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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2
Molecular Weight 180.1643
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE

SMILES

Cn1cnc2c1c(nc(=O)n2C)O

InChI

InChIKey=YAPQBXQYLJRXSA-UHFFFAOYSA-N
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)

HIDE SMILES / InChI

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

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
Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis.
2001
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Adenosine A(1) receptors mediate plasma exudation from the oral mucosa.
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
Evidence for the presence of A(1) adenosine receptors in the aorta of spontaneously hypertensive rats.
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
Uncertainty factors for chemical risk assessment. human variability in the pharmacokinetics of CYP1A2 probe substrates.
2001 Jul
Uncertainty factors for chemical risk assessment: interspecies differences in the in vivo pharmacokinetics and metabolism of human CYP1A2 substrates.
2001 Jul
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.
2001 Jul 6
A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle.
2001 Jun 15
[Simultaneous determination of various food additives by high performance liquid chromatography].
2001 Mar
Caffeine-induced cardiac arrhythmia: an unrecognised danger of healthfood products.
2001 May 21
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
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
Inhibition of vaccinia virus replication by adenosine in BSC-40 cells: involvement of A(2) receptor-mediated PKA activation.
2002 Jul
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
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
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
Chocolate feeding of pregnant mice influences length of limbs of their progeny.
2003
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
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
Study on the paper substrate room temperature phosphorescence of theobromine, caffeine and theophylline and analytical application.
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
Adenosine kinase inhibitors. 3. Synthesis, SAR, and antiinflammatory activity of a series of l-lyxofuranosyl nucleosides.
2003 Oct 23
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 23:44:08 UTC 2021
Edited
by admin
on Fri Jun 25 23:44:08 UTC 2021
Record UNII
OBD445WZ5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THEOBROMINE
EP   FHFI   HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
3,7-DIHYDRO-3,7-DIMETHYL-1H-PURINE-2,6-DIONE
Systematic Name English
3,7-DIMETHYLXANTHINE
Systematic Name English
THEOBROMINE [WHO-DD]
Common Name English
THEOBROMINE [MI]
Common Name English
THEOBROMINUM
HPUS  
Common Name English
FEMA NO. 3591
Code English
THEOBROMINUM [HPUS]
Common Name English
CAFFEINE MONOHYDRATE IMPURITY D [EP]
Common Name English
THEOSALVOSE
Common Name English
THEOBROMINE [FHFI]
Common Name English
SC-15090
Code English
NSC-5039
Code English
THEOBROMINE [MART.]
Common Name English
THEOBROMINE [INCI]
Common Name English
THEOBROMINE [IARC]
Common Name English
THEOBROMINE [HSDB]
Common Name English
XANTHEOSE
Common Name English
SANTHEOSE
Brand Name English
THEOBROMINE [VANDF]
Common Name English
DIUROBROMINE
Common Name English
PENTOXIFYLLINE IMPURITY A [EP]
Common Name English
THEOBROMINE [EP]
Common Name English
Classification Tree Code System Code
WHO-ATC R03DA57
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
WHO-VATC QC03BD01
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
WHO-ATC R03DA07
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
WHO-VATC QR03DA57
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
WHO-VATC QR03DA07
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
DSLD 2375 (Number of products:275)
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
NCI_THESAURUS C319
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
WHO-ATC C03BD01
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
Code System Code Type Description
EVMPD
SUB15511MIG
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
CAS
83-67-0
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
NCI_THESAURUS
C87684
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
RXCUI
10437
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2618
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL1114
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
PUBCHEM
5429
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
FDA UNII
OBD445WZ5P
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
WIKIPEDIA
THEOBROMINE
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-494-2
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
MESH
D013805
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
HSDB
7332
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
MERCK INDEX
M10703
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY Merck Index
EPA CompTox
83-67-0
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
DRUG BANK
DB01412
Created by admin on Fri Jun 25 23:44:08 UTC 2021 , Edited by admin on Fri Jun 25 23:44:08 UTC 2021
PRIMARY
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