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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
Structure of THEOBROMINE MAGNESIUM OLEATE

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-;;

HIDE SMILES / InChI

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.

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 victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Effect of methylxanthine derivatives on doxorubicin transport and antitumor activity.
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
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
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
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
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
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
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
Selective solid-phase extraction sorbent for caffeine made by molecular imprinting.
2002 Mar 1
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
Glucose-induced islet blood flow increase in rats: interaction between nervous and metabolic mediators.
2002 Sep
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
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
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 Wed Jul 05 22:56:42 UTC 2023
Edited
by admin
on Wed Jul 05 22:56:42 UTC 2023
Record UNII
3L7IL2RTM6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THEOBROMINE MAGNESIUM OLEATE
WHO-DD  
Systematic Name English
OLEIC ACID, MAGNESIUM SALT, COMPD. WITH THEOBROMINE
Common Name English
ATHEMOL
Brand Name English
THMO
Common Name English
Theobromine magnesium oleate [WHO-DD]
Common Name English
MAGNESIUM 3,7-DIMETHYLXANTHINE OLEATE
Common Name English
Code System Code Type Description
CAS
6767-73-3
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID601123817
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
229-826-1
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
EVMPD
SUB15513MIG
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
PUBCHEM
76963024
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
FDA UNII
3L7IL2RTM6
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
SMS_ID
100000076985
Created by admin on Wed Jul 05 22:56:42 UTC 2023 , Edited by admin on Wed Jul 05 22:56:42 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY