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Hydantoin

Hydantoin

IUPAC name	imidazolidine-2,4-dione
Identifiers
CAS number	461-72-3
PubChem	10006
SMILES	C1C(=O)NC(=O)N1
Properties
Molecular formula	C₃H₄N₂O₂
Molar mass	100.076
Melting point	220°C
Solubility in water	39.7 g/L (100°C)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound that can be thought of as a cyclic "double-condensation reaction" product of glycolic acid and urea. Its chemical structure, shown in the Table of Properties at right, is similar to that of imidazolidine except that the molecule of hydantoin has carbonyl groups in the number 2 and 4 positions in the ring. Imidazolidine is the hydrogen-saturated analogue of imidazole. Imidazole is a heterocyclic aromatic organic compound.

In a more general sense, hydantoins can refer to chemical compounds that have substituent groups bonded to a hydantoin ring skeletal structure. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.^[1]

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1 Synthesis
2 Uses
3 DNA Damage
4 References

Synthesis

Hydantoin was first isolated in 1881 by Adolf von Baeyer in the course of his study of uric acid. He obtained it by hydrogenation of Allantoin, hence the name. Urech in 1873 ^[2] synthesized the derivative 5-methylhydantoin from alanine sulfate and potassium cyanate in what is now known as the Urech hydantoin synthesis:

The 5,5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate.^[3]. This reaction type is called the Bucherer-Bergs reaction.^[4]^[5]

According to the 1911 Encyclopedia Britannica, hydantoin can also be synthesized either by heating allantoin with hydroiodic acid or by "heating bromacetyl urea with alcoholic ammonia".

Uses

Chemical

When hydantoin reacts with hot, dilute hydrochloric acid, glycine is one of the products.

Medicine

Derivatives

Dantrolene is used in malignant hyperthermia, neuroleptic malignant syndrome, spasticity, and Ecstasy intoxication.

Halogenated analogues of hydantoin are used as chlorinating or brominating agents in disinfectant/sanitizer or biocide products. The three major halogenated derivatives are dichlorodimethylhydantoin (DCDMH), bromochlorodimethylhydantoin (BCDMH), and dibromodimethylhydantoin (DBDMH).

Pharmaceutical Industry

Hydantoin is used to synthesize the following anticonvulsants:

DNA Damage

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 with dealing with ancient DNA samples ^[6].

References

^ The Chemistry of the Hydantoins.Elinor Ware Chem. Rev.; 1950; 46(3) pp 403 - 470; doi:10.1021/cr60145a001
^ Urech, Ann., 165, 99 (1873).
^ Organic Syntheses, Coll. Vol. 3, p.323 (1955); Vol. 20, p.42 (1940) Link.
^ Bucherer and Steiner, J. prakt. Chem., 140, 291 (1934).
^ Bergs, Ger. pat. 566,094 (1929) [C. A., 27, 1001 (1933)].
^ Hofreiter M., Serre D., Poinar H.N., Kuch M., and Paabo S. Nature Reviews Genetics (2001) 2:353.

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.

v • d • e Anticonvulsants (N03)
Barbiturates	Barbexaclone, Metharbital, Methylphenobarbital, Pentobarbital, Phenobarbital, Primidone
Hydantoins	Ethotoin, Fosphenytoin, Mephenytoin, Phenytoin
Oxazolidinediones	Ethadione, Paramethadione, Trimethadione
Succinimides	Ethosuximide, Mesuximide, Phensuximide
Benzodiazepines	Clobazam, Clonazepam, Clorazepate, Diazepam, Lorazepam, Midazolam, Nitrazepam, Temazepam
Carboxamides	Carbamazepine, Oxcarbazepine, Rufinamide
Fatty acid derivatives	Valpromide, Valnoctamide
Carboxylic acids	Valproic acid (Sodium valproate & Valproate semisodium), Tiagabine
Others	GABA analogs: Gabapentin, Pregabalin, Progabide, Vigabatrin -- Monosaccharides: Topiramate -- Aromatic allylic alcohols: Stiripentol -- Ureas: Phenacemide, Pheneturide -- Phenyltriazines: Lamotrigine Carbamates: Emylcamate, Felbamate, Meprobamate -- Pyrrolidines: Brivaracetam, Levetiracetam, Nefiracetam, Seletracetam Sulfa drugs: Acetazolamide, Ethoxzolamide, Sultiame, Zonisamide -- Propionates: Beclamide -- Aldehydes: Paraldehyde -- Bromides: Potassium bromide, Sodium bromide

Category: Nitrogen heterocycles

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Hydantoin". A list of authors is available in Wikipedia.