All Photos(2)

C7731

Sigma-Aldrich

Caffeine

meets USP testing specifications, anhydrous

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

Quality Level

grade

anhydrous

Agency/Method

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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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

Packaging

1 kg in poly drum
250 g in poly bottle

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
Orthostatic hypotension in the elderly: diagnosis and treatment
Gupta V and Lipsitz LA
The American Journal of Medicine, 120(10), 841-847 (2007)
Metabolic effects of spices, teas, and caffeine
Westerterp-Plantenga M, et al.
Physiology & Behavior, 89(1), 85-91 (2006)
Apnea of prematurity: from cause to treatment
Zhao J, et al.
European Journal of Pediatrics, 170(9), 1097-1105 (2011)

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