| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:12 -0600 |
| Update Date |
2013-05-21 14:23:58 -0600 |
| HMDB ID |
HMDB02825 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Theobromine |
| Description |
Theobromine, or 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, as cited on Pubchem). Theobromine is a bitter alkaloid of the methylxanthine family, which also includes the similar compounds theophylline and caffeine. Despite its name, the compound contains no bromine. Theobromine is derived from Theobroma, the genus of the cacao tree, which is composed of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods". It is the primary alkaloid found in cocoa and chocolate, and is one of the causes for chocolate's mood-elevating effects. The amount found in chocolate is small enough that chocolate can be safely consumed by humans in large quantities, but animals that metabolize theobromine more slowly, such as cats and dogs, can easily consume enough chocolate to cause chocolate poisoning. Theobromine is a stimulant frequently confused with caffeine. Theobromine has very different effects on the human body from caffeine; it is a mild, lasting stimulant with a mood improving effect, whereas caffeine has a strong, immediate effect and increases stress. In medicine, it is used as a diuretic, vasodilator, and myocardial stimulant. There is a possible association between prostate cancer and theobromine. Theobromine is a contributing factor in acid reflux because it relaxes the esophageal sphincter muscle, allowing stomach acid access to the esophagus (Wikipedia). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Teobromin
- 2,6-Dihydroxy-3,7-dimethyl-purine
- 3,7-Dimethyl-xanthine
- Diurobromine
- Theobromine
|
| Chemical Formula |
C7H8N4O2 |
| Average Molecular Weight |
180.164 |
| Monoisotopic Molecular Weight |
180.06472552 |
| IUPAC Name |
3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
| Traditional IUPAC Name |
theobromine |
| CAS Registry Number |
83-67-0 |
| SMILES |
CN1C=NC2=C1C(=O)NC(=O)N2C |
| InChI Identifier |
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) |
| InChI Key |
YAPQBXQYLJRXSA-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Heteropolycyclic Compounds |
| Class |
Imidazopyrimidines |
| Sub Class |
Purines and Purine Derivatives |
| Other Descriptors |
- Organic Compounds
- Purine alkaloids(KEGG)
- Purinones
- a small molecule(Cyc)
- dimethylxanthine(ChEBI)
|
| Substituents |
- Imidazole
- Pyrimidine
- Pyrimidone
|
| Direct Parent |
Xanthines |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
|
| Application |
Not Available
|
| Cellular locations |
- Cytoplasm (predicted from logP)
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
357 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.33 mg/mL at 25 °C |
Not Available |
| LogP |
-0.78 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm (predicted from logP)
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.1 +/- 0.2 uM |
Adult (>18 years old) |
Male |
Normal
|
|
| Urine |
Detected but not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal
|
|
| Urine |
Detected and Quantified |
|
0.5 (0.36-0.7) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
1.3 +/- 0.5 uM |
Adult (>18 years old) |
Male |
Malaria
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.869 +/- 0.182 uM |
Adult (>18 years old) |
Both |
severe traumatic brain injury (TBI)
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.710 +/- 0.539 uM |
Not Specified |
Not Specified |
Traumatic Brain Injury (TBI)
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.641 +/- 0.169 uM |
Not Specified |
Not Specified |
Traumatic Brain Injury (TBI)
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.863 +/- 0.241 uM |
Not Specified |
Female |
Traumatic Brain Injury (TBI)
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.886 +/- 0.185 uM |
Not Specified |
Male |
Traumatic Brain Injury (TBI)
|
|
| Urine |
Detected but not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Autosomal dominant polycystic kidney disease
|
|
| Urine |
Detected and Quantified |
|
3.6 (1.0-7.3) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Asthma
|
|
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Malaria |
|---|
- Akinyinka OO, Sowunmi A, Honeywell R, Renwick AG: The effects of acute falciparum malaria on the disposition of caffeine and the comparison of saliva and plasma-derived pharmacokinetic parameters in adult Nigerians. Eur J Clin Pharmacol. 2000 May;56(2):159-65.
Pubmed: 10877011
|
| Asthma |
|---|
- Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72.
Pubmed: 15537072
|
|
| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank ID |
DB01412 |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000455 |
| KNApSAcK ID |
C00001509 |
| Chemspider ID |
5236 |
| KEGG Compound ID |
C07480 |
| BioCyc ID |
3-7-DIMETHYLXANTHINE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Theobromine |
| NuGOwiki Link |
HMDB02825 |
| Metagene Link |
HMDB02825 |
| METLIN ID |
1456 |
| PubChem Compound |
5429 |
| PDB ID |
37T |
| ChEBI ID |
28946 |
| References |
|---|
| Synthesis Reference |
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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Tserng KY, King KC, Takieddine FN: Theophylline metabolism in premature infants. Clin Pharmacol Ther. 1981 May;29(5):594-600.
Pubmed: 7214789
- Gonzalez-Jimenez J, Frutos G, Cayre I: Fluorescence quenching of human serum albumin by xanthines. Biochem Pharmacol. 1992 Aug 18;44(4):824-6.
Pubmed: 1510729
- 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.
Pubmed: 8445222
- 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.
Pubmed: 1197933
- 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.
Pubmed: 9850731
- Delahunty T, Schoendorfer D: Caffeine demethylation monitoring using a transdermal sweat patch. J Anal Toxicol. 1998 Nov-Dec;22(7):596-600.
Pubmed: 9847011
- Resman BH, Blumenthal P, Jusko WJ: Breast milk distribution of theobromine from chocolate. J Pediatr. 1977 Sep;91(3):477-80.
Pubmed: 894424
- 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.
Pubmed: 6712142
- 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.
Pubmed: 15386526
- 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.
Pubmed: 1524227
- Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8.
Pubmed: 591601
- 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.
Pubmed: 1576327
- Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55.
Pubmed: 6617078
- 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.
Pubmed: 10546928
|
Malaria
