THEOBROMINE (CHEM007655)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:28:39 UTC
Update Date2016-11-09 01:13:38 UTC
Accession NumberCHEM007655
Identification
Common NameTHEOBROMINE
ClassSmall Molecule
DescriptionA dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dioneChEBI
3,7-Dimethylpurine-2,6-dioneChEBI
3,7-DimethylxanthineChEBI
TheobrominChEBI
TeobrominHMDB
2,6-Dihydroxy-3,7-dimethyl-purineHMDB
3,7-Dimethyl-xanthineHMDB
DiurobromineHMDB
Chemical FormulaC7H8N4O2
Average Molecular Mass180.164 g/mol
Monoisotopic Mass180.065 g/mol
CAS Registry Number83-67-0
IUPAC Name3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Nametheobromine
SMILESCN1C=NC2=C1C(=O)NC(=O)N2C
InChI IdentifierInChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChI KeyYAPQBXQYLJRXSA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.76 g/LALOGPS
logP-0.78ALOGPS
logP-0.77ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability16.85 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0079-7980000000-efb14ee11aad17b6b4d2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-6900000000-7d44855bbf11e559d96eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0079-7980000000-efb14ee11aad17b6b4d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgr-0900000000-87a73eda89d8ce593ee8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-8d639c53ad9b2b8f508eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-0d20b5fe9b93b113a29eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-9000000000-55968ca3e94ce5a05cfeSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-001i-6900000000-7d44855bbf11e559d96eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-1900000000-1932568f11357ae32f55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-2900000000-3918185c5a4afb18f11aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0910-5900000000-b590772083f824ea0fc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9400000000-c06ac99fd6e0c84d9653Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9100000000-3802e577174b5a4accedSpectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-02a9-2900000400-2ae0058f4f5f9fc23c01Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004j-7900000000-54365e34320abc3c8f2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-599d34de0bc963388dc0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-2900000000-8a0fd0cd87c35684d19fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0910-5900000000-b590772083f824ea0fc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9400000000-c06ac99fd6e0c84d9653Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9100000000-3802e577174b5a4accedSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b1202b5f491f2aaaf542Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qi-0900000000-d58a783853c528b7d126Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01b9-8900000000-d9e4a4411ab0ed3620a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-3f82b9da0450b7ae12aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-235bf01d7d7435b9fe54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9200000000-cb89e2e8ee405aba807dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-fa072bef954a047da7f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-0900000000-22f6a3f6049c3a993878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9300000000-afa55dfa675c3caec4f0Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9700000000-770b2dc556ada7d97caeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01412
HMDB IDHMDB0002825
FooDB IDFDB000455
Phenol Explorer IDNot Available
KNApSAcK IDC00001509
BiGG IDNot Available
BioCyc ID3-7-DIMETHYLXANTHINE
METLIN ID1456
PDB IDNot Available
Wikipedia LinkTheobromine
Chemspider ID5236
ChEBI ID28946
PubChem Compound ID5429
Kegg Compound IDC07480
YMDB IDNot Available
ECMDB IDM2MDB005811
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10456233
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11600064
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16979558
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18632476
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18964243
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19018565
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21839757
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21871761
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22751681
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22824731
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22866022
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23094271
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23236361
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=9468592
17. Yoon, Hye-Sung; Hwang, In-Gyun; Bang, Won-Gi. Production of theobromine from caffeine by Pseudomonas sp. Chayon Chawon Nonjip (1995), 35(1), 33-39.
18. Tserng KY, King KC, Takieddine FN: Theophylline metabolism in premature infants. Clin Pharmacol Ther. 1981 May;29(5):594-600.
19. Gonzalez-Jimenez J, Frutos G, Cayre I: Fluorescence quenching of human serum albumin by xanthines. Biochem Pharmacol. 1992 Aug 18;44(4):824-6.
20. Holstege A, Kurz M, Weinbeck M, Gerok W: Excretion of caffeine and its primary degradation products into bile. J Hepatol. 1993 Jan;17(1):67-73.
21. Sommer KR, Hill RM, Horning MG: Identification and quantification of drugs in human amniotic fluid. Res Commun Chem Pathol Pharmacol. 1975 Nov;12(3):583-95.
22. Skopinska-Rozewska E, Janik P, Przybyszewska M, Sommer E, Bialas-Chromiec B: Inhibitory effect of theobromine on induction of angiogenesis and VEGF mRNA expression in v-raf transfectants of human urothelial cells HCV-29. Int J Mol Med. 1998 Dec;2(6):649-52.
23. Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600.
24. Resman BH, Blumenthal P, Jusko WJ: Breast milk distribution of theobromine from chocolate. J Pediatr. 1977 Sep;91(3):477-80.
25. Scott NR, Chakraborty J, Marks V: Determination of caffeine, theophylline and theobromine in serum and saliva using high-performance liquid chromatography. Ann Clin Biochem. 1984 Mar;21 ( Pt 2):120-4.
26. Emara S: Simultaneous determination of caffeine, theophylline and theobromine in human plasma by on-line solid-phase extraction coupled to reversed-phase chromatography. Biomed Chromatogr. 2004 Oct;18(8):479-85.
27. Gennaro MC, Abrigo C, Biglino P: Quantification of theophylline in human plasma by reversed-phase ion-interaction high-performance liquid chromatography and comparison with the TDx fluorescence polarization immunoassay procedure. Analyst. 1992 Jul;117(7):1071-4.
28. Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8.
29. Blanchard J, Weber CW, Shearer LE: Methylxanthine levels in breast milk of lactating women of different ethnic and socioeconomic classes. Biopharm Drug Dispos. 1992 Apr;13(3):187-96.
30. Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55.
31. Sachse C, Ruschen S, Dettling M, Schley J, Bauer S, Muller-Oerlinghausen B, Roots I, Brockmoller J: Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism. Clin Pharmacol Ther. 1999 Oct;66(4):431-8.
32. Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63.
33. Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17.
34. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.