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C7731

Sigma-Aldrich

Caffeine

meets USP testing specifications, anhydrous

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Synonym(s):
1,3,7-Trimethylxanthine
Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
Beilstein/REAXYS Number:
17705
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

grade

anhydrous

Quality Level

agency

USP/NF
meets USP testing specifications

form

crystalline
powder

mp

234-236.5 °C (lit.)

solubility

H2O: soluble 18.7 g/L at 16 °C

SMILES string

CN1C(=O)N(C)c2ncn(C)c2C1=O

InChI

1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChI key

RYYVLZVUVIJVGH-UHFFFAOYSA-N

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1 of 4

This Item
27602W222402W222455
vibrant-m

C7731

Caffeine

vibrant-m

27602

Caffeine

vibrant-m

W222402

Caffeine

vibrant-m

W222455

Caffeine

agency

USP/NF, meets USP testing specifications

agency

EPA 1694, USP/NF, tested according to Ph. Eur.

agency

-

agency

-

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

form

crystalline

form

powder

form

powder

form

-

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

-

Quality Level

200

Quality Level

100

Quality Level

400

Quality Level

300

General description

Caffeine is a commonly consumed pharmacologically active substance. It is a member of the class of methylxanthines. It is a natural alkaloid found in coffee, cocoa and other plants. Caffeine might be linked to osteoporosis, cardiovascular risk, arrhythmia and gastrointestinal disturbances. Caffeine is used to treat orthostatic hypotension, bronchopulmonary dysplasia and apnea of prematurity (AOP).

Application

Caffeine has been used:
  • to functionally disable Ca2+ removal via sarco/endoplasmic reticulum Ca2+ ATPase (SERCA)
  • to determine its effects in overcoming excitation-contraction-coupling failure
  • to compare its role as a stimulant with guarana

Biochem/physiol Actions

A central nervous system stimulant believed to act through adenosine receptors and monoamine neurotransmitters. It is an adenosine receptor antagonist and adenosine 3′,5′-cyclic monophosphate (cAMP) phosphodiesterase inhibitor. Thus, levels of cAMP increase in cells following treatment with caffeine. It has been reported to affect cellular calcium levels, releasing calcium from intracellular stores. It overrides the cell cycle effects of various chemicals such as protease inhibitors, preventing apoptosis; and it has been shown to inhibit cellular DNA repair mechanisms.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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There and back again: Iterating between population-based modeling and experiments reveals surprising regulation of calcium transients in rat cardiac myocytes
Devenyi RA and Sobie EA
Journal of Molecular and Cellular Cardiology, 96, 38-48 (2016)
Caffeine?s beneficial effect on maximal voluntary strength and activation in uninjured but not injured muscle
Park ND, et al.
International Journal of Sport Nutrition and Exercise Metabolism, 18(6), 639-652 (2008)
Apnea of prematurity: from cause to treatment
Zhao J, et al.
European Journal of Pediatrics, 170(9), 1097-1105 (2011)
Metabolic effects of spices, teas, and caffeine
Westerterp-Plantenga M, et al.
Physiology & Behavior, 89(1), 85-91 (2006)
Ryan A Devenyi et al.
Journal of molecular and cellular cardiology, 96, 38-48 (2015-08-04)
While many ion channels and transporters involved in cardiac cellular physiology have been identified and described, the relative importance of each in determining emergent cellular behaviors remains unclear. Here we address this issue with a novel approach that combines population-based

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