arenediazonium cations and related species According to X-ray crystallography the linkage is linear in typical diazonium salts. The bond distance in benzenediazonium tetrafluoroborate is 1.083(3)  Å, which is almost identical to that for dinitrogen molecule (N≡N). The linear free energy constants σm and σp indicate that the diazonium group is strongly electron-withdrawing. Thus, the diazonio-substituted phenols and benzoic acids have greatly reduced p''K''a values compared to their unsubstituted counterparts. The p''K''a of phenolic proton of 4-hydroxybenzenediazonium is 3.4, versus 9.9 for phenol itself. In other words, the diazonium group lowers the p''K''a (enhances the acidity) by a million-fold. The stabil ...
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Tetrazene Explosive
Tetrazene (1-(5-tetrazolyl)-3-guanyl tetrazene hydrate) is an explosive material used for sensitization of priming compositions. It is a derivative of the compound with the IUPAC name tetrazene. Tetrazene is slightly more impact-sensitive than mercury fulminate. When pressed enough, its sensitivity is reduced or destroyed; this is known as dead pressing. It also decomposes in boiling water. In contact with fire, it readily explodes, producing large amounts of black smoke. It is prepared by reacting sodium nitrite with an aminoguanidine salt dissolved in acetic acid at 30–40 °C. Reactions Decomposition The decomposition of tetrazene is quite rapid around 90 °C. A sample of tetrazene was heated in an oven at 90 °C and its rate of thermal decomposition was monitored by infrared and ultraviolet spectroscopy. The thermal decomposition reaction is autocatalytic and it is likely that the same reaction can occur at even lower temperatures, however at much slower ...
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Nitrous Acid
Nitrous acid (molecular formula ) is a weak and monoprotic acid known only in Solution (chemistry), solution, in the gas phase and in the form of nitrite () salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes. Structure In the gas phase, the planar nitrous acid molecule can adopt both a ''syn'' and an ''anti'' form. The ''anti'' form predominates at room temperature, and infrared spectroscopy, IR measurements indicate it is Gibbs free energy, more stable by around 2.3 kJ/mol. p. 462. Image:Trans-nitrous-acid-2D-dimensions.png , Dimensions of the ''anti'' form(from the rotational spectroscopy, microwave spectrum) Image:Trans-nitrous-acid-3D-balls.png , ball-and-stick model, Model of the ''anti'' form Image:Cis-nitrous-acid-3D-balls.png , ''syn'' form Preparation Nitrous acid is usually generated by acidification of aqueous solutions of sodium nitrite with a mineral acid ...
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3-Amino-1,2,4-triazole
3-Amino-1,2,4-triazole (3-AT) is a heterocyclic organic compound that consists of a 1,2,4-triazole substituted with an amino group. 3-AT is a competitive inhibitor of the product of the HIS3 gene, imidazoleglycerol-phosphate dehydratase. Imidazoleglycerol-phosphate dehydratase is an enzyme catalyzing the sixth step of histidine production. 3-AT is also a nonselective systemic triazole herbicide used on nonfood croplands to control annual grasses and broadleaf and aquatic weeds. It is not used on food crops because of its carcinogenic properties. As an herbicide, it is known as ''aminotriazole'', ''amitrole'' or ''amitrol''. Amitrol was included in a biocide ban proposed by the Swedish Chemicals Agency and approved by the European Parliament on January 13, 2009. Applications in microbiology By applying 3-AT to a yeast cell culture which is dependent upon a plasmid containing HIS3 to produce histidine (i.e. its own HIS3 analogue is not present or nonfunctional), an increased lev ...
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Acetic Acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements. Acetic acid is the second simplest carboxylic acid (after formic acid). It is an important Reagent, chemical reagent and industrial chemical, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood Adhesive, glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the E number, food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats. The global ...
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Zinc
Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic table. In some respects, zinc is chemically similar to magnesium: both elements exhibit only one normal oxidation state (+2), and the Zn2+ and Mg2+ ions are of similar size.The elements are from different metal groups. See periodic table. Zinc is the 24th most abundant element in Earth's crust and has five stable isotopes. The most common zinc ore is sphalerite (zinc blende), a zinc sulfide mineral. The largest workable lodes are in Australia, Asia, and the United States. Zinc is refined by froth flotation of the ore, roasting, and final extraction using electricity ( electrowinning). Zinc is an essential trace element for humans, animals, plants and for microorganisms and is necessary for prenatal and postnatal development. It ...
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Nitroguanidine
Nitroguanidine - sometimes abbreviated NGu - is a colorless, crystalline solid that melts at 257 °C and decomposes at 254 °C. Nitroguanidine is an extremely insensitive but powerful high explosive. Wetting it with > 20 wt.-% water effects desensitization from HD 1.1 down to HD 4.1 (flammable solid). Nitroguanidine is used as an energetic material, i.e., propellant or high explosive, precursor for insecticides, and for other purposes. Manufacture Nitroguanidine is produced worldwide on a large scale starting with the reaction of dicyandiamide (DCD) with ammonium nitrate to afford the salt guanidinium nitrate, which is then nitrated by treatment with concentrated sulfuric acid at low temperature. : (NH2)3O3 → (NH2)2CNNO2 + H2O Nitroguanidine can also be generated by treatment of urea with ammonium nitrate (via the BMA process). However, owing to problems of reliability and safety, this process has never been commercialized despite its attractive economic feat ...
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