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{{Distinguish|Xanthene|Xanthan}}{{chembox| Verifiedfields = changed| verifiedrevid = 410178132| Reference = Merck Index, 11th Edition, 9968.| ImageFile = Xanthin - Xanthine.svg| ImageSize = | ImageFile2 = Xanthine-3D-balls.png| PIN = 3,7-Dihydro-1H-purine-2,6-dione| OtherNames = 1H-Purine-2,6-dione|Section1={{Chembox Identifiers| IUPHAR_ligand = 4557| Abbreviations = | InChI = 1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)| InChIKey1 = LRFVTYWOQMYALW-UHFFFAOYSA-N| InChI1 = 1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)| CASNo = 69-89-6|Diprophylline|CH3|CH3|C3H7O2|H|7-(2,3-Dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione|Synthetic pharmaceutical ingredient|IBMX|CH3|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

correct|CAS}}| EINECS = | PubChem = 1188	correct|chemspider}}| ChemSpiderID = 1151	changed|drugbank}}| DrugBank = DB02134	changed|FDA}}| UNII = 1AVZ07U9S7	changed|chemspider}}| StdInChIKey = LRFVTYWOQMYALW-UHFFFAOYSA-N| SMILES = c1[nH]c2c(n1)nc(nc2O)O	correct|EBI}}| ChEMBL = 1424	correct|chemspider}}| StdInChI = 1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)| RTECS =| MeSHName =	changed|EBI}}| ChEBI = 17712	changed|kegg}}| KEGG = C00385 }}|Section2={{Chembox Properties| Formula = C5H4N4O2| MolarMass = 152.11 g/mol| Appearance = White solid| Density = | MeltingPt = decomposes| MeltingPt_notes =| BoilingPt = | BoilingPt_notes = | Solubility = 1 g/ 14.5 L @ 16 °C1 g/1.4 L @ 100 °C| SolubleOther = | Solvent = | pKa = | pKb = }}|Section6={{Chembox Pharmacology| ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental = }}|Section7={{Chembox Hazards| MainHazards = | NFPA-H = 2| NFPA-F = 1| NFPA-R = 0| NFPA-S =| HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = }} }}Xanthine ({{IPAc-en|ˈ|z|æ|n|θ|iː|n}} or {{IPAc-en|ˈ|z|æ|n|θ|aɪ|n}}, from Ancient Greek ξανθός xanthós “yellow” due to 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.WEB, Xanthine, CID 1188,pubchem.ncbi.nlm.nih.gov/compound/1188, PubChem, National Library of Medicine, US National Institutes of Health, 28 September 2019, 2019, Several stimulants are derived from xanthine, including caffeine, theophylline, and theobromine.BOOK, Spiller, Gene A., Caffeine, CRC Press, Boca Raton, 1998, 0-8493-2647-8, BOOK, Katzung, Bertram G., Basic & Clinical Pharmacology, Paramount Publishing, 1995, 0-8385-0619-4, East Norwalk, Connecticut, 310, 311, 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. It is also created from xanthosine by purine nucleoside phosphorylase. Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme. Use and manufacturing Xanthine is used as a drug precursor for human and animal medications, and is manufactured as a pesticide ingredient. Clinical significance 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 the treatment of asthma or influenza symptoms. In contrast to other, more potent stimulants like sympathomimetic amines, xanthines mainly act to oppose the actions of adenosine, and increase alertness in the central nervous system. Toxicity Methylxanthines (methylated xanthines), which include caffeine, aminophylline, IBMX, paraxanthine, pentoxifylline, theobromine, theophylline, and 7-methylxanthine (heteroxanthine), among others, affect the airways, increase heart rate and force of contraction, and at high concentrations can cause cardiac arrhythmias. In high doses, they can lead to convulsions that are resistant to anticonvulsants. Methylxanthines induce gastric acid and pepsin secretions in the gastrointestinal tract. Methylxanthines are metabolized by cytochrome P450 in the liver.If swallowed, inhaled, or exposed to the eyes in high amounts, xanthines can be harmful, and may cause an allergic reaction if applied topically. Pharmacology In in vitro pharmacological studies, xanthines act as both: competitive nonselective phosphodiesterase inhibitors which raise intracellular cAMP, activate PKA, inhibit TNF-αJOURNAL, Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U, Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages, Am. J. Respir. Crit. Care Med., 159, 2, 508–11, February 1999, 9927365, 10.1164/ajrccm.159.2.9804085, and leukotrieneJOURNAL, Peters-Golden M, Canetti C, Mancuso P, Coffey MJ, Leukotrienes: underappreciated mediators of innate immune responses, J. Immunol., 2005, 589–94, 174, 2, 15634873, 10.4049/jimmunol.174.2.589, free, synthesis, and reduce inflammation and innate immunity and nonselective adenosine receptor antagonists JOURNAL, Daly JW, Jacobson KA, Ukena D, Adenosine receptors: development of selective agonists and antagonists, Prog Clin Biol Res, 1987, 41–63, 230, 1, 3588607, which inhibit sleepiness-inducing adenosine. However, different analogues show varying potency at the numerous subtypes, and a wide range of synthetic xanthines (some nonmethylated) have been developed searching for compounds with greater selectivity for phosphodiesterase enzyme or adenosine receptor subtypes.JOURNAL, Daly JW, Padgett WL, Shamim MT, Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors, Journal of Medicinal Chemistry, 29, 7, 1305–8, July 1986, 3806581, 10.1021/jm00157a035, JOURNAL, Daly JW, Jacobson KA, Ukena D, Adenosine receptors: development of selective agonists and antagonists, Progress in Clinical and Biological Research, 230, 41–63, 1987, 3588607, JOURNAL, Daly JW, Hide I, Müller CE, Shamim M, Caffeine analogs: structure-activity relationships at adenosine receptors, Pharmacology, 42, 6, 309–21, 1991, 1658821, 10.1159/000138813,zenodo.org/record/1235428, JOURNAL, González MP, Terán C, Teijeira M, Search for new antagonist ligands for adenosine receptors from QSAR point of view. How close are we?, Medicinal Research Reviews, 28, 3, 329–71, May 2008, 17668454, 10.1002/med.20108, 23923058, JOURNAL, Baraldi PG, Tabrizi MA, Gessi S, Borea PA, Adenosine receptor antagonists: translating medicinal chemistry and pharmacology into clinical utility, Chemical Reviews, 108, 1, 238–63, January 2008, 18181659, 10.1021/cr0682195, (File:Methylxanthine.png|alt=|left|thumb|200x200px|Xanthine: R1 = R2 = R3 = HCaffeine: R1 = R2 = R3 = CH3Theobromine: R1 = H, R2 = R3 = CH3Theophylline: R1 = R2 = CH3, R3 = H){| class=“wikitable sortable“|+ Examples of xanthine derivatives!Name!!R1!!R2!!R3!!R8!!IUPAC nomenclature!!Found in
					|Plants, animals
7-Methylxanthine>			Methyl group>CH3	H	7-methyl-3H-purine-2,6-dione	Metabolite of caffeine and theobromine
Theobromine>					H-purine-2,6-dione>	Cocoa bean>Cacao (chocolate), yerba mate, kola, guayusa
Theophylline>					H-purine-2,6-dione>	Tea, Cocoa bean>cacao (chocolate), yerba mate, kola
Paraxanthine>					H-purine-2,6-dione>|Animals that have consumed caffeine
Caffeine>					H-purine-2,6(3H,7H)-dione>	Coffee, guarana, yerba mate, tea, Kola nut>kola, guayusa, Cacao (chocolate)
8-Chlorotheophylline>				Chloride>Cl	8-Chloro-1,3-dimethyl-7H-purine-2,6-dione| Synthetic pharmaceutical ingredient
8-Bromotheophylline>				Bromide>Br	8-Bromo-1,3-dimethyl-7H-purine-2,6-dione| Pamabrom diuretic medication
Butyl group>C4H9|H|H|1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione|

{{Clear}}

Pathology

People with rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid.

Possible formation in absence of life

Studies reported in 2008, based on 12C/13C isotopic ratios of organic compounds found in the Murchison meteorite, suggested that xanthine and related chemicals, including the RNA component uracil, have been formed extraterrestrially.JOURNAL, Martins, Z., Botta, O., Fogel, M. L., Sephton, M. A., Glavin, D. P., Watson, J. S., Dworkin, J. P., Schwartz, A. W., Ehrenfreund, P., Extraterrestrial nucleobases in the Murchison meteorite, 10.1016/j.epsl.2008.03.026, Earth and Planetary Science Letters, 270, 1–2, 130–136, 2008, 2008E&PSL.270..130M, 0806.2286, 14309508, WEB, Agence France-Presse, AFP Staff, We may all be space aliens: study, 13 June 2008,afp.google.com/article/ALeqM5j_QHxWNRNdiW35Qr00L8CkwcXyvw, Agence France-Presse, AFP, 2011-08-14, dead,afp.google.com/article/ALeqM5j_QHxWNRNdiW35Qr00L8CkwcXyvw," title="web.archive.org/web/20080617213441afp.google.com/article/ALeqM5j_QHxWNRNdiW35Qr00L8CkwcXyvw,">web.archive.org/web/20080617213441afp.google.com/article/ALeqM5j_QHxWNRNdiW35Qr00L8CkwcXyvw, June 17, 2008, 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.JOURNAL, Callahan, M. P., Smith, K. E., Cleaves, H. J., Ruzicka, J., Stern, J. C., Glavin, D. P., House, C. H., Dworkin, J. P., 10.1073/pnas.1106493108, Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases, Proceedings of the National Academy of Sciences, 108, 34, 13995–8, 2011, 21836052, 3161613, 2011PNAS..10813995C, free, WEB, Steigerwald, John, NASA Researchers: DNA Building Blocks Can Be Made in Space,www.nasa.gov/topics/solarsystem/features/dna-meteorites.html, NASA, 8 August 2011, 2011-08-10, WEB, ScienceDaily Staff, DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests,www.sciencedaily.com/releases/2011/08/110808220659.htm, 9 August 2011, ScienceDaily, 2011-08-09,

See also

• DMPX
• Murchison meteorite
• Theobromine poisoning
• Xanthene
• Xanthone
• Xanthydrol
• Kidney stone disease

References

{{Reflist}}{{Stimulants}}{{Asthma and copd rx}}{{Nucleotide metabolism intermediates}}{{Adenosinergics}}