U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2.C7H4O3.2Na.H2O
Molecular Weight 380.2643
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE SODIUM SALICYLATE MONOHYDRATE

SMILES

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

InChI

InChIKey=MWKXONJZCRBEBM-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C7H6O3.2Na.H2O/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);;;1H2/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 HO
Molecular Weight 17.0073
Charge -1
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

Molecular Formula C7H5O3
Molecular Weight 137.1131
Charge -1
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
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
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 20:40:24 UTC 2021
Edited
by admin
on Fri Jun 25 20:40:24 UTC 2021
Record UNII
P6VR6P4A5V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THEOBROMINE SODIUM SALICYLATE MONOHYDRATE
Systematic Name English
THEOBROMINE SODIUM SALICYLATE [JAN]
Common Name English
THEOBROMINE SODIUM SALICYLATE
JAN   MI   WHO-DD  
Systematic Name English
DIURETIN
Brand Name English
THEOBROMINE SODIUM SALICYLATE [WHO-DD]
Common Name English
EQUIMOLAR MIXTURE OF SODIUM THEOBROMINE, SODIUM SALICYLATE AND WATER
Common Name English
THEOBROMINE SODIUM SALICYLATE [MI]
Common Name English
Code System Code Type Description
FDA UNII
P6VR6P4A5V
Created by admin on Fri Jun 25 20:40:24 UTC 2021 , Edited by admin on Fri Jun 25 20:40:24 UTC 2021
PRIMARY
EVMPD
SUB15514MIG
Created by admin on Fri Jun 25 20:40:24 UTC 2021 , Edited by admin on Fri Jun 25 20:40:24 UTC 2021
PRIMARY
PUBCHEM
54712690
Created by admin on Fri Jun 25 20:40:24 UTC 2021 , Edited by admin on Fri Jun 25 20:40:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL1114
Created by admin on Fri Jun 25 20:40:24 UTC 2021 , Edited by admin on Fri Jun 25 20:40:24 UTC 2021
PRIMARY
MERCK INDEX
M10703
Created by admin on Fri Jun 25 20:40:24 UTC 2021 , Edited by admin on Fri Jun 25 20:40:24 UTC 2021
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY