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.
Images
Key facts
- CAS number
- 147700-11-6
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 330.77 Da
- Molecular formula
- C16H15ClN4O2
- PubChem identifier
- 5353365
- Nature
- Synthetic
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
Recommended products
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.
Key facts
- CAS number
- 147700-11-6
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 330.77 Da
- Molecular formula
- C16H15ClN4O2
- PubChem identifier
- 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
Storage
- 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
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
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.
- Associated diseases and disorders
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.
Product promise
We are dedicated to supporting your work with high quality reagents and we are here for you every step of the way should you need us.
In the unlikely event of one of our products not working as expected, you are covered by our product promise.
Full details and terms and conditions can be found here:
Terms & Conditions.
1 product image
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.
Downloads
Product protocols
- Visit the general protocols
- Visit troubleshooting
Please note: All products are 'FOR RESEARCH USE ONLY. NOT FOR USE IN DIAGNOSTIC OR THERAPEUTIC PROCEDURES'.
For licensing inquiries, please contact partnerships@abcam.com