27602

Caffeine

anhydrous, tested according to Ph. Eur.

• Synonym(s): Coffeinum, 1,3,7-Trimethylxanthine
• Empirical Formula (Hill Notation): C₈H₁₀N₄O₂
• CAS Number: 58-08-2
• Molecular Weight: 194.19
• Beilstein: 17705
• EC Number: 200-362-1
• MDL number: MFCD00005758
• UNSPSC Code: 12352210
• PubChem Substance ID: 329753004
• NACRES: NA.21
• Grade: anhydrous
• Agency: EPA 1694; USP/NF; tested according to Ph. Eur.

Properties

• grade: anhydrous
• Quality Level: 100
• Agency: EPA 1694; USP/NF; tested according to Ph. Eur.
• form: powder
• mp: 234-236.5 °C (lit.)
• solubility: H₂O: soluble 18.7 g/L at 16 °C
• application(s): environmental
• 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
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE4B(5142) ; mouse ... Adora2b(11541) ; rat ... Adora1(29290), Adora2a(25369)

Description

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

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves