Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H33O2.C7H7N4O2.Mg |
| Molecular Weight | 484.9145 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].CN1C=NC2=C1C(=O)[N-]C(=O)N2C.CCCCCCCC\C=C/CCCCCCCC([O-])=O
InChI
InChIKey=CMAIXUNGPMYEQR-XXAVUKJNSA-L
InChI=1S/C18H34O2.C7H8N4O2.Mg/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;/h9-10H,2-8,11-17H2,1H3,(H,19,20);3H,1-2H3,(H,9,12,13);/q;;+2/p-2/b10-9-;;
| 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 |
| Molecular Formula | C18H33O2 |
| Molecular Weight | 281.4534 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
| Molecular Formula | Mg |
| Molecular Weight | 24.305 |
| Charge | 2 |
| 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 |
|
| Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. | 1992 Apr |
|
| Continuous measurement of caffeine and two metabolites in blood and skeletal muscle of unrestrained adult horses by semi-automated in vivo microdialysis. | 2001 Dec |
|
| [Simultaneous determination of various food additives by high performance liquid chromatography]. | 2001 Mar |
|
| Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
|
| 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 |
|
| Extraction of methylxanthines from guaraná seeds, maté leaves, and cocoa beans using supercritical carbon dioxide and ethanol. | 2002 Aug 14 |
|
| Group I aptazymes as genetic regulatory switches. | 2002 Dec 4 |
|
| Electronic structure of some adenosine receptor antagonists. III. Quantitative investigation of the electronic absorption spectra of alkyl xanthines. | 2002 Jul |
|
| 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 |
|
| Selective solid-phase extraction sorbent for caffeine made by molecular imprinting. | 2002 Mar 1 |
|
| 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 |
|
| 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 |
|
| Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate. | 2002 Nov 20 |
|
| Role of extracellular ATP metabolism in regulation of platelet reactivity. | 2002 Sep |
|
| 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 |
|
| Polydeoxyribonucleotide (PDRN) promotes human osteoblast proliferation: a new proposal for bone tissue repair. | 2003 Aug 29 |
|
| Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. | 2003 Feb |
|
| Researching on new species of "Mate": Ilex brevicuspis: phytochemical and pharmacology study. | 2003 Jan |
|
| 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 |
|
| Regional differences in the adenosine A(2) receptor-mediated modulation of contractions in rat vas deferens. | 2003 Jan 24 |
|
| 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 |
|
| Producing decaffeinated coffee plants. | 2003 Jun 19 |
|
| Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors. | 2003 Mar 19 |
|
| Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants. | 2003 May |
|
| 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 |
|
| Purine alkaloids in Paullinia. | 2003 Oct |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:26:35 GMT 2023
by
admin
on
Fri Dec 15 15:26:35 GMT 2023
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| Record UNII |
3L7IL2RTM6
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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DTXSID601123817
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229-826-1
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SUB15513MIG
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3L7IL2RTM6
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100000076985
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |