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MW 194.19 Da, Purity >99%. Psychostimulant. Adenosine A1 and A2A receptor antagonist. Inhibits cAMP phosphodiesterases. Activates ryanodine receptor and induces intracellular calcium release.

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Images

Chemical Structure - Caffeine, Adenosine antagonist (AB120240), expandable thumbnail

Publications

Key facts

CAS number

58-08-2

Purity

> 99%

Form

Solid

Molecular weight

194.19 Da

Molecular formula

C8H10N4O2

PubChem identifier

2519

Nature

Synthetic

Alternative names

Recommended products

MW 194.19 Da, Purity >99%. Psychostimulant. Adenosine A1 and A2A receptor antagonist. Inhibits cAMP phosphodiesterases. Activates ryanodine receptor and induces intracellular calcium release.

Key facts

Purity

> 99%

PubChem identifier

2519

Solubility

Soluble in water to 100 mM.

Biochemical name

Caffeine

Biological description

Psychostimulant. Adenosine A1 and A2A receptor antagonist. Inhibits cAMP phosphodiesterases. Activates ryanodine receptor and induces intracellular calcium release.

Canonical SMILES

CN1C=NC2=C1C(=O)N(C(=O)N2C)C

InChI

InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChIKey

RYYVLZVUVIJVGH-UHFFFAOYSA-N

IUPAC name

1,3,7-trimethylpurine-2,6-dione

Storage

Shipped at conditions

Ambient - Can Ship with Ice

Appropriate short-term storage conditions

Ambient

Appropriate long-term storage conditions

Ambient

Storage information

The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.

Activity summary

Estrogen Receptor (ER) Adenosine A1 Receptor Acetylcholinesterase Gli3 Androgen Receptor PXR Estrogen Related Receptor alpha ROR gamma Adenosine A3 Receptor/A3AR and H-ERG are key proteins with varied functions and expressions throughout the body. ER also known as ESR1 weighs approximately 66 kDa and is found mainly in reproductive tissues. Adenosine A1 Receptor and Adenosine A3 Receptor are under the purinergic receptors group working with adenosine signaling while Acetylcholinesterase hydrolyzes acetylcholine at neuromuscular junctions. Gli3 part of the Gli family is a transcription factor with about 190 kDa mass active in limb development. Androgen Receptor about 110 kDa is important in male reproductive organ formation. PXR an orphan nuclear receptor regulates genes in xenobiotic metabolism. Estrogen Related Receptor alpha and ROR gamma function as nuclear hormone receptors. H-ERG with a mass of roughly 150 kDa operates as a voltage-gated potassium channel important in cardiac function.

Biological function summary

These proteins influence numerous cellular processes critical to human development and health maintenance. Estrogen and Androgen Receptors modulate various functions related to growth and reproduction. Adenosine receptors including A1 and A3 engage in cardiovascular and neural activities by affecting heart rate and neurotransmitter release operating as caffeine antagonists due to caffeine's chemical structure mimicking adenosine. Acetylcholinesterase is essential for nerve signal transmission by terminating synaptic activity through acetylcholine breakdown. Gli3 functions in patterning during embryogenesis with interactions in the Hedgehog signaling complex. PXR oversees detoxification pathways while Estrogen Related Receptor alpha and ROR gamma support metabolic regulation and immune responses respectively.

Pathways

These proteins significantly contribute to their respective biological cascades. Estrogen and Androgen Receptors participate in steroid hormone signaling influencing gene transcription. Adenosine receptors A1 and A3 play roles in purinergic signaling pathways that interact with other G protein-coupled receptors distinctly engaging caffeine in biological processes via caffeine's adenosine-like chemical formula. Acetylcholinesterase fits into the cholinergic pathway primarily affecting neuromuscular junctions and interacting with synaptic proteins. Gli3 functions prominently in the Hedgehog signaling pathway impacting developmental proteins like Sonic hedgehog. H-ERG contributes to cardiac repolarization within the cardiac action potentials pathway.

Associated diseases and disorders

These proteins serve as markers for various pathological conditions. Estrogen Receptor abnormalities are associated with breast cancer often co-expressing with proteins like HER2. Adenosine A1 and A3 Receptors linked with caffeine adenosine antagonism are studied for their roles in cardiovascular diseases working alongside proteins involved in cardiac stress responses. Acetylcholinesterase inhibitors see use in Alzheimer's disease management requiring proper synaptic chemical structure alteration for therapeutic effects. Dysfunction in Gli3 contributes to developmental disorders such as Greig cephalopolysyndactyly syndrome. H-ERG dysfunctions cause Long QT Syndrome leading to arrhythmias and cardiac complications.

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1 product image

  • Chemical Structure - Caffeine, Adenosine antagonist (ab120240), expandable thumbnail

    Chemical Structure - Caffeine, Adenosine antagonist (ab120240)

    2D chemical structure image of ab120240, Caffeine, Adenosine antagonist

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