P-Phenetidine
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P-Phenetidine
''p''-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO. It is one of the three isomers of phenetidine. It is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin. ''p''-Phenetidine is a metabolite of the pharmaceutical drugs bucetin and phenacetin and of the preservative ethoxyquin Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest (under commercial names such as "Stop-Scald"). It is used as a preservative in some pet food .... It is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, and ethoxyquin. ''p''-Phenetidine has high renal toxicity and it is believed to be responsible for the adverse effects that led to the withdrawal of phenacetin and bucetin from pharmaceutical use. ''p''-Phenetidine is also a possible mutagen. It is used in the synthesis of Phenacai ...
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Dulcin
Dulcin is an artificial sweetener about 250 times sweeter than sugar, discovered in 1883 by the Polish chemist Józef (Joseph) Berlinerblau (27 August 1859 – 1935). It was first mass-produced about seven years later. Although it was discovered only five years after saccharin, it never enjoyed the latter compound's market success. Nevertheless, it was an important sweetener of the early 20th century and had an advantage over saccharin in that it did not possess a bitter aftertaste. Early medical tests marked the substance as safe for human consumption, and it was considered ideal for diabetics. However, an FDA study in 1951 raised many questions about its safety, resulting in its removal from the market in 1954 after animal testing revealed chronic toxicity. Food and drug Safety association has also said that "Consequently, the Federal Security Administrator regards these chemicals as poisonous substances which have no place in any food". In Japan, poisoning accidents by dulcin ...
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Phenacetin
Phenacetin (acetophenetidin, ''N''-(4-ethoxyphenyl)acetamide) is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn in Canada in 1973, and by the U.S. Food and Drug Administration in 1983). History Phenacetin was introduced in 1887 in Elberfeld, Germany by German company Bayer, and was used principally as an analgesic; it was one of the first synthetic fever reducers to go on the market. It is also known historically to be one of the first non-opioid analgesics without anti-inflammatory properties. Although paracetamol was produced earlier, a historical accident saw it ignored after Joseph von Mering's assessment. Prior to World War One, Britain imported phenacetin from Germany. During the war, a team including Jocelyn Field Thorpe and Martha Annie Whiteley developed a synthesis in Britain. Known mechanism of action Phenacetin's analgesic effects ...
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Ethoxyquin
Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest (under commercial names such as "Stop-Scald"). It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments. Regulation Ethoxyquin was developed by Monsanto in the 1950s. Ethoxyquin was initially registered as a pesticide in 1965 as an antioxidant used as a deterrent of scald in pears through post-harvest indoor application via a drench and/or impregnated wrap. As an antioxidant to control the browning of pears, ethoxyquin is approved in the United States and in the European Union. In the United States, it is approved for use as an animal feed additive and is limited as a food additive to use only in the spices chili powder, paprika, and ground chili. Ethoxyquin is not permitted f ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which ''bonds'' between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word "isomer" () is a back-for ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which are both p ...
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Bucetin
Bucetin (INN, BAN) is an analgesic and antipyretic that is no longer marketed. Chemically, it is similar to phenacetin with which it shares the risk of carcinogenesis. Bucetin was withdrawn from use in 1986 due to renal toxicity. See also * Analgesic nephropathy * List of withdrawn drugs Drugs or medicines may be withdrawn from commercial markets because of risks to patients, but also because of commercial reasons (e.g. lack of demand and relatively high production costs). Where risks or harms is the reason for withdrawal, this w ... References Analgesics Antipyretics Anilides Withdrawn drugs {{analgesic-stub ...
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Phenacaine
Phenacaine, also known as holocaine, is a local anesthetic. It is approved for ophthalmic use. Synthesis The condensation of P-Phenetidine (1) with triethyl orthoacetate 8-39-7(2) to afford the imino ether (a so-called Pinner salt) (3). Reaction of that intermediate with a second equivalent of the aniline results (4) in a net displacement of ethanol, probably by an addition-elimination scheme. There is thus obtained the amidine, phenacaine (5). In the patented synthesis,Dr Ernst Taeuber, (1894). phenacetin Phenacetin (acetophenetidin, ''N''-(4-ethoxyphenyl)acetamide) is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn ... was used as precursor. Treatment with PCl3 gave the enol chloride, and reaction of this intermediate with p-phenetidine then completed the synthesis of phenacaine. References Local anesthetics Phenol ethers Anilines ...
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