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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

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK Germany

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)
Nicolas Bousette et al.
Journal of cellular physiology, 229(3), 374-383 (2013-09-17)
Calnexin (CNX) is an endoplasmic reticulum (ER) quality control chaperone that has been implicated in ER stress. ER stress is a prominent pathological feature of various pathologic conditions, including cardiovascular diseases. However, the role of CNX and ER stress has...
Louise A Horrigan et al.
Pharmacology & therapeutics, 111(3), 877-892 (2006-03-17)
Caffeine is a member of the methylxanthine family of drugs, and is the most widely consumed behaviourally active substance in the western world. This article is focused on the impact of caffeine on immune function. In this regard, a number...
Jonathan M Hodgson et al.
The American journal of clinical nutrition, 97(5), 943-950 (2013-04-05)
Measures of blood pressure variation have been associated with cardiovascular disease and related outcomes. The regular consumption of black tea can lower blood pressure, but its effects on blood pressure variation have yet to be investigated. We aimed to assess...
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...

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