Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H8N4O2.C7H4O3.2Na |
| Molecular Weight | 362.2484 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[O-]C(=O)C1=C([O-])C=CC=C1.CN2C=NC3=C2C(=O)NC(=O)N3C
InChI
InChIKey=KVOQALVUGACULC-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C7H6O3.2Na/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*+1/p-2
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 | 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 |
|---|---|---|
| Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. | 1999 Mar |
|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
| Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats. | 2001 Aug |
|
| 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 |
|
| Caffeine metabolism before and after liver transplantation. | 2001 Feb |
|
| 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 |
|
| Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease. | 2001 May 15 |
|
| Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats. | 2001 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Study of catechin and xanthine tea profiles as geographical tracers. | 2002 Mar 27 |
|
| 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 |
|
| 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 |
|
| RNA binding efficacy of theophylline, theobromine and caffeine. | 2003 Apr |
|
| De-intercalation of ethidium bromide and acridine orange by xanthine derivatives and their modulatory effect on anticancer agents: a study of DNA-directed toxicity enlightened by time correlated single photon counting. | 2003 Apr |
|
| Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. | 2003 Apr 15 |
|
| Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.). | 2003 Jan 16 |
|
| Intraspinal adenosine induces spinal cord norepinephrine release in spinal nerve-ligated rats but not in normal or sham controls. | 2003 Jun |
|
| Antinociceptive mechanisms of orally administered decursinol in the mouse. | 2003 Jun 13 |
|
| Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors. | 2003 Mar 19 |
|
| 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
Sat Dec 17 10:41:09 UTC 2022
by
admin
on
Sat Dec 17 10:41:09 UTC 2022
|
| Record UNII |
O42S49LAA4
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| Record Status |
Validated (UNII)
|
| Record Version |
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-
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236926
Created by
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O42S49LAA4
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54721905
Created by
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8048-31-5
Created by
admin on Sat Dec 17 10:41:09 UTC 2022 , Edited by admin on Sat Dec 17 10:41:09 UTC 2022
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |