Hydantoins
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Hydantoins
Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to a groups and a class of compounds with the same ring structure as the parent. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule. Synthesis Hydantoin was first isolated in 1861 by Adolf von Baeyer in the course of his study of uric acid. He obtained it by hydrogenation of allantoin, hence the name. : Friedrich Urech synthesized 5-methylhydantoin in 1873 from alanine sulfate and potassium cyanate in what is now known as the Urech hydantoin synthesis. The method is very similar to the modern route using alkyl and arylcyanates. The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydri ...
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Urech Hydantoin Synthesis
The Urech hydantoin synthesis is the chemical reaction of amino acids with potassium cyanate and hydrochloric acid to give hydantoins. Reaction mechanism See also *Bucherer–Bergs reaction The Bucherer–Bergs reaction is the chemical reaction of carbonyl compounds (aldehydes or ketones) or cyanohydrins with ammonium carbonate and potassium cyanide to give hydantoins. The reaction is named after Hans Theodor Bucherer. ''Overall Reac ... References {{Reflist External links English translation of 1873 German article 'on lactyl amino acids and lactyl ureas' by Friedrich Urech Condensation reactions Nitrogen heterocycle forming reactions Heterocycle forming reactions Hydantoins Name reactions ...
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Dantrolene
Dantrolene sodium, sold under the brand name Dantrium among others, is a postsynaptic muscle relaxant that lessens excitation-contraction coupling in muscle cells. It achieves this by inhibiting Ca2+ ions release from sarcoplasmic reticulum stores by antagonizing ryanodine receptors. It is the primary drug used for the treatment and prevention of malignant hyperthermia, a rare, life-threatening disorder triggered by general anesthesia or drugs. It is also used in the management of neuroleptic malignant syndrome, muscle spasticity (e.g. after strokes, in paraplegia, cerebral palsy, or patients with multiple sclerosis), and poisoning by 2,4-dinitrophenol or by the related compounds dinoseb and dinoterb. The most frequently occurring side effects include drowsiness, dizziness, weakness, general malaise, fatigue, and diarrhea. It is marketed by Par Pharmaceuticals LLC as Dantrium (in North America) and by Norgine BV as Dantrium, Dantamacrin, or Dantrolen (in Europe). A hospital ...
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Fosphenytoin
Fosphenytoin, also known as fosphenytoin sodium, and sold under the brand name Cerebyx among others, is a water-soluble phenytoin prodrug that is administered intravenously to deliver phenytoin, potentially more safely than intravenous phenytoin. It is used in the acute treatment of convulsive status epilepticus. Fosphenytoin was developed in 1996. On 18 November 2004, Sicor (a subsidiary of Teva) received a tentative approval letter from the United States Food and Drug Administration for a generic version of fosphenytoin. Medical uses Fosphenytoin is approved in the United States for the short-term (five days or fewer) treatment of epilepsy when more widely used means of phenytoin administration are not possible or are ill-advised, such as endotracheal intubation, status epilepticus or some other type of repeated seizures; cluster seizure, vomiting, and/or the patient is unalert or not awake or both.
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Anticonvulsants
Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder and borderline personality disorder, since many seem to act as mood stabilizers, and for the treatment of neuropathic pain. Anticonvulsants suppress the excessive rapid firing of neurons during seizures. Anticonvulsants also prevent the spread of the seizure within the brain. Conventional antiepileptic drugs may block sodium channels or enhance γ-aminobutyric acid ( GABA) function. Several antiepileptic drugs have multiple or uncertain mechanisms of action. Next to the voltage-gated sodium channels and components of the GABA system, their targets include GABAA receptors, the GAT-1 GABA transporter, and GABA transaminase. Additional targets include voltage-gated calcium channels, SV2A, and α2δ. By blocking sodium or ca ...
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Phenytoin
Phenytoin (PHT), sold under the brand name Dilantin among others, is an anti-seizure medication. It is useful for the prevention of tonic-clonic seizures (also known as grand mal seizures) and focal seizures, but not absence seizures. The intravenous form, fosphenytoin, is used for status epilepticus that does not improve with benzodiazepines. It may also be used for certain heart arrhythmias or neuropathic pain. It can be taken intravenously or by mouth. The intravenous form generally begins working within 30 minutes and is effective for roughly 24 hours. Blood levels can be measured to determine the proper dose. Common side effects include nausea, stomach pain, loss of appetite, poor coordination, increased hair growth, and enlargement of the gums. Potentially serious side effects include sleepiness, self harm, liver problems, bone marrow suppression, low blood pressure, and toxic epidermal necrolysis. There is evidence that use during pregnancy results in abnormalities ...
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Allantoin
Allantoin is a chemical compound with formula C4H6N4O3. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a major metabolic intermediate in most organisms including animals, plants and bacteria. It is produced from uric acid, which itself is a degradation product of nucleic acids, by action of urate oxidase (uricase). The occurs as a natural mineral compound ( IMA symbol Aan). History Allantoin was first isolated in 1800 by the Italian physician Michele Francesco Buniva (1761–1834) and the French chemist Louis Nicolas Vauquelin, who mistakenly believed it to be present in the amniotic fluid. In 1821, the French chemist Jean Louis Lassaigne found it in the fluid of the allantois; he called it ''"l'acide allantoique"''. In 1837, the German chemists Friedrich Wöhler and Justus Liebig synthesized it from uric acid and renamed it "allantoïn". Animals Named after the allantois (an amniote embryonic excretory organ in whic ...
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Cyanohydrin
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is , where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst: : In this reaction, the nucleophilic ion attacks the electrophilic carbonyl carbon in the ketone, followed by protonation by HCN, thereby regenerating the cyanide anion. Cyanohydrins are also prepared by displacement of sulfite by cyanide salts: : Cyanohydrins are intermediates in the Strecker amino acid synthesis. In aqueous acid, they are hydrolyzed to the α-hydroxy acid. Acetone cyanohydrins Acetone cyanohydrin, (CH3)2C(OH)CN is the cyano ...
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Drugs
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhalation, injection, smoking, ingestion, absorption via a patch on the skin, suppository, or dissolution under the tongue. In pharmacology, a drug is a chemical substance, typically of known structure, which, when administered to a living organism, produces a biological effect. A pharmaceutical drug, also called a medication or medicine, is a chemical substance used to treat, cure, prevent, or diagnose a disease or to promote well-being. Traditionally drugs were obtained through extraction from medicinal plants, but more recently also by organic synthesis. Pharmaceutical drugs may be used for a limited duration, or on a regular basis for chronic disorders. Pharmaceutical drugs are often classified into drug classes—groups of related ...
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Derivative (chemistry)
In chemistry, a derivative is a compound that is derived from a similar compound by a chemical reaction. In the past, derivative also meant a compound that ''can be imagined to'' arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms, but modern chemical language now uses the term structural analog for this meaning, thus eliminating ambiguity. The term "structural analogue" is common in organic chemistry. In biochemistry, the word is used for compounds that at least theoretically can be formed from the precursor compound. Chemical derivatives may be used to facilitate analysis. For example, melting point (MP) analysis can assist in identification of many organic compounds. A crystalline derivative may be prepared, such as a semicarbazone or 2,4-dinitrophenylhydrazone (derived from aldehydes or ketones), as a simple way of verifying the identity of the original compound, assuming that a table of derivative MP values is available ...
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Facts On File
Infobase Publishing is an American publisher of reference book titles and textbooks geared towards the North American library, secondary school, and university-level curriculum markets. Infobase operates a number of prominent imprints, including Facts On File, Films for the Humanities & Sciences, Cambridge Educational, Chelsea House (which also serves as the imprint for the special collection series, "Bloom's Literary Criticism" under the direction of literary critic Harold Bloom), and Ferguson Publishing. History The private equity firm Veronis Suhler Stevenson bought Facts on File and Chelsea House in 2005. Infobase bought Films for the Humanities & Sciences in 2007 and the ''World Almanac'' in 2009. In 2017, Infobase acquired The Mailbox lesson plans and ''Learning'' magazine. Veronis Suhler Stevenson sold Infobase to another private equity firm, Centre Lane Partners, in 2018. As well as nonfiction works in print, Infobase and its imprints publish a selection of works in di ...
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Dorothy Hahn
Dorothy Anna Hahn (1876–1950) was a lifelong educator and American professor of organic chemistry at Mount Holyoke College. Her research utilized the then newly developed technique of ultraviolet spectroscopy to study hydantoins. Biography Dorothy Hahn was born on April 9, 1876 in Philadelphia, Pennsylvania as the second of two daughters born to Mary Beaver and Carl S. Hahn, a German immigrant. She received extensive academic training in chemistry and was an instructor at numerous women's colleges across the United States. In 1908 she established her independent research group at Mount Holyoke College, publishing numerous scientific journal articles and books. In addition, Hahn worked in the private sector as an industrial chemist focusing on coal tar research. In 1941 she retired. Outside of her professional life, Dorothy enjoyed traveling and spent her summers at Noank on the Connecticut coast where she became a keen sailor. She died in 1950 at the age of 74. Education and ...
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