Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H7N4O2.C6H11O7.Ca |
| Molecular Weight | 414.381 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].CN1C=NC2=C1C(=O)[N-]C(=O)N2C.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O
InChI
InChIKey=YUMGBTPDXDOEGH-PVBYDLIKSA-L
InChI=1S/C7H8N4O2.C6H12O7.Ca/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;7-1-2(8)3(9)4(10)5(11)6(12)13;/h3H,1-2H3,(H,9,12,13);2-5,7-11H,1H2,(H,12,13);/q;;+2/p-2/t;2-,3-,4+,5-;/m.1./s1
| Molecular Formula | C6H10O7 |
| Molecular Weight | 194.1394 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| 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 |
|---|---|---|
| Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis. | 2001 |
|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
| Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products. | 2001 Aug |
|
| Adenosine A(1) receptors mediate plasma exudation from the oral mucosa. | 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 |
|
| 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 |
|
| 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 |
|
| Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors. | 2001 Dec |
|
| Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine. | 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 |
|
| Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine. | 2001 Jul 6 |
|
| Weight loss and delayed gastric emptying following a South American herbal preparation in overweight patients. | 2001 Jun |
|
| 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 |
|
| 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 |
|
| Developmental variation of sugars, carboxylic acids, purine alkaloids, fatty acids, and endoproteinase activity during maturation of Theobroma cacao L. seeds. | 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 |
|
| Methotrexate suppresses NF-kappaB activation through inhibition of IkappaBalpha phosphorylation and degradation. | 2001 Sep 1 |
|
| Extraction of methylxanthines from guaraná seeds, maté leaves, and cocoa beans using supercritical carbon dioxide and ethanol. | 2002 Aug 14 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Glucose-induced islet blood flow increase in rats: interaction between nervous and metabolic mediators. | 2002 Sep |
|
| 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 |
|
| 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 |
|
| Regional differences in the adenosine A(2) receptor-mediated modulation of contractions in rat vas deferens. | 2003 Jan 24 |
|
| 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 |
|
| Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin. | 2003 Nov 20 |
|
| 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
Fri Dec 16 16:13:21 UTC 2022
by
admin
on
Fri Dec 16 16:13:21 UTC 2022
|
| Record UNII |
C8T5Q6L2DE
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
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Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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10125-98-1
Created by
admin on Fri Dec 16 16:13:21 UTC 2022 , Edited by admin on Fri Dec 16 16:13:21 UTC 2022
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NON-SPECIFIC STOICHIOMETRY | |||
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91826809
Created by
admin on Fri Dec 16 16:13:21 UTC 2022 , Edited by admin on Fri Dec 16 16:13:21 UTC 2022
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PRIMARY | |||
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C8T5Q6L2DE
Created by
admin on Fri Dec 16 16:13:21 UTC 2022 , Edited by admin on Fri Dec 16 16:13:21 UTC 2022
|
PRIMARY |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |