Hydantoin , or glycolylurea , is a heterocyclic organic compound with the formula CH 2 C(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 groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.
10-527: Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin , used as an anticonvulsant . It was introduced approximately 10 years after phenytoin , in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic ). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients. Mephenytoin
20-454: Is a chemical structurally related to hydantoin . It is a white crystalline compound with a slight bromine and acetone odor and is insoluble in water, but soluble in acetone . BCDMH is an excellent source of both chlorine and bromine as it reacts slowly with water releasing hypochlorous acid and hypobromous acid . It used as a chemical disinfectant for recreational water sanitation and drinking water purification . BCDMH works in
30-466: Is also used in mixtures with the above. A high proportion of cytosine and thymine bases in DNA are oxidized to hydantoins over time after the death of an organism. Such modifications block DNA polymerases and thus prevents PCR from working. Such damage is a problem when dealing with ancient DNA samples. BCDMH 1-Bromo-3-chloro-5,5-dimethylhydantoin ( BCDMH or bromochlorodimethylhydantoin )
40-468: Is called the Bucherer–Bergs reaction . Hydantoin can also be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia". The cyclic structure of hydantoins was confirmed by Dorothy Hahn 1913. Of practical importance, hydantoins are obtained by condensation of a cyanohydrin with ammonium carbonate . Another useful route, which follows
50-557: Is no longer available in the US or the UK. It is still studied largely because of its interesting hydroxylation polymorphism . This anticonvulsant -related article is a stub . You can help Misplaced Pages by expanding it . Hydantoin 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
60-684: Is produced industrially via the hydantoin obtained from methional . Methylation of hydantoin yields a variety of derivatives. Dimethylhydantoin (DMH) may refer to any dimethyl derivative of hydantoin, but especially 5,5-dimethylhydantoin . Some N -halogenated derivatives of hydantoin are used as chlorinating or brominating agents in disinfectant /sanitizer or biocide products. The three major N -halogenated derivatives are dichlorodimethylhydantoin (DCDMH), bromochlorodimethylhydantoin (BCDMH), and dibromodimethylhydantoin (DBDMH). A mixed ethyl-methyl analogue, 1,3-dichloro-5-ethyl-5-methylimidazolidine-2,4-dione ( bromochloroethylmethylhydantoin ),
70-480: Is used as a muscle relaxant to treat malignant hyperthermia , neuroleptic malignant syndrome , spasticity , and ecstasy intoxication. Ropitoin is an example of an antiarrhythmic hydantoin. The hydantoin derivative Imiprothrin is a pyrethroid insecticide . Iprodione is a popular fungicide containing the hydantoin group. Hydrolysis of hydantoins affords amino acids: Hydantoin itself reacts with hot, dilute hydrochloric acid to give glycine . Methionine
80-413: The following manner: The initial BCDMH reacts with water (R = Dimethylhydantoin): Hypobromous acid partially dissociates in water: Hypobromous acid oxidizes the substrate, itself being reduced to bromide: The bromide ions are oxidized with the hypochlorous acid that was formed from the initial BCDMH: This produces more hypobromous acid; the hypochlorous acid itself act directly as a disinfectant in
90-476: 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 cyanohydrin reaction ) and ammonium carbonate . This reaction type
100-430: The work of Urech, involves the condensation of amino acids with cyanates and isocyanates: The hydantoin group can be found in several medicinally important compounds. In pharmaceuticals, hydantoin derivatives form a class of anticonvulsants ; phenytoin and fosphenytoin both contain hydantoin moieties and are both used as anticonvulsants in the treatment of seizure disorders. The hydantoin derivative dantrolene
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