Oxyphenisatin
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Oxyphenisatin
Oxyphenisatine (or oxyphenisatin) is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative. Natural chemical compounds similar to oxyphenisatine may be present in prunes, but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly neochlorogenic acids and chlorogenic acids) and sorbitol. Synthesis The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties. In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has cathartic In medicine, a cathartic is a subst ...
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Oxyphenisatin Synthesis
Oxyphenisatine (or oxyphenisatin) is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative. Natural chemical compounds similar to oxyphenisatine may be present in prunes, but a recent review of the relevant scientific literature suggests that the laxative effect of prunes is due to other constituents including phenolic compounds (mainly neochlorogenic acids and chlorogenic acids) and sorbitol. Synthesis The ketone group of isatin (1) is nonenolizable and has interesting properties. In strong acid it becomes protonated, and the oxygen can be replaced by electron rich moieties. In 1885, it was reported that condensation of isatin with phenol 2 leads to 3, which is Acetylated to (4). Oxyphenisatin has cathartic In medicine, a cathartic is a subst ...
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Chemical Abstracts Service
CAS (formerly Chemical Abstracts Service) is a division of the American Chemical Society. It is a source of chemical information. CAS is located in Columbus, Ohio, United States. Print periodicals ''Chemical Abstracts'' is a periodical index that provides numerous tools such as SciFinder as well as tagged keywords, summaries, indexes of disclosures, and structures of compounds in recently published scientific documents. Approximately 8,000 journals, technical reports, dissertations, conference proceedings, and new books, available in at least 50 different languages, are monitored yearly, as are patent specifications from 27 countries and two international organizations. ''Chemical Abstracts'' ceased print publication on January 1, 2010. Databases The two principal databases that support the different products are CAplus and Registry. CAS References CAS References consists of bibliographic information and abstracts for all articles in chemical journals worldwide, and chemistry-r ...
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Isatin
Isatin, also known as tribulin, is an organic compound derived from indole with formula C8H5NO2. The compound was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids. Isatin is a well-known natural product which can be found in plants of the genus ''Isatis'', in ''Couroupita guianensis'', and also in humans, as a metabolic derivative of adrenaline. It looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of biologically active compounds including antitumorals, antivirals, anti-HIVs, and antituberculars. The isatin core is also responsible for the color of “Maya blue” and “Maya yellow” dyes. Synthesis Sandmeyer methodology The Sandmeyer methodology is the oldest and straightforward way for the synthesis of isatin. The method involves the condensation between chloral hydrate and a primary arylamine (e.g. anili ...
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Lactams
A lactam is a cyclic amide, formally derived from an amino alkanoic acid. The term is a portmanteau of the words ''lactone'' + ''amide''. Nomenclature Greek prefixes in alphabetical order indicate ring size: * α-Lactam (3-atom rings) * β-Lactam (4-atom rings) * γ-Lactam (5-atom rings) * δ-Lactam (6-atom rings) * ε-Lactam (7-atom rings) This ring-size nomenclature stems from the fact that a hydrolyzed α-Lactam leads to an α-amino acid and a β-Lactam to a β-amino acid, ''etc''. Synthesis General synthetic methods exist for the organic synthesis of lactams. Beckmann rearrangement Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement. Schmidt reaction Lactams form from cyclic ketones and hydrazoic acid in the Schmidt reaction. Cyclization of amino acids Lactams can be formed from cyclisation of amino acids via the coupling between an amine and a carboxylic acid within the same molecule. Lactamization is most efficient in this wa ...
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Hepatotoxins
Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn from the market after approval. The liver plays a central role in transforming and clearing chemicals and is susceptible to the toxicity from these agents. Certain medicinal agents, when taken in overdoses (e.g. paracetamol) and sometimes even when introduced within therapeutic ranges (e.g. halothane), may injure the organ. Other chemical agents, such as those used in laboratories and industries, natural chemicals (e.g., microcystins), and herbal remedies (two prominent examples being kava, mechanism unknown, and comfrey, through its pyrrolizidine alkaloid content) can also induce hepatotoxicity. Chemicals that cause liver injury are called hepatotoxins. More than 900 drugs have been implicated in causing liver injury (see LiverTox, externa ...
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Laxatives
Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubricant and saline laxatives are used to evacuate the colon for rectal and bowel examinations, and may be supplemented by enemas under certain circumstances. Sufficiently high doses of laxatives may cause diarrhea. Some laxatives combine more than one active ingredient. Laxatives may be administered orally or rectally. Types Bulk-forming agents Bulk-forming laxatives, also known as roughage, are substances, such as fiber in food and hydrophilic agents in over-the-counter drugs, that add bulk and water to stools so that they can pass more easily through the intestines (lower part of the digestive tract). Properties * Site of action: small and large intestines * Onset of action: 12–72 hours * Examples: dietary fiber, Metamucil, C ...
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Cathartic
In medicine, a cathartic is a substance that ''accelerates'' defecation. This is similar to a laxative, which is a substance that ''eases'' defecation, usually by softening feces. It is possible for a substance to be both a laxative and a cathartic. However, agents such as psyllium seed husks increase the bulk of the feces. Cathartics such as sorbitol, magnesium citrate, magnesium sulfate, or sodium sulfate were previously used as a form of gastrointestinal decontamination following poisoning via ingestion. They are no longer routinely recommended for poisonings. High-dose cathartics may be an effective means of ridding the lower gastrointestinal tract of toxins; however, they carry a risk of electrolyte imbalances and dehydration. Catharsis can be an effect of pesticide poisonings, such as with elemental sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal ...
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Sorbitol
Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2.Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261. While similar, the two sugar alcohols have very different sources in nature, melting points, and uses. As an over-the-counter drug, sorbitol is used as a laxative to treat constipation. Synthesis Sorbitol may be synthesised via a glucose reduction reaction in ...
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Laxative
Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubricant and saline laxatives are used to evacuate the colon for rectal and bowel examinations, and may be supplemented by enemas under certain circumstances. Sufficiently high doses of laxatives may cause diarrhea. Some laxatives combine more than one active ingredient. Laxatives may be administered orally or rectally. Types Bulk-forming agents Bulk-forming laxatives, also known as roughage, are substances, such as fiber in food and hydrophilic agents in over-the-counter drugs, that add bulk and water to stools so that they can pass more easily through the intestines (lower part of the digestive tract). Properties * Site of action: small and large intestines * Onset of action: 12–72 hours * Examples: dietary fiber, Metamucil, Citru ...
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Chlorogenic Acid
Chlorogenic acid (CGA) is the ester of caffeic acid and (−)-quinic acid, functioning as an intermediate in lignin biosynthesis. The term "chlorogenic acids" refers to a related polyphenol family of esters, including hydroxycinnamic acids (caffeic acid, ferulic acid and ''p''-coumaric acid) with quinic acid. Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (khloros, light green) and -γένος (ghenos, a suffix meaning "giving rise to"), pertaining to the green color produced when chlorogenic acids are oxidized. Structural properties Structurally, chlorogenic acid is the ester formed between caffeic acid and the 3-hydroxyl of L-quinic acid. Isomers of chlorogenic acid include the caffeoyl ester at other hydroxyl sites on the quinic acid ring: 4-''O''-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA) and 5-''O''-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not ...
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