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Merck
CN

27602

Caffeine

anhydrous, tested according to Ph. Eur.

Synonym(s):

Coffeinum, 1,3,7-Trimethylxanthine

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About This Item

Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
UNSPSC Code:
12352210
NACRES:
NA.21
PubChem Substance ID:
EC Number:
200-362-1
Beilstein/REAXYS Number:
17705
MDL number:
Grade:
anhydrous
Agency:
tested according to Ph. Eur.
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grade

anhydrous

Quality Segment

agency

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

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.


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pictograms

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Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

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

flash_point_f

Not applicable

flash_point_c

Not applicable



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