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T4500

Sigma-Aldrich

Theobromine

≥98.0%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C7H8N4O2
Número de CAS:
83-67-0
Peso molecular:
180.16
Beilstein/REAXYS Number:
16464
EC Number:
201-494-2
MDL number:
MFCD00022830
UNSPSC Code:
41106305
PubChem Substance ID:
24277679
NACRES:
NA.77

Quality Level

200

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

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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USP

USP

1631522

Sulfamethoxazole Related Compound B

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)
Theobromine inhibits sensory nerve activation and cough
Usmani OS, et al.
Faseb Journal (2004)
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)
Behavioral Analysis of Bitter Taste Perception in Drosophila Larvae
Kim H, et al.
Chemical Senses, 41(1), 85-94 (2016)
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
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