C53

Sigma-Aldrich

Caffeine

99%

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:

assay

99%

mp

234-236.5 °C (lit.)

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

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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.

Certificate of Analysis

Certificate of Origin

Jing Li et al.
Toxicology and applied pharmacology, 284(3), 345-353 (2015-03-17)
Prenatal caffeine exposure (PCE) alters the hypothalamic-pituitary-adrenocortical (HPA) axis-associated neuroendocrine metabolic programming and induces an increased susceptibility to metabolic syndrome (MS) in intrauterine growth retardation (IUGR) offspring rats. High-fat diet (HFD) is one of the main environmental factors accounting for...
Fabrizio Ladu et al.
Behavioural brain research, 289, 48-54 (2015-04-25)
Zebrafish has been recently proposed as a valid animal model to investigate the fundamental mechanisms regulating emotional behavior and evaluate the modulatory effects exerted by psychoactive compounds. In this study, we propose a novel methodological framework based on robotics and...
Hanwen Luo et al.
Scientific reports, 5, 17746-17746 (2015-12-08)
Epidemiological investigations indicate that osteoarthritis is associated with intrauterine growth retardation (IUGR) and abnormal cholesterol metabolism. Our previous studies showed that prenatal caffeine exposure (PCE) induced chondrogenesis retardation in IUGR offspring rats. The current study sought to investigate the effects...
Christophe Provin et al.
Pharmaceutical research, 32(8), 2704-2712 (2015-03-01)
Percutaneous absorption assays of molecules for pharmaceutical and cosmetology purposes are important to determine the bioavailability of new compounds, once topically applied. The current method of choice is to measure the rate of diffusion through excised human skin using a...
Mashaalah Zarejousheghani et al.
Journal of chromatography. A, 1411, 23-33 (2015-08-11)
Acesulfame is a known indicator that is used to identify the introduction of domestic wastewater into water systems. It is negatively charged and highly water-soluble at environmental pH values. In this study, a molecularly imprinted polymer (MIP) was synthesized for...

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