Chemical Component Summary

NameTHEOBROMINE
Synonyms3,7-DIMETHYLXANTHINE; 3,7-DIMETHYLPURINE-2,6-DIONE
Identifiers3,7-dimethylpurine-2,6-dione
FormulaC7 H8 N4 O2
Molecular Weight180.164
TypeNON-POLYMER
Isomeric SMILESCn1cnc2c1C(=O)NC(=O)N2C
InChIInChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChIKeyYAPQBXQYLJRXSA-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count21
Chiral Atom Count0
Bond Count22
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB01412 
NameTheobromine
Groups investigational
DescriptionTheobromine (3,7-dimethylxanthine) is the principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9)
Synonyms
  • 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
  • Théobromine
  • Theobromin
  • Theobromine
  • 3,7-dimethylxanthine
Indicationtheobromine is used as a vasodilator, a diuretic, and heart stimulant. And similar to caffeine, it may be useful in management of fatigue and orthostatic hypotension.
Categories
  • Alkaloids
  • Anti-Asthmatic Agents
  • Autonomic Agents
  • Bronchodilator Agents
  • Cardiovascular Agents
ATC-Code
  • C03BD01
  • R03DA07
  • R03DA57
CAS number83-67-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Adenosine receptor A1MPPSISAFQAAYIGIEVLIALVSVPGNVLVIWAVKVNQALRDATFCFIVS...unknownantagonist
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownantagonist
cAMP-specific 3',5'-cyclic phosphodiesterase 4BMKKSRSVMTVMADDNVKDYFECSLSKSYSSSSNTLGIDLWRGRRCCSGNL...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
Cytochrome P450 2E1MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5429
ChEMBL CHEMBL1114
ChEBI CHEBI:28946
CCDC/CSD HIJYEF, HOWKUC, ZIZRUX, HIJYAB, RUTHEV01, POQHEL, ZOYBOG, MUPPOD, POQHIP, NURYUV, HOWLAJ, HOWLUD, HOWLEN, HOWLOX, CSATBR, SEDNAQ, UKOLEO
COD 1505484, 1505485, 2105789, 7218773