Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H8N4O2.C7H4O3.2Na.H2O |
| Molecular Weight | 380.2637 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].[Na+].[O-]C(=O)C1=C([O-])C=CC=C1.CN2C=NC3=C2C(=O)NC(=O)N3C
InChI
InChIKey=MWKXONJZCRBEBM-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C7H6O3.2Na.H2O/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;8-6-4-2-1-3-5(6)7(9)10;;;/h3H,1-2H3,(H,9,12,13);1-4,8H,(H,9,10);;;1H2/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) |
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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. |
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| 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 |
|
| Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis. | 2001 |
|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
| Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects. | 2001 |
|
| Theobromine intoxication in a red fox and a European badger in Sweden. | 2001 Apr |
|
| Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats. | 2001 Aug |
|
| Continuous measurement of caffeine and two metabolites in blood and skeletal muscle of unrestrained adult horses by semi-automated in vivo microdialysis. | 2001 Dec |
|
| Minoxidil-induced hair growth is mediated by adenosine in cultured dermal papilla cells: possible involvement of sulfonylurea receptor 2B as a target of minoxidil. | 2001 Dec |
|
| Evidence for the presence of A(1) adenosine receptors in the aorta of spontaneously hypertensive rats. | 2001 Dec |
|
| Simultaneous determination of artificial sweeteners, preservatives, caffeine, theobromine and theophylline in food and pharmaceutical preparations by ion chromatography. | 2001 Dec 7 |
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| Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells. | 2001 Feb 15 |
|
| Sparks and puffs in oligodendrocyte progenitors: cross talk between ryanodine receptors and inositol trisphosphate receptors. | 2001 Jun 1 |
|
| [Simultaneous determination of various food additives by high performance liquid chromatography]. | 2001 Mar |
|
| An herbal supplement containing Ma Huang-Guarana for weight loss: a randomized, double-blind trial. | 2001 Mar |
|
| Drug diffusion mechanism through pH-sensitive hydrophobic/polyelectrolyte hydrogel membranes. | 2001 May |
|
| Caffeine-induced cardiac arrhythmia: an unrecognised danger of healthfood products. | 2001 May 21 |
|
| Nanoparticles in plant extracts--factors which influence the formation of nanoparticles in black tea infusions. | 2001 Oct |
|
| Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia. | 2001 Sep |
|
| 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 |
|
| Caffeine potentiates the discriminative-stimulus effects of nicotine in rats. | 2002 Aug |
|
| Platinum complexes of oxopurines: cis-bis(theophyllinato-N7)bis(triphenylphosphine)platinum(II) and cis-chloro(theobrominato-N1)bis(triphenylphosphine)platinum(II) ethanol hemisolvate. | 2002 Feb |
|
| Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis. | 2002 Jan |
|
| Electronic structure of some adenosine receptor antagonists. III. Quantitative investigation of the electronic absorption spectra of alkyl xanthines. | 2002 Jul |
|
| Cacao usage by the earliest Maya civilization. | 2002 Jul 18 |
|
| High-performance capillary electrophoresis analysis of mate infusions prepared from stems and leaves of Ilex paraguariensis using automated micellar electrokinetic capillary chromatography. | 2002 Jul-Aug |
|
| Enhanced analysis of purine and pyrimidine bases by the use of double-strand polyaniline coatings in micellar electrokinetic capillary chromatography. | 2002 Jun |
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| Synergistic up-regulation of vascular endothelial growth factor expression in murine macrophages by adenosine A(2A) receptor agonists and endotoxin. | 2002 Jun |
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| Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate. | 2002 Nov 20 |
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| RNA binding efficacy of theophylline, theobromine and caffeine. | 2003 Apr |
|
| Producing decaffeinated coffee plants. | 2003 Jun 19 |
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| Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors. | 2003 Mar 19 |
|
| Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin. | 2003 Nov 20 |
|
| Adenosine kinase inhibitors. 3. Synthesis, SAR, and antiinflammatory activity of a series of l-lyxofuranosyl nucleosides. | 2003 Oct 23 |
Patents
Sample Use Guides
1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration:
Oral
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| Code System | Code | Type | Description | ||
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P6VR6P4A5V
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SUB15514MIG
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100000076967
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54712690
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CHEMBL1114
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m10703
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PRIMARY | Merck Index |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
