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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2.C7H4O3.2Na
Molecular Weight 362.249
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE SODIUM SALICYLATE ANHYDROUS

SMILES

Cn1cnc2c1c(nc(=O)n2C)[O-].c1ccc(c(c1)C(=O)O)[O-].[Na+].[Na+]

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

HIDE SMILES / InChI

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 136.1051
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H8N4O2
Molecular Weight 180.1643
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.

Originator

Sources: DOI: 10.1002/jlac.18420410117

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P30543
Gene ID: 25369.0
Gene Symbol: Adora2a
Target Organism: Rattus norvegicus (Rat)
250.0 µM [IC50]
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Thesodate

Approved Use

Theobromine was used as a diuretic and in the treatment of angina pectoris and hypertension.
Palliative
Unknown

Approved Use

Unknown
Primary
Thesodate

Approved Use

Theobromine used as a diuretic and in the treatment of angina pectoris and hypertension
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.38 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
92 μg × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
88%
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
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
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
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
Effect of adenosine A1 and A2 receptor stimulation on hypoxia-induced convulsions in adult mice.
2001 Jan-Feb
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.
2001 Jul 6
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
Salt effects on caffeine solubility, distribution, and self-association.
2002 Apr
Extraction of methylxanthines from guaraná seeds, maté leaves, and cocoa beans using supercritical carbon dioxide and ethanol.
2002 Aug 14
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
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
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
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
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
Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues.
2003 Feb
Producing decaffeinated coffee plants.
2003 Jun 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
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
Patents

Sample Use Guides

1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration: Oral
Alkaline phosphatase activity, a marker of early to mid-stage osteogenesis, was elevated in cultures of Human Mesenchymal Stem Cells that received 25 uM theobromine and reached a maximal level of stimulation at 50–100 uM theobromine.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:40:21 UTC 2021
Edited
by admin
on Fri Jun 25 20:40:21 UTC 2021
Record UNII
O42S49LAA4
Record Status Validated (UNII)
Record Version
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Name Type Language
THEOBROMINE SODIUM SALICYLATE ANHYDROUS
Common Name English
THEOBROMINE SODIUM SALICYLATE ANHYDROUS [MI]
Common Name English
EQUIMOLAR MIXTURE OF SODIUM THEOBROMINE AND SODIUM SALICYLATE
Common Name English
Code System Code Type Description
RXCUI
236926
Created by admin on Fri Jun 25 20:40:21 UTC 2021 , Edited by admin on Fri Jun 25 20:40:21 UTC 2021
PRIMARY RxNorm
FDA UNII
O42S49LAA4
Created by admin on Fri Jun 25 20:40:21 UTC 2021 , Edited by admin on Fri Jun 25 20:40:21 UTC 2021
PRIMARY
PUBCHEM
54721905
Created by admin on Fri Jun 25 20:40:21 UTC 2021 , Edited by admin on Fri Jun 25 20:40:21 UTC 2021
PRIMARY
CAS
8048-31-5
Created by admin on Fri Jun 25 20:40:21 UTC 2021 , Edited by admin on Fri Jun 25 20:40:21 UTC 2021
PRIMARY
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ACTIVE MOIETY