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Details

Stereochemistry ACHIRAL
Molecular Formula C7H7N4O2.C6H11O7.Ca
Molecular Weight 414.381
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE CALCIUM GLUCONATE

SMILES

[Ca++].CN1C=NC2=C1C(=O)[N-]C(=O)N2C.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O

InChI

InChIKey=YUMGBTPDXDOEGH-PVBYDLIKSA-L
InChI=1S/C7H8N4O2.C6H12O7.Ca/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;7-1-2(8)3(9)4(10)5(11)6(12)13;/h3H,1-2H3,(H,9,12,13);2-5,7-11H,1H2,(H,12,13);/q;;+2/p-2/t;2-,3-,4+,5-;/m.1./s1

HIDE SMILES / InChI

Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C6H10O7
Molecular Weight 194.1394
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Identification and quantification of drugs in human amniotic fluid.
1975 Nov
Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats.
2001 Aug
Adenosine A(1) receptors mediate plasma exudation from the oral mucosa.
2001 Aug
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
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
Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors.
2001 Dec
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
Effect of adenosine A1 and A2 receptor stimulation on hypoxia-induced convulsions in adult mice.
2001 Jan-Feb
Seizure activity and unresponsiveness after hydroxycut ingestion.
2001 May
Caffeine-induced cardiac arrhythmia: an unrecognised danger of healthfood products.
2001 May 21
Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver.
2001 Nov-Dec
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.
2001 Oct-Dec
Methotrexate suppresses NF-kappaB activation through inhibition of IkappaBalpha phosphorylation and degradation.
2001 Sep 1
Caffeine potentiates the discriminative-stimulus effects of nicotine in rats.
2002 Aug
Group I aptazymes as genetic regulatory switches.
2002 Dec 4
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
Simultaneous determination of caffeine, theobromine, and theophylline by high-performance liquid chromatography.
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
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
Selective solid-phase extraction sorbent for caffeine made by molecular imprinting.
2002 Mar 1
Glucan stimulates human dermal fibroblast collagen biosynthesis through a nuclear factor-1 dependent mechanism.
2002 May-Jun
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
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
Endogenous adenosine prevents post-tetanic release facilitation mediated by alpha3beta2 nicotinic autoreceptors.
2003 Mar 19
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 Mon Mar 31 17:46:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:52 GMT 2025
Record UNII
C8T5Q6L2DE
Record Status Validated (UNII)
Record Version
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Name Type Language
THEOBROMINE CALCIUM GLUCONATE
Preferred Name English
Code System Code Type Description
CAS
10125-98-1
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
91826809
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
FDA UNII
C8T5Q6L2DE
Created by admin on Mon Mar 31 17:46:52 GMT 2025 , Edited by admin on Mon Mar 31 17:46:52 GMT 2025
PRIMARY
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ACTIVE MOIETY