C7731

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C7731

Sigma-Aldrich

 

Caffeine

meets USP testing specifications, anhydrous

Synonym:1,3,7-Trimethylxanthine
CAS Number:58-08-2
Linear Formula:C8H10N4O2
Molecular Weight:194.19
Beilstein Registry Number:17705
EC Number:200-362-1
MDL number:MFCD00005758
PubChem Substance ID:24892984

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Description

Biochem/physiol ActionsA 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.

Properties

gradeanhydrous
mp234-236.5 °C(lit.)
suitabilitymeets USP testing specifications
Gene Informationhuman ... ADORA1(134), ADORA2B(136), ADORA3(140), PDE4B(5142)
 rat ... Adora1(29290), Adora2a(25369)
 mouse ... Adora2b(11541)

Safety

Hazard CodesXn
Risk Statements22
RIDADRUN 1544 6.1/PG 3
WGK Germany1
RTECSEV6475000

References

referenceHadfield, M.G., Caffeine and the olfactory bulb. Mol. Neurobiol. 15, 31-39, (1997)
 Ferre, S., et al., Adenosine-dopamine receptor-receptor interactions as an integrative mechanism in the basal ganglia. Trends Neurosci. 20, 482-487, (1997)
 Shafer, S.H., et al., Reduced DNA synthesis and cell viability in small cell lung carcinoma by treatment with cyclic AMP phosphodiesterase inhibitors. Biochem. Pharmacol. 56, 1229-1236, (1998)
 Islam, M.S., et al., In situ activation of the type 2 ryanodine receptor in pancreatic beta cells requires cAMP-dependent phosphorylation. Proc. Natl. Acad. Sci. U. S. A. 95, 6145-6150, (1998)
 He, A.W., and Cory, J.G., p53-independent anisomycin induced G1 arrest and apoptosis in L1210 cell lines. Anticancer Res. 19, 421-428, (1999)
 Poe, B.S., and O'Neill, K.L., Caffeine modulates heat shock induced apoptosis in the human promyelocytic leukemia cell line HL-60. Cancer Lett. 121, 1-6, (1997)
 Takagi, M., et al., DNA damage-associated cell cycle and cell death control is differentially modulated by caffeine in clones with p53 mutations. Leukemia 13, 70-77, (1999)
MerckMerck 13,1636
BeilsteinBeil. 26,461 / Beil. 26,IV,2338
 Aldrich MSDS 1, 343:A / Corp MSDS 1 (1), 664:C / FT-IR 1 (2), 710:B / FT-IR 2 (3), 3668:B / IR-Spectra (2), 1120:B / IR-Spectra (3), 1287:D / NMR-Reference 2 (2), 586:A / RegBook 1 (2), 2467:A / Sax 6, 615 / Sigma FT-IR 1 (1), 581:A / Structure Index 1, 390:E:3