THEOBROMINE MAGNESIUM OLEATE

US Previously Marketed

First marketed in 1921

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

Structure Search

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

Description
Sources: https://www.ukessays.com/essays/sciences/obromine.php | https://www.ndrugs.com/?s=thesodate | http://www.druginfosys.com/drug.aspx?drugcode=1411&type=1 | https://www.ncbi.nlm.nih.gov/pubmed/20859797

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	Potency
Adenosine receptor A2a 15 Target ID: P30543 Gene ID: 25369.0 Gene Symbol: Adora2a Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20859797 \| https://www.ncbi.nlm.nih.gov/pubmed/6309393	Antagonist 2778	250.0 µM [IC50]
Adenosine A1 receptor 50 Target ID: CHEMBL318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6309393 \| https://www.ncbi.nlm.nih.gov/pubmed/20859797	Antagonist 2778	120.0 µM [Ki]
Cytochrome P450 1A2 72 Target ID: P05177 Gene ID: 1544.0 Gene Symbol: CYP1A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10215755	Substrate 661
Cytochrome P450 2E1 25 Target ID: P05181 Gene ID: 1571.0 Gene Symbol: CYP2E1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10215755	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 567 Sources: http://www.druginfosys.com/drug.aspx?drugcode=1411&type=1	Primary	Approved 8429	Thesodate Approved Use Theobromine was used as a diuretic and in the treatment of angina pectoris and hypertension.
Acute bronchitis 10 Sources: https://clinicaltrials.gov/ct2/show/NCT01416480 https://www.ncbi.nlm.nih.gov/pubmed/798346 https://www.ncbi.nlm.nih.gov/pubmed/20859797	Palliative	Phase III 656	Unknown Approved Use Unknown
Angina pectoris 106 Sources: Moghadasian, M.H. & Eskin, N.A.M. (2012) Functional Foods and Cardiovascular Disease, page 248, retrieved from: https://books.google.ru/books?id=RWDMBQAAQBAJ	Primary	Approved 8429	Thesodate Approved Use Theobromine used as a diuretic and in the treatment of angina pectoris and hypertension

C_max

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

T_1/2

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

F_unbound

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2E1 667 CYP1A2 1054

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1054	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2014222/	minor
CYP2E1 667	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2014222/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/19034038/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28946	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28946
ChemicalBook	CB7753381	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7753381
MolPort	MolPort-000-514-708	https://www.molport.com/shop/molecule-link/MolPort-000-514-708
Selleck Chemicals	Theobromine(3,7-Dimethylxanthine)	http://www.selleckchem.com/products/Theobromine(3,7-Dimethylxanthine).html
ZINC	ZINC000000002151	http://zinc15.docking.org/substances/ZINC000000002151
eMolecules	532231	https://www.emolecules.com/cgi-bin/more?vid=532231

PubMed

Title	Date	PubMed
Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism.	1999 Mar	10215755
Adenosine inhibits neutrophil vascular endothelial growth factor release and transendothelial migration via A2B receptor activation.	2001 Apr	11303729
Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats.	2001 Aug	11577746
Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products.	2001 Aug	11513631
Continuous measurement of caffeine and two metabolites in blood and skeletal muscle of unrestrained adult horses by semi-automated in vivo microdialysis.	2001 Dec	11903871
Simultaneous determination of artificial sweeteners, preservatives, caffeine, theobromine and theophylline in food and pharmaceutical preparations by ion chromatography.	2001 Dec 7	11765085
Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells.	2001 Feb 15	11226378
[Cerebral infarction in a patient consuming MaHuang extract and guarana].	2001 Feb 3	11229306
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001 Jan	11204934
Efferent arteriole tubuloglomerular feedback in the renal nephron.	2001 Jan	11135074
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	11195828
Effect of adenosine A1 and A2 receptor stimulation on hypoxia-induced convulsions in adult mice.	2001 Jan-Feb	11785919
Uncertainty factors for chemical risk assessment. human variability in the pharmacokinetics of CYP1A2 probe substrates.	2001 Jul	11397515
Weight loss and delayed gastric emptying following a South American herbal preparation in overweight patients.	2001 Jun	11424516
Sparks and puffs in oligodendrocyte progenitors: cross talk between ryanodine receptors and inositol trisphosphate receptors.	2001 Jun 1	11356874
[Simultaneous determination of various food additives by high performance liquid chromatography].	2001 Mar	12541649
Seizure activity and unresponsiveness after hydroxycut ingestion.	2001 May	11349754
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.	2001 May 15	11319241
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2001 Oct-Dec	11793881
Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia.	2001 Sep	11564652
Methotrexate suppresses NF-kappaB activation through inhibition of IkappaBalpha phosphorylation and degradation.	2001 Sep 1	11509639
Salt effects on caffeine solubility, distribution, and self-association.	2002 Apr	11948539
Caffeine potentiates the discriminative-stimulus effects of nicotine in rats.	2002 Aug	12172692
Enhanced analysis of purine and pyrimidine bases by the use of double-strand polyaniline coatings in micellar electrokinetic capillary chromatography.	2002 Jun	12116134
Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use.	2002 Jun	12087345
Selective solid-phase extraction sorbent for caffeine made by molecular imprinting.	2002 Mar 1	12831193
Study of catechin and xanthine tea profiles as geographical tracers.	2002 Mar 27	11902920
Adenosine acts through an A3 receptor to prevent the induction of murine anti-CD3-activated killer T cells.	2002 May 20	11992407
Glucan stimulates human dermal fibroblast collagen biosynthesis through a nuclear factor-1 dependent mechanism.	2002 May-Jun	12100377
Role of extracellular ATP metabolism in regulation of platelet reactivity.	2002 Sep	12271274
Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine.	2003 Apr 15	12604171
Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues.	2003 Feb	12602592
Intraspinal adenosine induces spinal cord norepinephrine release in spinal nerve-ligated rats but not in normal or sham controls.	2003 Jun	12766658
Producing decaffeinated coffee plants.	2003 Jun 19	12815419
Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors.	2003 Mar 19	12620503
Adenosinergic protection of dopaminergic and GABAergic neurons against mitochondrial inhibition through receptors located in the substantia nigra and striatum, respectively.	2003 Nov 26	14645494

Patents

Sample Use Guides

In Vivo Use Guide

1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily

Route of Administration: Oral

In Vitro Use Guide

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 Dec 15 15:26:35 GMT 2023` Edited by `admin` on `Fri Dec 15 15:26:35 GMT 2023`
Record UNII	3L7IL2RTM6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THEOBROMINE MAGNESIUM OLEATE

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