Theobromine

Theobromine
Identifiers
ECHA InfoCard	100.001.359
CompTox Dashboard (EPA)	DTXSID9026132 ;
Properties
Appearance	white solid
Density	1.524 g/cm3
Melting point	351 °C (664 °F; 624 K)
Solubility in water	330 mg/L)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Theobromine
Clinical data
Other names	xantheose; diurobromine; 3,7-dimethylxanthine; 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
Dependence; liability	None
Routes of; administration	Oral
ATC code	C03BD01 (WHO) R03DA07 (WHO);
Legal status
Legal status	In general: Unscheduled.;
Pharmacokinetic data
Metabolism	Hepatic demethylation and oxidation
Elimination half-life	6–8 hours
Excretion	Renal (10% unchanged, rest as metabolites)
Identifiers
	IUPAC name 3,7-dimethyl-1H-purine-2,6-dione;
CAS Number	83-67-0 ;
PubChem CID	5429;
DrugBank	DB01412 ;
ChemSpider	5236 ;
UNII	OBD445WZ5P;
KEGG	C07480 ;
ChEBI	CHEBI:28946 ;
ChEMBL	ChEMBL1114 ;
CompTox Dashboard (EPA)	DTXSID9026132 ;
ECHA InfoCard	100.001.359
Chemical and physical data
Formula	C7H8N4O2
Molar mass	180.167 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cn1cnc2c1c(=O)[nH]c(=O)n2C;
	InChI 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) ; Key:YAPQBXQYLJRXSA-UHFFFAOYSA-N ;
	(verify)

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 the leaves of the tea plant, and the kola nut. It is a white or colourless solid, but commercial samples can appear yellowish.^[5]

^ 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.
^ 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.
^ Cite error: The named reference Acta was invoked but never defined (see the help page).
^ ^a ^b "Theobromine". PubChem, US National Library of Medicine. 27 August 2022. Retrieved 3 September 2022.
^ ^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.

[halflife1-1] 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.

[halflife2-2] 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.

[Acta-3] Cite error: The named reference Acta was invoked but never defined (see the help page).

[pubchem-4] "Theobromine". PubChem, US National Library of Medicine. 27 August 2022. Retrieved 3 September 2022.

[Hbk-5] 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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Clinical data


Other names	xantheose diurobromine 3,7-dimethylxanthine 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
Dependence liability	None
Routes of administration	Oral
ATC code	C03BD01 (WHO) R03DA07 (WHO)
Legal status
Legal status	In general: Unscheduled.
Pharmacokinetic data
Metabolism	Hepatic demethylation and oxidation
Elimination half-life	6–8 hours^[1]^[2]
Excretion	Renal (10% unchanged, rest as metabolites)
Identifiers
IUPAC name 3,7-dimethyl-1H-purine-2,6-dione
CAS Number	83-67-0^Y
PubChem CID	5429
DrugBank	DB01412^Y
ChemSpider	5236^Y
UNII	OBD445WZ5P
KEGG	C07480^Y
ChEBI	CHEBI:28946^Y
ChEMBL	ChEMBL1114^Y
CompTox Dashboard (EPA)	DTXSID9026132
ECHA InfoCard	100.001.359
Chemical and physical data
Formula	C₇H₈N₄O₂
Molar mass	180.167 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Cn1cnc2c1c(=O)[nH]c(=O)n2C
InChI 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)^Y Key:YAPQBXQYLJRXSA-UHFFFAOYSA-N^Y
(verify)