Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H8N4O2.C7H4O3.Ca |
| Molecular Weight | 356.347 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].[O-]C(=O)C1=CC=CC=C1[O-].CN2C=NC3=C2C(=O)NC(=O)N3C
InChI
InChIKey=UFGVUHDWEQMLGF-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C7H6O3.Ca/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);/q;;+2/p-2
| Molecular Formula | C7H4O3 |
| Molecular Weight | 136.1049 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | Ca |
| Molecular Weight | 40.078 |
| Charge | 2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C7H8N4O2 |
| Molecular Weight | 180.164 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|||
| 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 |
|---|---|---|
| Identification and quantification of drugs in human amniotic fluid. | 1975 Nov |
|
| Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis. | 2001 |
|
| Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats. | 2001 Aug |
|
| Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products. | 2001 Aug |
|
| Use of novel solid-phase extraction sorbent materials for high-performance liquid chromatography quantitation of caffeine metabolism products methylxanthines and methyluric acids in samples of biological origin. | 2001 Aug 15 |
|
| 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 |
|
| Effect of methylxanthine derivatives on doxorubicin transport and antitumor activity. | 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 |
|
| Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid. | 2001 Jan-Dec |
|
| Effect of adenosine A1 and A2 receptor stimulation on hypoxia-induced convulsions in adult mice. | 2001 Jan-Feb |
|
| Weight loss and delayed gastric emptying following a South American herbal preparation in overweight patients. | 2001 Jun |
|
| [Simultaneous determination of various food additives by high performance liquid chromatography]. | 2001 Mar |
|
| Caffeine-induced cardiac arrhythmia: an unrecognised danger of healthfood products. | 2001 May 21 |
|
| A novel analgesic compound OT-7100 attenuates nociceptive responses in animal models of inflammatory and neuropathic hyperalgesia: a possible involvement of adenosinergic anti-nociception. | 2001 Nov |
|
| Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
|
| Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats. | 2001 Oct |
|
| A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines. | 2001 Oct-Dec |
|
| Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia. | 2001 Sep |
|
| The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells. | 2001 Sep |
|
| Salt effects on caffeine solubility, distribution, and self-association. | 2002 Apr |
|
| 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 |
|
| Simultaneous determination of caffeine, theobromine, and theophylline by high-performance liquid chromatography. | 2002 Jan |
|
| Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis. | 2002 Jan |
|
| Inhibition of vaccinia virus replication by adenosine in BSC-40 cells: involvement of A(2) receptor-mediated PKA activation. | 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 |
|
| Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use. | 2002 Jun |
|
| 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 |
|
| Study of catechin and xanthine tea profiles as geographical tracers. | 2002 Mar 27 |
|
| Cocaine withdrawal severity and urine toxicology results from treatment entry predict outcome in medication trials for cocaine dependence. | 2002 Mar-Apr |
|
| Adenosine inhibits calcium channel currents via A1 receptors on salamander retinal ganglion cells in a mini-slice preparation. | 2002 May |
|
| Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain. | 2002 May |
|
| Theacrine (1,3,7,9-tetramethyluric acid) synthesis in leaves of a Chinese tea, kucha (Camellia assamica var. kucha). | 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 |
|
| Role of extracellular ATP metabolism in regulation of platelet reactivity. | 2002 Sep |
|
| Chocolate feeding of pregnant mice influences length of limbs of their progeny. | 2003 |
|
| RNA binding efficacy of theophylline, theobromine and caffeine. | 2003 Apr |
|
| 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 |
|
| Study on the paper substrate room temperature phosphorescence of theobromine, caffeine and theophylline and analytical application. | 2003 May |
|
| Adenosine A1 receptor activation reduces myocardial reperfusion effects on intrinsic cardiac nervous system. | 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 |
|
| Study on inclusion complex of cyclodextrin with methyl xanthine derivatives by fluorimetry. | 2003 Oct |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:09:42 GMT 2025
by
admin
on
Mon Mar 31 18:09:42 GMT 2025
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| Record UNII |
N5ZZ1LY24G
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Systematic Name | English | ||
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70691444
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8065-51-8
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100000076966
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m10703
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PRIMARY | Merck Index | ||
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N5ZZ1LY24G
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CHEMBL1114
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SUB15512MIG
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |