xanthine

Xanthine
IUPAC name	3,7-Dihydro-purine-2,6-dione
Other names	1H-Purine-2,6-diol
Identifiers
CAS number	[69-89-6]
PubChem	1188
SMILES	O=C1NC(=O)c2[nH]cnc2N1
Properties
Molecular formula	C5H4N4O2
Molar mass	152.11 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 °C, 100 kPa) Infobox references

Xanthine (pronounced /ˈzænθiːn, ˈzænθaɪn]/), (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms. A number of mild stimulants are derived from xanthine, including caffeine and theobromine.^[1]

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.

Pathology

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

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 act as both non-selective phosphodiesterase inhibitors and adenosine receptor antagonists, with different analogues showing varying potency at the numerous subtypes, and a wide range of synthetic xanthine derivatives have been developed in order to develop compounds with greater selectivity for phosphodiesterase enzyme or adenosine receptor subtypes.^{[2][3][4][5][6][7][8][9][10][11][12][13][14]} 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

References

See also

• Murchison meteorite