Xanthine

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Xanthine

Xanthine , (3,7-dihydro-purine-2,6-dione), is a purine

Purine

Purine is a heterocyclic compound aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
found in most body tissues and fluids and in other organisms. A number of mild stimulant

Stimulant

Stimulant drugs are drugs that temporarily increase alertness and awareness. They usually have increased side-effects with increased effectiveness, and the more powerful variants are therefore often prescription medicines or illegal drugs....
s are derived from xanthine, including caffeine

Caffeine

Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a psychoactive stimulant drug and a mild diuretic. Caffeine was discovered by a German chemist, Friedrich Ferdinand Runge, in 1819....
and theobromine

Theobromine

Theobromine, also known as xantheose, is a bitter alkaloid of the cacao plant, found in chocolate, as well as in a number of chocolate-free foods made from theobromine sources including the leaves of the tea plant, the kola or cola nut, and acai berries....
.

hine is a product on the pathway of purine degradation.

Xanthine is subsequently converted to uric acid

Uric acid

Uric acid is an organic compound of carbon, nitrogen, oxygen and hydrogen with the formula C5H4N4O3....
by the action of the xanthine oxidase

Xanthine oxidase

The enzyme xanthine oxidase, or XO, catalyzes the oxidation of hypoxanthine to xanthine and can further catalyze the oxidation of xanthine to uric acid....
enzyme.

le with the rare genetic disorder

Genetic disorder

A genetic disorder is an illness caused by abnormalities in genes or chromosomes. While some diseases, such as cancer, are due in part to a genetic disorders, they can also be caused by Environment factors....
xanthinuria

Xanthinuria

Xanthinuria, also known as xanthine oxidase deficiency, is a rare genetic disorder causing the accumulation of xanthine. It is caused by a deficiency of the enzyme xanthine oxidase....
lack sufficient xanthine oxidase and cannot convert xanthine to uric acid.

vatives of xanthine, known collectively as xanthines, are a group of alkaloid

Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
s commonly used for their effects as mild stimulant

Stimulant

Bronchodilator

A bronchodilator is a substance that Wiktionary:dilate#Verb the Bronchus and bronchioles, decreasing airway resistance and thereby facilitating airflow....
s, notably in treating the symptoms of asthma

Asthma

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Xanthine is a product on the pathway of purine degradation.

It is created from guanine
Guanine

Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, thymine, and uracil. In DNA, guanine is paired with cytosine....
by guanine deaminase
Guanine deaminase

Guanine deaminase is an enzyme which converts guanine to xanthine.External links...
.
It is created from hypoxanthine
Hypoxanthine

Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids where it is present in the anticodon of tRNA in the form of its nucleoside inosine....
by xanthine oxidoreductase.

Xanthine is subsequently converted to uric acid

Uric acid

Uric acid is an organic compound of carbon, nitrogen, oxygen and hydrogen with the formula C5H4N4O3....
by the action of the xanthine oxidase

Xanthine oxidase

The enzyme xanthine oxidase, or XO, catalyzes the oxidation of hypoxanthine to xanthine and can further catalyze the oxidation of xanthine to uric acid....
enzyme.

Pathology

People with the rare genetic disorder

Genetic disorder

Xanthinuria

Clinical significance of xanthine derivatives

Derivatives of xanthine, known collectively as xanthines, are a group of alkaloid

Alkaloid

Stimulant

Bronchodilator

Asthma

Asthma is a common chronic obstructive pulmonary disease, in which the Lung constrict, become inflammation, and are lined with excessive amounts of thickened mucus, often in response to one or more triggers....
. In contrast to other, more potent stimulants, they only inhibit the actions of sleepiness-inducing adenosine

Adenosine

Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule moiety via a ?-N9-glycosidic bond....
, making them somewhat less effective as stimulants than sympathomimetic amine

Sympathomimetic amine

Sympathomimetic drugs are substances that mimic the effects of the catecholamines, epinephrine , norepinephrine , and/or dopamine. Such drugs are used to treat cardiac arrest, low blood pressure, or even delay premature labor, among other things....
s. 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

Methylation

Methylation in the chemical sciences denotes the attachment or substitution of a methyl on various Substrate . This term is commonly used in chemistry, biochemistry, soil science and the biological sciences....
xanthine derivatives include caffeine

Caffeine

Paraxanthine

Paraxanthine, or 1,7-dimethylxanthine, is a dimethyl derivative of xanthine, structurally related to caffeine. Like caffeine, paraxanthine is a psychoactive central nervous system stimulant....
, theophylline

Theophylline

Theophylline, also known as dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as COPD or asthma under a variety of brand names....
, and theobromine

Theobromine

Phosphodiesterase inhibitor

A phosphodiesterase inhibitor is a medication that blocks one or more of the five subtypes of the enzyme phosphodiesterase , therefore preventing the inactivation of the intracellular second messengers, cyclic adenosine monophosphate and cyclic guanosine monophosphate , by the respective PDE subtype....
and antagonise

Receptor antagonist

A receptor antagonist is a type of receptor ligand or drug that does not provoke a biological response itself upon binding to a Receptor , but blocks or dampens agonist-mediated responses....
adenosine

Adenosine

Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule moiety via a ?-N9-glycosidic bond....
. Xanthines are also found very rarely as constituents of nucleic acid

Nucleic acid

A nucleic acid is a macromolecule composed of chains of monomeric nucleotides. In biochemistry these molecules carry genetic information or form structures within Cell ....
s.

Selected Xanthines
Name	R¹	R²	R³	IUPAC nomenclature IUPAC nomenclature IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry ....	Found In
Caffeine Caffeine Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a psychoactive stimulant drug and a mild diuretic. Caffeine was discovered by a German chemist, Friedrich Ferdinand Runge, in 1819....	CH₃	CH₃	CH₃	1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione	Coffee Coffee Coffee is a brewed drink prepared from roasted seeds, commonly called coffee beans, of the Coffea. Caffeinated coffee has a stimulating effect in humans.... , Guarana Guarana Guarana from the Portuguese language: guaran? , Paullinia cupana , is a climbing plant in the maple family, Sapindaceae, native to the Amazon basin and especially common in Brazil.... , Yerba mate Yerba mate Yerba mate , *Ilex paraguariensis, is a species of holly native to subtropical South America in Argentina, southern Chile, eastern Paraguay, western Uruguay and southern Brazil.... , Tea Tea Tea* refers to the agricultural products of the leaves, leaf buds, and internodes of the Camellia sinensis plant, prepared and cured by various methods....
Theobromine Theobromine Theobromine, also known as xantheose, is a bitter alkaloid of the cacao plant, found in chocolate, as well as in a number of chocolate-free foods made from theobromine sources including the leaves of the tea plant, the kola or cola nut, and acai berries....	H	CH₃	CH₃	3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione	Chocolate Chocolate Chocolate comprises a number of raw and processed foods that are produced from the seed of the tropical cacao tree.Chocolate has become one of the most popular flavors in the world.... , Yerba mate Yerba mate Yerba mate , *Ilex paraguariensis*, is a species of holly native to subtropical South America in Argentina, southern Chile, eastern Paraguay, western Uruguay and southern Brazil....
Theophylline Theophylline Theophylline, also known as dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as COPD or asthma under a variety of brand names....	CH₃	CH₃	H	1,3-dimethyl-7H-purine-2,6-dione	Tea Tea Tea refers to the agricultural products of the leaves, leaf buds, and internodes of the Camellia sinensis plant, prepared and cured by various methods....
Xanthine Xanthine Xanthine , , 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....	H	H	H	3,7-dihydro-purine-2,6-dione	plants, animals

Xanthine

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Pathology

Clinical significance of xanthine derivatives

See also