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T4500

Sigma-Aldrich

Theobromine

≥98.0%

Synonym(s):

2,6-Dihydroxy-3,7-dimethylpurine, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, 3,7-Dimethylxanthine

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About This Item

Empirical Formula (Hill Notation):
C7H8N4O2
CAS Number:
83-67-0
Molecular Weight:
180.16
Beilstein:
16464
EC Number:
201-494-2
MDL number:
MFCD00022830
UNSPSC Code:
41106305
PubChem Substance ID:
24277679
NACRES:
NA.77

Assay

≥98.0%

mp

345-350 °C

solubility

H2O: slightly soluble
aqueous base: moderately soluble
ethanol: slightly soluble

SMILES string

[H]N1C(N(C)C2=C(N(C)C=N2)C1=O)=O

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)

InChI key

YAPQBXQYLJRXSA-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290)

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General description

Theobromine is a methylxanthine alkaloid derivative, highly present in cocoa.

Application

Theobromine has been used:
  • to test in behavioural assay
  • as a food or dietary supplement
  • as a standard for theobromine quantification in brewed coffee samples

Biochem/physiol Actions

Theobromine possesses antitussive action and might be useful in treating acute and chronic cough. It is a catabolic product of caffeine and shows antioxidant and prooxidant properties.
Phosphosdiesterase inhibitor; weak adenosine receptor antagonist; diuretic; smooth muscle relaxant.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Theobromine is moderately soluble in aqueous base and is slightly soluble in water and ethanol.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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USP

USP

1631522

Sulfamethoxazole Related Compound B

Behavioral Analysis of Bitter Taste Perception in Drosophila Larvae
Kim H, et al.
Chemical Senses, 41(1), 85-94 (2016)
Development of a chromatographic low pressure flow injection system: Application to the analysis of methylxanthines in coffee
Santos JR and Antonio OSS Rangel
Analytica Chimica Acta, 715(17), 57-63 (2012)
Murat Iskar et al.
Molecular systems biology, 9, 662-662 (2013-05-02)
In pharmacology, it is crucial to understand the complex biological responses that drugs elicit in the human organism and how well they can be inferred from model organisms. We therefore identified a large set of drug-induced transcriptional modules from genome-wide
A subset of enteroendocrine cells is activated by amino acids in the Drosophila midgut
Park JH, et al.
Febs Letters (2006)
Antioxidant and prooxidant properties of caffeine, theobromine and xanthine
Azam S, et al.
Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 9(9), BR325-BR330 (2004)
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