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AB120442

8-(3-Chlorostyryl)caffeine, A2A receptor antagonist. MAO-B inhibitor.

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MW 330.77 Da, Purity >98%. Selective A2A receptor antagonist and MAO-B (monoamine oxidase B) inhibitor (Ki values are 54 and 100 nM, respectively). Affords strong neuroprotection against 6-OHDA-induced neurotoxicity *in vitro* and is neuroprotective in Parkinson's disease models.

View Alternative Names

A1AR, A1R, A2AAR, A2aR, AA1R_HUMAN, AA2AR_HUMAN, AA2BR_HUMAN, ADENO, ADORA 1, ADORA 2, ADORA2A, AHR_HUMAN, Adenosine A2 receptor, Adenosine A2a receptor, Adenosine receptor A1, Adenosine receptor A2a, Adenosine receptor A2b, Adenosine receptor subtype A2a, Ah receptor, Amine oxidase (flavin containing), Amine oxidase (flavin containing) A, Amine oxidase (flavin containing) B, Aromatic hydrocarbon receptor, Aryl hydrocarbon receptor, Aryl hydrocarbon receptor precursor, Class E basic helix-loop-helix protein 76, Eag-related protein 1, Ether a go go related potassium channel protein, Ether-a-go-go-related gene potassium channel 1, Ether-a-go-go-related protein 1, H-ERG, HGNC:264, HGNC:348, KCNH2_HUMAN, Kv11.1, LQT 2, MAO, MAO-A, MAO-B, Monoamine oxidase, Monoamine oxidase A, Monoamine oxidase B, Monoamine oxidase type A, Monoamine oxidase type B, Netrin 1 receptor, Potassium channel HERG, Potassium voltage gated channel subfamily H (eag related) member 2, Potassium voltage-gated channel subfamily H member 2, RDC 7, RDC 8, Ri, SQT1, Voltage gated potassium channel, subfamily H, member 2, Voltage-gated potassium channel subunit Kv11.1, adora 2b, bHLHe76, eag homolog, hA2aR, hERG-1

1 Images
Chemical Structure - 8-(3-Chlorostyryl)caffeine, A2A receptor antagonist. MAO-B inhibitor. (AB120442)
  • Chemical Structure

Lab

Chemical Structure - 8-(3-Chlorostyryl)caffeine, A2A receptor antagonist. MAO-B inhibitor. (AB120442)

2D chemical structure image of ab120442, 8-(3-Chlorostyryl)caffeine, A2A receptor antagonist. MAO-B inhibitor.

Key facts

CAS number

147700-11-6

Purity

>98%

Form

Solid

form

Molecular weight

330.77 Da

Molecular formula

C<sub>1</sub><sub>6</sub>H<sub>1</sub><sub>5</sub>ClN<sub>4</sub>O<sub>2</sub>

PubChem

5353365

Nature

Synthetic

Solubility

Soluble in DMSO to 25 mM (with heating)

Biochemical name

8-(3-Chlorostyryl)caffeine

Biological description

Selective A2A receptor antagonist and MAO-B (monoamine oxidase B) inhibitor (Ki values are 54 and 100 nM, respectively). Affords strong neuroprotection against 6-OHDA-induced neurotoxicity *in vitro* and is neuroprotective in Parkinson's disease models.

Canonical smiles

CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)C=CC3=CC(=CC=C3)Cl

Isomeric smiles

CN1C(=NC2=C1C(=O)N(C(=O)N2C)C)/C=C/C3=CC(=CC=C3)Cl

InChi

InChI=1S/C16H15ClN4O2/c1-19-12(8-7-10-5-4-6-11(17)9-10)18-14-13(19)15(22)21(3)16(23)20(14)2/h4-9H,1-3H3/b8-7+

InChiKey

WBWFIUAVMCNYPG-BQYQJAHWSA-N

IUPAC Name

8-[(E)-2-(3-chlorophenyl)ethenyl]-1,3,7-trimethylpurine-2,6-dione

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
It is important to note that this product is reported to be light sensitive|Store in the dark|Store under desiccating conditions
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Supplementary information

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

The Adenosine Receptor family includes the Adenosine A1 A2a and A2b receptors as well as the Aryl hydrocarbon Receptor and Monoamine oxidase A and B. The Adenosine A1 Receptor known for interactions with caffeine is predominantly expressed in the brain and has a molecular mass of approximately 37 kDa. The Aryl hydrocarbon Receptor involved in the body's response to environmental toxins shows wide expression across several tissues. Adenosine Receptors like A2a and A2b are found in the cardiovascular system and help regulate heart rate and coronary blood flow. Monoamine oxidases A and B present in the outer mitochondrial membrane are involved in the catabolism of neurotransmitters.
Biological function summary

These receptors and enzymes play roles in signal transduction and neurotransmitter regulation. Adenosine receptors including A2a contribute to vasodilation and anti-inflammatory effects often interacting with caffeine as an antagonist. The Aryl hydrocarbon Receptor mediates cellular responses to external stimuli while Monoamine oxidases degrade neurotransmitters affecting mood and neural activity. These proteins do not always form complexes but interact with various ligands impacting downstream effects.

Pathways

The Adenosine Receptors are integrated into the cAMP signaling pathway influencing heart rate and platelet aggregation. The Aryl hydrocarbon Receptor links to the xenobiotic metabolism pathway interacting with proteins involved in drug metabolism. Monoamine oxidases are part of the dopamine pathway and affect synaptic neurotransmitter levels interconnected with proteins like catechol-O-methyltransferase.

These biological targets connect to cardiovascular diseases and neurological disorders. Adenosine A2a Receptor antagonists show potential in treating Parkinson's disease by influencing neurotransmitter pathways similar to caffeine's action as a receptor antagonist. Monoamine oxidases relate to affective disorders with inhibitors being therapeutic for depression. Altered Aryl hydrocarbon Receptor activity links to cancer development due to its role in mediating xenobiotic metabolism and detoxification.
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Product protocols

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