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27602 Sigma-Aldrich

Caffeine

anhydrous, tested according to Ph.Eur.

Synonym: 1,3,7-Trimethylxanthine, Coffeinum

  • CAS Number 58-08-2

  • Empirical Formula (Hill Notation) C8H10N4O2

  • Molecular Weight 194.19

  •  Beilstein Registry Number 17705

  •  EC Number 200-362-1

  •  MDL number MFCD00005758

  •  PubChem Substance ID 24856687

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Properties

Related Categories 1694 Pharmaceuticals & Personal Care Products, Additional Standards, Alkaloid, Analytical Standards, Analytical/Chromatography,
grade   anhydrous
InChI Key   RYYVLZVUVIJVGH-UHFFFAOYSA-N
form   powder
pharmacopeia   testing conforms to Pharmacopeia
mp   234-236.5 °C(lit.)
solubility   H2O: soluble18.7 g/L at 16 °C
suitability   suitable for 1694 per US EPA
Gene Information   human ... ADORA1(134), ADORA2B(136), ADORA3(140), PDE4B(5142)
mouse ... Adora2b(11541)
rat ... Adora1(29290), Adora2a(25369)

Description

Other Notes

Same product — same quality — now Sigma-Aldrich brand

Application

Caffeine has been used as a radiosensitizing agent utilized for studying its impact in inhibiting the catalytic activity of ATM and ATR Kinase. CTGF is an important modulator protein of fibrogenic TGF-β. Hence, this product has also been used for examining the caffeine-dependent regulation of CTGF expression in rat hepatocytes.

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.

Caffeine is a central nervous system stimulant, adenosine receptor antagonist as well as adenosine 3′,5′-cyclic monophosphate (cAMP) phosphodiesterase inhibitor. It stimulates the sarcoplasmic reticulum (SR) Ca2+-release channel which facilitates the excitation-contraction coupling in cardiac muscle. It has also been reported to affect cellular calcium levels, releasing calcium from intracellular stores. Caffeine 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.

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
1
RTECS 
EV6475000

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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