Caffeine

Sigma Reference Standard, vial of 250 mg

All Photos(1)

Synonym(s):

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

eCl@ss:

34050301

PubChem Substance ID:

24892436

NACRES:

NA.21

grade

Sigma Reference Standard

Quality Level

200

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

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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Packaging

1 vial in poly bottle

5 vials 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.