Pyrazolones
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Pyrazolones
Pyrazolone is 5-membered heterocycle containing two adjacent nitrogen atoms. It can be viewed as a derivative of pyrazole possessing an additional carbonyl (C=O) group. Compounds containing this functional group are useful commercially in analgesics and dyes. Structure and synthesis Pyrazolone can exist in two isomers: 3-pyrazolone and 4-pyrazolone. These isomers can interconvert via lactam–lactim and imine–enamine tautomerism; these conversion often display photochromism. For pyrazolone derivatives, the 3-pyrazolone isomer can be stabilized with ''N''-alkyl or ''N''-aryl substituents. : The first synthesis of pyrazolones was reported in 1883 by Ludwig Knorr Ludwig Knorr (2 December 1859 – 4 June 1921) was a German chemist. Together with Carl Paal, he discovered the Paal–Knorr synthesis, and the Knorr quinoline synthesis and Knorr pyrrole synthesis are also named after him. The synthesis in 1883 ..., via a condensation reaction between ethyl acetoacetate and ...
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Aminophenazone
Aminophenazone (or aminopyrine, amidopyrine, Pyramidon) is a non-narcotic analgesic substance. It is a pyrazolone and a derivative of phenazone, which also has anti-inflammatory and antipyretic properties. While inexpensive and effective, especially in the treatment of rheumatism, the drug carries a serious risk of severe and sometimes fatal side-effects, including agranulocytosis. While its production and use have been banned in many countries, including France, Thailand, India and Japan, it is still sometimes used in the developing world. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver-function tests. It is also used in measuring the total body water in the human body system. History Aminophenazone was first synthesized by Friedrich Stolz and Ludwig Knorr in the late nineteenth century, and sold as an anti-fever medicine known as Pyramidon by Hoechst AG from 1897 until its eventual replacem ...
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Propyphenazone
Propyphenazone (known as isopropylantipyrine in Japan) is a derivative of phenazone with similar analgesic and antipyretic effects. Originally patented in 1931, propyphenazone is marketed as a combination formulation with paracetamol and caffeine for treatment of primary headache disorder. Serious adverse events Case reports have described acute inferior-wall myocardial infarctions characterized by low atrial rhythms ( Kounis syndrome) secondary to propyphenazone use. Excerpt from WHO comments Banned Propyphenazone is banned in some countries including Sri Lanka, Malaysia, and Thailand. Synthesis : Ethyl 2-isopropylacetoacetate (1) and phenylhydrazine (2) are combined to form the pyrazolone ring in the intermediate (3), which is alkylated with methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to ...
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Morazone
Morazone (Novartrina, Orsimon, Rosimon-Neu, Tarcuzate) is a nonsteroidal anti-inflammatory drug (NSAID), originally developed by the German pharmaceutical company Ravensberg in the 1950s, which is used as an analgesic. It produces phenmetrazine as a major metabolite and has been reported to have been abused as a recreational drug in the past. See also * Famprofazone * Morforex Morforex (International Nonproprietary Name, INN; Bo 637), also referable to as ''N''-morpholinoethylamphetamine, is an anorectic which was never marketed. It produces amphetamine as an active metabolite. Synthesis Amphetamine is reacted with ... References {{Phenethylamines Beta-Hydroxyamphetamines Nonsteroidal anti-inflammatory drugs Norepinephrine-dopamine releasing agents Phenylmorpholines Pyrazolones Stimulants ...
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Dipyrone
Metamizole or dipyrone (informally known as the "Mexican aspirin") is a Analgesic, painkiller, Antispasmodic, spasm reliever, and Antipyretic, fever reliever drug. It is most commonly given by mouth or by intravenous infusion. It belongs to the ampyrone sulfonate family of medicines and was patented in 1922. Metamizole is marketed under various trade names. It was first used medically in Germany under the brand name "Novalgin", later becoming widely known in Slavs, Slavic nations and India under the name "Analgin". Sale of Metamizole is restricted in some jurisdictions following studies in the 1970s which correlated it to severe adverse effects, including agranulocytosis. Other studies have disputed this judgement, instead claiming that it is a safer drug than other painkillers. Metamizole is popular in many countries, where it is typically available as an Over-the-counter drug, over-the-counter medication. Medical uses Metamizole, with its potent analgesic (pain relief), ...
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Nifenazone
Nifenazone is a drug that has been used as an analgesic for a number of rheumatic conditions. Synthesis : Nifenazone is the amide formed when ampyrone and the acid chloride of nicotinic acid Nicotinic acid, or niacin, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan. Nicotinic acid is also a prescription medication. Amounts f ... are combined in a Schotten–Baumann reaction. See also * Aminopyrine References Pyrazolones Nicotinamides {{musculoskeletal-drug-stub ...
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Antipyrine
Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), antipyrin, or analgesine) is an analgesic (pain reducing), antipyretic (fever reducing) and anti-inflammatory drug. While it predates the term, it is often classified as a nonsteroidal anti-inflammatory drug (NSAID). Phenazone was one of the earliest synthetic medications — when it was patented in 1883, the only synthetic medical chemicals on the market were chloral hydrate, a sedative (as well as at least one derivative of that chemical), trimethylamine, and iodol (tetraiodopyrrol), an early antiseptic. One of the earliest widely used analgesics and antipyretics, phenazone was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen. However, it is still available in several countries either as an over-the-counter or prescribed drug. History Ludwig Knorr was the first to synthesize ph ...
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Piperylon
Piperylone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties. Synthesis : Hydrazone formation of 1-methyl-4-piperidone (1) with benzohydrazide (2) gives (3). Catalytic hydrogenation using Adams' catalyst gives the substituted hydrazine (6) after acid-catalyzed hydrolysis to remove the benzoyl group and neutralization. The pyrazolone ring is formed in a condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ... with ethyl 2-benzoylbutanoate (7), yielding piperylone. References Pyrazolones Antipyretics Nonsteroidal anti-inflammatory drugs {{analgesic-stub ...
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Edaravone
Edaravone, sold under the brand name Radicava among others, is a medication used to treat stroke and amyotrophic lateral sclerosis (ALS). It is given by intravenous infusion and by mouth. The mechanism by which edaravone might be effective is unknown. The medication is known to be an antioxidant, and oxidative stress has been hypothesized to be part of the process that kills neurons in people with ALS and in stroke victims. The most common side effects include bruising (contusions), problems walking (gait disturbances), and headaches. The U.S. Food and Drug Administration (FDA) considers it to be a first-in-class medication. Medical uses Edaravone is used to help people recover from stroke in Japan, and is used to treat ALS in the US and Japan. Adverse effects The label carries a warning about the potential for hypersensitivity reactions to edaravone, and adverse effects include bruising, gait disturbances, headache, skin inflammation, eczema, problems breathing, excess su ...
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Famprofazone
Famprofazone (Gewodin, Gewolen) is a nonsteroidal anti-inflammatory agent (NSAID) of the pyrazolone series which is available over-the-counter in some countries such as Taiwan. It has analgesic, anti-inflammatory, and antipyretic effects. Famprofazone has been known to produce methamphetamine as an active metabolite, with 15–20% of an oral dose being converted to it. As a result, famprofazone has occasionally been implicated in causing positives on drug tests for amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...s. See also * Difenamizole * Morazone References {{Phenethylamines Amines Nonsteroidal anti-inflammatory drugs Pyrazolones Stimulants Norepinephrine-dopamine releasing agents Isopropyl compounds ...
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Orange B
Orange B is a food dye from the azo dye group. It is approved by the Food and Drug Administration, United States Food and Drug Administration (FDA) for use only in hot dog and sausage casings or surfaces, up to 150 parts per million of the finished food weight. It is typically prepared as a disodium salt. Orange B was first approved by the FDA for use as a FD&C Act#Food coloring, certified food dye in 1966. However, in 1978, the FDA proposed removing it from the list of approved food additives due to concerns over potential carcinogenic contaminants, particularly the presence of 2-naphthylamine. Around the same time, its sole U.S. manufacturer, the William J. Stange Company, ceased production. Despite its non-use in food products since the late 20th century, the FDA did not formally revoke its approval. On April 22, 2025, the FDA announced plans to phase out synthetic food dyes by the end of 2026. This decision, led by FDA Commissioner Martin Makary, was driven by growing concern ...
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Mordant Red 19
Mordant red 19 is an organic compound with the chemical formula C16H13ClN4O5S. It is classified as an azo dye.Klaus Hunger, Peter Mischke, Wolfgang Rieper, Roderich Raue, Klaus Kunde, Aloys Engel: "Azo Dyes" in ''Ullmann’s Encyclopedia of Industrial Chemistry'', 2005, Wiley-VCH, Weinheim.. It is a mordant used in textile dyeing, usually in combination with chromium. It is usually found as the sodium salt. See also *Alizarin *List of colors These are the lists of colors; * List of colors: A–F * List of colors: G–M * List of colors: N–Z * List of colors (alphabetical) * List of colors by shade * List of color palettes * List of Crayola crayon colors * List of RAL colours * List o ... References External linksGoogle images of Mordant Red 19 Shades of red Azo dyes Pyrazolones Sulfonic acids Chloroarenes Phenols {{Carbohydrate-stub ...
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