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27602

Sigma-Aldrich

Caffeine

anhydrous, tested according to Ph. Eur.

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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
PubChem Substance ID:
329753004
NACRES:
NA.21

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)

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1 of 4

This Item
W222402C7731W222455
Caffeine anhydrous, tested according to Ph. Eur.

Sigma-Aldrich

27602

Caffeine

Caffeine anhydrous, 99%, FCC, FG

Sigma-Aldrich

W222402

Caffeine

Caffeine meets USP testing specifications, anhydrous

Sigma-Aldrich

C7731

Caffeine

Caffeine anhydrous, natural, 99%, FCC, FG

Sigma-Aldrich

W222455

Caffeine

agency

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

agency

-

agency

USP/NF, meets USP testing specifications

agency

-

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

mp

234-236.5 °C (lit.)

form

powder

form

powder

form

crystalline, powder

form

-

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

H2O: soluble 18.7 g/L at 16 °C

solubility

-

application(s)

environmental

application(s)

flavors and fragrances

application(s)

-

application(s)

flavors and fragrances

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

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.
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.

Pictograms

Exclamation mark
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

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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
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
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
Jueng-Eun Im et al.
Pharmaceutics, 13(5) (2021-05-06)
Dermal absorption of chemicals is a key factor in risk assessment. This study investigated the effects of different amounts of application on dermal absorption and suggested an appropriate application dose for proper dermal absorption. Caffeine and testosterone were chosen as
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