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Submit Review2-Chloro-N6-cyclopentyladenosine
Description: Potent and selective A1 agonist
Alternative Names: CCPA
Chemical Name: 2-Chloro-N-cyclopentyladenosine
Purity: ≥98% (HPLC)
Biological Activity for 2-Chloro-N6-cyclopentyladenosine
2-Chloro-N6-cyclopentyladenosine is a potent and selective adenosine A1 receptor agonist (Ki values are 0.8, 2300 and 42 nM for human A1, A2A and A3 receptors respectively; EC50 = 18800 nM for hA2B). Centrally active following systemic administration in vivo.
Compound Libraries for 2-Chloro-N6-cyclopentyladenosine
2-Chloro-N6-cyclopentyladenosine is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for 2-Chloro-N6-cyclopentyladenosine
| M. Wt | 369.81 |
| Formula | C15H20ClN5O4 |
| Storage | Desiccate at RT |
| Purity | ≥98% (HPLC) |
| CAS Number | 37739-05-2 |
| PubChem ID | 123807 |
| InChI Key | XSMYYYQVWPZWIZ-IDTAVKCVSA-N |
| Smiles | O[C@@H]1[C@@H](CO)O[C@@H](N(C=N4)C2=C4C(NC3CCCC3)=NC(Cl)=N2)[C@@H]1O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for 2-Chloro-N6-cyclopentyladenosine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 36.98 | 100 | |
| ethanol | 36.98 | 100 |
Preparing Stock Solutions for 2-Chloro-N6-cyclopentyladenosine
The following data is based on the product molecular weight 369.81. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.7 mL | 13.52 mL | 27.04 mL |
| 5 mM | 0.54 mL | 2.7 mL | 5.41 mL |
| 10 mM | 0.27 mL | 1.35 mL | 2.7 mL |
| 50 mM | 0.05 mL | 0.27 mL | 0.54 mL |
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Product Datasheets for 2-Chloro-N6-cyclopentyladenosine
References for 2-Chloro-N6-cyclopentyladenosine
References are publications that support the biological activity of the product.
Concas et al (1993) Anticonvulsant doses of 2-chloro-N6-cyclopentyladenosine, an adenosine A1 receptor agonist, reduce GABAergic transmission in different areas of the mouse brain. J.Pharmacol.Exp.Ther. 267 844 PMID: 8246158
Klotz (2000) Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch.Pharmacol. 362 382 PMID: 11111832
Lohse et al (1988) 2-Chloro-N6-cyclopentyladenosine: a highly selective agonist at A1 adenosine receptors. Naunyn Schmiedebergs Arch.Pharmacol. 337 687 PMID: 3216901
Monopoli et al (1994) Pharmacology of the highly selective A1 adenosine receptor agonist 2-chloro-N6-cyclopentyladenosine. Arzneimittelforschung 44 1305 PMID: 7848348
If you know of a relevant reference for 2-Chloro-N6-cyclopentyladenosine, please let us know.
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Keywords: 2-Chloro-N6-cyclopentyladenosine, 2-Chloro-N6-cyclopentyladenosine supplier, Potent, selective, A1, agonists, Receptors, adenosines, CCPA, Adenosine, 1705, Tocris Bioscience
11 Citations for 2-Chloro-N6-cyclopentyladenosine
Citations are publications that use Tocris products. Selected citations for 2-Chloro-N6-cyclopentyladenosine include:
Ru et al (2011) Adenosine-induced activation of esophageal nociceptors. Am J Physiol Gastrointest Liver Physiol 300 G485 PMID: 21148396
Carman et al (2011) Adenosine receptor signaling modulates permeability of the blood-brain barrier. J Neurosci 31 13272 PMID: 21917810
Fabera et al (2019) Adenosine A1 Receptor Agonist 2-chloro-N6-cyclopentyladenosine and Hippocampal Excitability During Brain Development in Rats. Front Pharmacol 10 656 PMID: 31258477
Park et al (2012) Proximal tubule sphingosine kinase-1 has a critical role in A1 adenosine receptor-mediated renal protection from ischemia. Kidney Int 82 878 PMID: 22695326
Loram et al (2013) Intrathecal injection of adenosine 2A receptor agonists reversed neuropathic allodynia through protein kinase (PK)A/PKC signaling. Brain Behav Immun 33 112 PMID: 23811314
Keene et al (2010) Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor. Biochem Pharmacol 80 188 PMID: 20346920
Long et al (2010) Adenosine receptor regulation of coronary blood flow in Ossabaw miniature swine. J Neurosci 335 781 PMID: 20855445
Crawford et al (2012) Astrocyte-derived thrombospondins mediate the development of hippocampal presynaptic plasticity in vitro. Cell Calcium 32 13100 PMID: 22993427
Hamby et al (2012) Inflammatory mediators alter the astrocyte transcriptome and calcium signaling elicited by multiple G-protein-coupled receptors. Neuroscience 32 14489 PMID: 23077035
Wu et al (2013) Opiate-induced changes in brain adenosine levels and narcotic drug responses. J Neurosci 228 235 PMID: 23098802
Goldman et al (2013) Purine receptor mediated actin cytoskeleton remodeling of human fibroblasts. BMC Pharmacol Toxicol 53 297 PMID: 23462235
Do you know of a great paper that uses 2-Chloro-N6-cyclopentyladenosine from Tocris? Please let us know.
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