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Theobromine

Not to be confused with bromine.
Theobromine
Clinical data
Other namesxantheose
diurobromine
3,7-dimethylxanthine
3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
Dependence
liability		None
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: Unscheduled.
Pharmacokinetic data
MetabolismHepatic demethylation and oxidation
Elimination half-life6–8 hours[1][2]
ExcretionRenal (10% unchanged, rest as metabolites)
Identifiers
  • 3,7-dimethyl-1H-purine-2,6-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.359 Edit this at Wikidata
Chemical and physical data
FormulaC7H8N4O2
Molar mass180.167 g·mol−1
3D model (JSmol)
  • Cn1cnc2c1c(=O)[nH]c(=O)n2C
  • InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13) checkY
  • Key:YAPQBXQYLJRXSA-UHFFFAOYSA-N checkY
  (verify)
Theobromine
Identifiers
ECHA InfoCard 100.001.359 Edit this at Wikidata
Properties
Appearance white solid
Density 1.524 g/cm3[3]
Melting point 351 °C (664 °F; 624 K)
330 mg/L)

Theobromine, also known as xantheose, is the principal alkaloid of Theobroma cacao (cacao plant).[4] Theobromine is slightly water-soluble (330 mg/L) with a bitter taste.[5] In industry, theobromine is used as an additive and precursor to some cosmetics.[4] It is found in chocolate, as well as in a number of other foods, including tea (Camellia sinensis), some American hollies (yaupon and guayusa) and the kola nut. It is a white or colourless solid, but commercial samples can appear yellowish.[5]

  1. ^ Drouillard DD, Vesell ES, Dvorchik BH (March 1978). "Studies on theobromine disposition in normal subjects. Alterations induced by dietary abstention from or exposure to methylxanthines". Clinical Pharmacology and Therapeutics. 23 (3): 296–302. doi:10.1002/cpt1978233296. PMID 627135. S2CID 10519385.
  2. ^ Lelo A, Birkett DJ, Robson RA, Miners JO (August 1986). "Comparative pharmacokinetics of caffeine and its primary demethylated metabolites paraxanthine, theobromine and theophylline in man". British Journal of Clinical Pharmacology. 22 (2): 177–182. doi:10.1111/j.1365-2125.1986.tb05246.x. PMC 1401099. PMID 3756065.
  3. ^ Cite error: The named reference Acta was invoked but never defined (see the help page).
  4. ^ a b "Theobromine". PubChem, US National Library of Medicine. 27 August 2022. Retrieved 3 September 2022.
  5. ^ a b Smit HJ (2011). "Theobromine and the Pharmacology of Cocoa". Methylxanthines. Handbook of Experimental Pharmacology. Vol. 200. pp. 201–234. doi:10.1007/978-3-642-13443-2_7. ISBN 978-3-642-13442-5. PMID 20859797.

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