Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H7N4O2.C2H3O2.2Na |
| Molecular Weight | 284.1796 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CC([O-])=O.CN1C=NC2=C1C(=O)[N-]C(=O)N2C
InChI
InChIKey=BQWXDQUPYCHWGB-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C2H4O2.2Na/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;1-2(3)4;;/h3H,1-2H3,(H,9,12,13);1H3,(H,3,4);;/q;;2*+1/p-2
Theobromine is the primary alkaloid present in the cocoa and chocolate. Theobromine is found in the shells and beans of the cacao plant and it is extracted from the husks of the bean and used for the synthesis of caffeine. Theobromine is an adenosine A1 and A2a receptor antagonist. Thesodate 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. The symptomatic adverse reactions produced by theobromine are more or less tolerable and if they become severe, they can be treated symptomatically, these include anxiety, restlessness, tremors, sleeplessness, nausea and vomiting, loss of appetite. Theobromine is currently not in use as a medicinal drug.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P30543 Gene ID: 25369.0 Gene Symbol: Adora2a Target Organism: Rattus norvegicus (Rat) |
250.0 µM [IC50] | ||
Target ID: CHEMBL318 |
120.0 µM [Ki] | ||
Target ID: P05177 Gene ID: 1544.0 Gene Symbol: CYP1A2 Target Organism: Homo sapiens (Human) |
|||
Target ID: P05181 Gene ID: 1571.0 Gene Symbol: CYP2E1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Thesodate Approved UseTheobromine was used as a diuretic and in the treatment of angina pectoris and hypertension. |
|||
| Palliative | Unknown Approved UseUnknown |
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| Primary | Thesodate Approved UseTheobromine used as a diuretic and in the treatment of angina pectoris and hypertension |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.38 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
92 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
13351 mg × min/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27662634 |
4 mg/kg bw single, intravenous dose: 4 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Equus caballus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.23 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
88% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6729831 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
THEOBROMINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. | 1992 Apr |
|
| Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. | 1999 Mar |
|
| Adenosine inhibits neutrophil vascular endothelial growth factor release and transendothelial migration via A2B receptor activation. | 2001 Apr |
|
| Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products. | 2001 Aug |
|
| Synergism between A(2A)-adenosine receptor activation and vasoactive intestinal peptide to facilitate [3H]-acetylcholine release from the rat motor nerve terminals. | 2001 Aug 24 |
|
| Continuous measurement of caffeine and two metabolites in blood and skeletal muscle of unrestrained adult horses by semi-automated in vivo microdialysis. | 2001 Dec |
|
| Effect of methylxanthine derivatives on doxorubicin transport and antitumor activity. | 2001 Dec |
|
| Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors. | 2001 Dec |
|
| Caffeine metabolism before and after liver transplantation. | 2001 Feb |
|
| Efferent arteriole tubuloglomerular feedback in the renal nephron. | 2001 Jan |
|
| Uncertainty factors for chemical risk assessment: interspecies differences in the in vivo pharmacokinetics and metabolism of human CYP1A2 substrates. | 2001 Jul |
|
| An herbal supplement containing Ma Huang-Guarana for weight loss: a randomized, double-blind trial. | 2001 Mar |
|
| Cytosolic xanthine oxidoreductase mediated bioactivation of ethanol to acetaldehyde and free radicals in rat breast tissue. Its potential role in alcohol-promoted mammary cancer. | 2001 Mar 7 |
|
| In vivo effects of adenosine A(2) receptor agonist and antagonist on neuronal and astrocytic intermediary metabolism studied with ex vivo (13)C MR spectroscopy. | 2001 Nov |
|
| Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
|
| Nanoparticles in plant extracts--factors which influence the formation of nanoparticles in black tea infusions. | 2001 Oct |
|
| Methotrexate suppresses NF-kappaB activation through inhibition of IkappaBalpha phosphorylation and degradation. | 2001 Sep 1 |
|
| Determination of theophylline by HPLC and GC-IDMS, the effect of chemically similar xanthine derivatives on the specificity of the method and the possibility of paracetamol as interfering substance. | 2002 |
|
| Salt effects on caffeine solubility, distribution, and self-association. | 2002 Apr |
|
| Group I aptazymes as genetic regulatory switches. | 2002 Dec 4 |
|
| Simultaneous determination of caffeine, theobromine, and theophylline by high-performance liquid chromatography. | 2002 Jan |
|
| Cacao usage by the earliest Maya civilization. | 2002 Jul 18 |
|
| Synergistic up-regulation of vascular endothelial growth factor expression in murine macrophages by adenosine A(2A) receptor agonists and endotoxin. | 2002 Jun |
|
| The involvement of nitric oxide on the adenosine A(2) receptor-induced cardiovascular inhibitory responses in the posterior hypothalamus of rats. | 2002 Jun 21 |
|
| Adenosine inhibits calcium channel currents via A1 receptors on salamander retinal ganglion cells in a mini-slice preparation. | 2002 May |
|
| Adenosine acts through an A3 receptor to prevent the induction of murine anti-CD3-activated killer T cells. | 2002 May 20 |
|
| Glucan stimulates human dermal fibroblast collagen biosynthesis through a nuclear factor-1 dependent mechanism. | 2002 May-Jun |
|
| Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate. | 2002 Nov 20 |
|
| Glucose-induced islet blood flow increase in rats: interaction between nervous and metabolic mediators. | 2002 Sep |
|
| Chocolate feeding of pregnant mice influences length of limbs of their progeny. | 2003 |
|
| Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. | 2003 Feb |
|
| Regional differences in the adenosine A(2) receptor-mediated modulation of contractions in rat vas deferens. | 2003 Jan 24 |
|
| Antinociceptive mechanisms of orally administered decursinol in the mouse. | 2003 Jun 13 |
|
| Study on the paper substrate room temperature phosphorescence of theobromine, caffeine and theophylline and analytical application. | 2003 May |
|
| Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin. | 2003 Nov 20 |
|
| Adenosinergic protection of dopaminergic and GABAergic neurons against mitochondrial inhibition through receptors located in the substantia nigra and striatum, respectively. | 2003 Nov 26 |
|
| Adenosine kinase inhibitors. 3. Synthesis, SAR, and antiinflammatory activity of a series of l-lyxofuranosyl nucleosides. | 2003 Oct 23 |
|
| Antioxidant and prooxidant properties of caffeine, theobromine and xanthine. | 2003 Sep |
Patents
Sample Use Guides
1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration:
Oral
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ACTIVE MOIETY
SUBSTANCE RECORD
