Xanthine

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Xanthine
IUPAC name 3,7-Dihydro-purine-2,6-dione
Other names 1H-Purine-2,6-diol
Identifiers
CAS number 69-89-6
SMILES
Properties
Molar mass 152.111 g/mol
Appearance White solid
Melting point

decomposes

Solubility in water 1 g/ 14.5 L @ 16 °C
1 g/1.4 L @ 100 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 Â°C, 100 kPa)

Infobox references

Xanthine (IPA: /ˈzænθiËn, ˈzænθaɪn]/), (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms.

[edit] Reactions

Xanthine is a product on the pathway of purine degradation.

It is created from guanine by guanine deaminase. It is created from hypoxanthine by xanthine oxidoreductase.

Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme.

[edit] Pathology

People with the rare genetic disorder xanthinuria lack sufficient xanthine oxidase and cannot convert xanthine to uric acid.

[edit] Clinical significance of xanthine derivatives

Derivatives of xanthine, known collectively as xanthines, are a group of alkaloids commonly used for their effects as mild stimulants and as bronchodilators, notably in treating the symptoms of asthma. In contrast to other, more potent stimulants, they only inhibit the actions of sleepiness-inducing adenosine, making them somewhat less effective as stimulants than sympathomimetic amines. Due to widespread effects, the therapeutic range of xanthines is narrow, making them merely a second-line asthma treatment. The therapeutic level is 10-20 micrograms/mL blood; signs of toxicity include tremor, nausea, nervousness, and tachycardia/arrhythmia.

Methylated xanthine derivatives include caffeine, paraxanthine, theophylline, and theobromine. These drugs inhibit phosphodiesterase and antagonise adenosine. Xanthines are also found very rarely as constituents of nucleic acids.

Caffeine: R1 = R2 = R3 = CH3
Theobromine: R1 = H, R2 = R3 = CH3
Theophylline: R1 = R2 = CH3, R3 = H


Selected Xanthines
Name R1 R2 R3 IUPAC nomenclature Found In
Caffeine CH3 CH3 CH3 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione Coffee, Guarana, Yerba mate, Tea
Theobromine H CH3 CH3 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione Chocolate, Yerba mate
Theophylline CH3 CH3 H 1,3-dimethyl-7H-purine-2,6-dione Tea
Xanthine H H H 3,7-dihydro-purine-2,6-dione plants, animals


[edit] References

[edit] See also


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