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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
Gene Symbol: Adora2a
Target Organism: Rattus norvegicus (Rat)
250 µM [IC50]
120 µM [Ki]
Target ID: P05177
Gene ID: 1544
Gene Symbol: CYP1A2
Target Organism: Homo sapiens (Human)
Target ID: P05181
Gene ID: 1571
Gene Symbol: CYP2E1
Target Organism: Homo sapiens (Human)
Conditions
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
Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism.
1999 Oct
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
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
Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine.
2001 Dec
Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells.
2001 Feb 15
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.
2001 Jan
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001 Jan
Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999).
2001 Jan 15
Protection by aspirin of indomethacin-induced small intestinal damage in rats: mediation by salicylic acid.
2001 Jan-Dec
An herbal supplement containing Ma Huang-Guarana for weight loss: a randomized, double-blind trial.
2001 Mar
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.
2001 May 15
A novel analgesic compound OT-7100 attenuates nociceptive responses in animal models of inflammatory and neuropathic hyperalgesia: a possible involvement of adenosinergic anti-nociception.
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
Group I aptazymes as genetic regulatory switches.
2002 Dec 4
Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis.
2002 Jan
Electronic structure of some adenosine receptor antagonists. III. Quantitative investigation of the electronic absorption spectra of alkyl xanthines.
2002 Jul
Cacao usage by the earliest Maya civilization.
2002 Jul 18
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
Study of catechin and xanthine tea profiles as geographical tracers.
2002 Mar 27
Cocaine withdrawal severity and urine toxicology results from treatment entry predict outcome in medication trials for cocaine dependence.
2002 Mar-Apr
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
Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate.
2002 Nov 20
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
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
Producing decaffeinated coffee plants.
2003 Jun 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
Purine alkaloids in Paullinia.
2003 Oct
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
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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
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY