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27602

Sigma-Aldrich

Cafeína

anhydrous, tested according to Ph. Eur.

Sinônimo(s):

1,3,7-Trimetilxantina

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About This Item

Fórmula empírica (Notação de Hill):
C8H10N4O2
Número CAS:
58-08-2
Peso molecular:
194.19
Beilstein:
17705
Número CE:
200-362-1
Número MDL:
MFCD00005758
Código UNSPSC:
12352210
ID de substância PubChem:
329753004
NACRES:
NA.21

grau

anhydrous

Nível de qualidade

100

Agency

EPA 1694
USP/NF
tested according to Ph. Eur.

forma

powder

pf

234-236.5 °C (lit.)

solubilidade

H2O: soluble 18.7 g/L at 16 °C

aplicação(ões)

environmental

cadeia de caracteres SMILES

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

chave InChI

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Informações sobre genes

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140) , PDE4B(5142)
mouse ... Adora2b(11541)
rat ... Adora1(29290) , Adora2a(25369)

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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P264 - P270 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
BCCG5617
BCCD8116
BCCC9089
BCCC3983
BCCB5533

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E Rousseau et al.
The American journal of physiology, 256(2 Pt 2), H328-H333 (1989-02-01)
Caffeine is thought to affect excitation-contraction coupling in cardiac muscle by activating the sarcoplasmic reticulum (SR) Ca2+-release channel. The effect of caffeine at the single channel level was studied by incorporating canine cardiac SR vesicles into planar lipid bilayers. Cardiac
J N Sarkaria et al.
Cancer research, 59(17), 4375-4382 (1999-09-15)
Caffeine exposure sensitizes tumor cells to ionizing radiation and other genotoxic agents. The radiosensitizing effects of caffeine are associated with the disruption of multiple DNA damage-responsive cell cycle checkpoints. The similarity of these checkpoint defects to those seen in ataxia-telangiectasia
C P Selby et al.
Proceedings of the National Academy of Sciences of the United States of America, 87(9), 3522-3525 (1990-05-01)
Caffeine potentiates the mutagenic and lethal effects of genotoxic agents. It is thought that this is due, at least in some organisms, to inhibition of DNA repair. However, direct evidence for inhibition of repair enzymes has been lacking. Using purified
Lukas Kovar et al.
Pharmaceuticals (Basel, Switzerland), 15(2) (2022-02-27)
Static in vitro permeation experiments are commonly used to gain insights into the permeation properties of drug substances but exhibit limitations due to missing physiologic cell stimuli. Thus, fluidic systems integrating stimuli, such as physicochemical fluxes, have been developed. However
Olav A Gressner et al.
Journal of hepatology, 49(5), 758-767 (2008-05-20)
Epidemiological studies suggest that coffee drinking is inversely correlated with the risk of development of liver fibrosis but the molecular basis is unknown. We investigated the pharmacological mechanisms involved in caffeine-dependent regulation of CTGF expression, an important modulator protein of
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