Xanthine ( or , from Ancient Greek for its yellowish-white appearance; archaically xanthic acid; systematic name 3,7-dihydropurine-2,6-dione) is a purine base found in most human body tissues and fluids, as well as in other organisms. Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.
Xanthine is a product on the pathway of purine degradation. and reduce inflammation and innate immunity.
{| class="wikitable sortable"
|+ Examples of xanthine derivatives
!Name!!R<sub>1</sub>!!R<sub>2</sub>!!R<sub>3</sub>!!R<sub>8</sub>!!IUPAC nomenclature!!Found in
|-
| Xanthine||H||H||H||H||3,7-Dihydro-purine-2,6-dione||Plants, animals
|-
| 7-Methylxanthine||H||H||CH<sub>3</sub>||H||7-methyl-3H-purine-2,6-dione||Metabolite of caffeine and theobromine
|-
| Theobromine||H||CH<sub>3</sub>||CH<sub>3</sub>||H||3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione||Cacao (chocolate), yerba mate, kola, guayusa
|-
| Theophylline||CH<sub>3</sub>||CH<sub>3</sub>||H||H||1,3-Dimethyl-7H-purine-2,6-dione||Tea, cacao (chocolate), yerba mate, kola
|-
| Paraxanthine||CH<sub>3</sub>||H||CH<sub>3</sub>||H||1,7-Dimethyl-7H-purine-2,6-dione||Animals that have consumed caffeine
|-
| Caffeine||CH<sub>3</sub>||CH<sub>3</sub>||CH<sub>3</sub>||H||1,3,7-Trimethyl-1H-purine-2,6(3H,7H)-dione||Coffee, guarana, yerba mate, tea, kola, guayusa, Cacao (chocolate)
|-
| 8-Chlorotheophylline||CH<sub>3</sub>||CH<sub>3</sub>||H||Cl|| 8-Chloro-1,3-dimethyl-7H-purine-2,6-dione
| Synthetic pharmaceutical ingredient
|-
| 8-Bromotheophylline||CH<sub>3</sub>||CH<sub>3</sub>||H||Br|| 8-Bromo-1,3-dimethyl-7H-purine-2,6-dione
| Pamabrom diuretic medication
|-
|Diprophylline
|CH<sub>3</sub>
|CH<sub>3</sub>
|C<sub>3</sub>H<sub>7</sub>O<sub>2</sub>
|H
|7-(2,3-Dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
|Synthetic pharmaceutical ingredient
|-
|IBMX
|CH<sub>3</sub>
|C<sub>4</sub>H<sub>9</sub>
|H
|H
|1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
|
|-
|Uric acid
|H
|H
|H
|O
|7,9-Dihydro-1H-purine-2,6,8(3H)-trione
|Byproduct of purine nucleotides metabolism and a normal component of urine
|}
Pathology
People with rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting xanthine and related organic molecules, including the DNA and RNA components adenine and guanine, were found in outer space.
See also
- DMPX
- Murchison meteorite
- Theobromine poisoning
- Xanthene
- Xanthone
- Xanthydrol
- Kidney stone disease