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C1778

Sigma-Aldrich

Caffeine

Sigma Reference Standard, vial of 250 mg

Synonym(s):
1,3,7-Trimethylxanthine
Empirical Formula (Hill Notation):
C8H10N4O2
CAS Number:
Molecular Weight:
194.19
Beilstein:
17705
EC Number:
MDL number:
eCl@ss:
34050301
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

Sigma Reference Standard

form

crystalline
powder

packaging

vial of 250 mg

mp

234-236.5 °C (lit.)

solubility

H2O: soluble 18.7 g/L at 16 °C

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

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Packaging

5 vials in poly bottle
1 vial in poly bottle
Supplied in amber screw-cap vials

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

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

Certificate of Analysis

Certificate of Origin

CONSORT extension for reporting N-of-1 trials (CENT) 2015: Explanation and elaboration.
Larissa Shamseer et al.
BMJ (Clinical research ed.), 350, h1793-h1793 (2015-05-16)
Rohit A Sinha et al.
Hepatology (Baltimore, Md.), 59(4), 1366-1380 (2013-08-10)
Caffeine is one of the world's most consumed drugs. Recently, several studies showed that its consumption is associated with lower risk for nonalcoholic fatty liver disease (NAFLD), an obesity-related condition that recently has become the major cause of liver disease...
Markus Fehrholz et al.
American journal of physiology. Lung cellular and molecular physiology, 306(1), L101-L109 (2013-10-29)
Factors positively influencing surfactant homeostasis in general and surfactant protein B (SP-B) expression in particular are considered of clinical importance regarding an improvement of lung function in preterm infants. The objective of this study was to identify effects of physiological...
France Denoeud et al.
Science (New York, N.Y.), 345(6201), 1181-1184 (2014-09-06)
Coffee is a valuable beverage crop due to its characteristic flavor, aroma, and the stimulating effects of caffeine. We generated a high-quality draft genome of the species Coffea canephora, which displays a conserved chromosomal gene order among asterid angiosperms. Although...
Peigen Yu et al.
Food chemistry, 155, 9-16 (2014-03-07)
Thirty-nine non-volatile compounds in seven ready-to-drink (RTD) green tea samples were analysed and quantified using liquid chromatography. Taste reconstruction experiments using thirteen selected compounds were conducted to identify the key non-volatile tastants. Taste profiles of the reconstructed samples did not...

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