N6-Cyclopentyladenosine

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Cat.No. 1702 - N6-Cyclopentyladenosine | C15H21N5O4 | CAS No. 41552-82-3
Description: Potent, selective A1 agonist
Alternative Names: CPA
Chemical Name: N-Cyclopentyladenosine
Purity: ≥99% (HPLC)
Datasheet
Citations (12)
Reviews
Literature

Biological Activity

Potent and selective adenosine A1 receptor agonist (Ki values are 2.3, 790 and 43 nM for human A1, A2A and A3 receptors respectively; EC50 = 18600 nM for hA2B). Centrally active following systemic administration in vivo.

Technical Data

M. Wt 335.36
Formula C15H21N5O4
Storage Desiccate at +4°C
Purity ≥99% (HPLC)
CAS Number 41552-82-3
PubChem ID 657378
InChI Key SQMWSBKSHWARHU-SDBHATRESA-N
Smiles O[C@@H]1[C@@H](CO)O[C@@H](N(C=N4)C2=C4C(NC3CCCC3)=NC=N2)[C@@H]1O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
1eq. HCl 33.54 100

Preparing Stock Solutions

The following data is based on the product molecular weight 335.36. Batch specific molecular weights may vary from batch to batch due to solvent 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 2.98 mL 14.91 mL 29.82 mL
5 mM 0.6 mL 2.98 mL 5.96 mL
10 mM 0.3 mL 1.49 mL 2.98 mL
50 mM 0.06 mL 0.3 mL 0.6 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Coffin and Spealman (1987) Behavioral and cardiovascular effects of analogs of adenosine in Cynomolgus monkeys. J.Pharmacol.Exp.Ther. 241 76 PMID: 3572798

Klotz (2000) Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch.Pharmacol. 362 382 PMID: 11111832

Van der Graaf et al (1997) Mechanism-based pharmacokinetic-pharmacodynamic modeling of the effects of N6-cyclopentyladenosine analogs on heart rate in rat: estimation of in vivo operational affinity and efficacy at adenosine A1 receptors. J.Pharmacol.Exp.Ther. 283 809 PMID: 9353402


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Keywords: N6-Cyclopentyladenosine, supplier, Potent, selective, A1, agonists, Receptors, adenosines, CPA, Adenosine, A1, Receptors, Adenosine, A1, Receptors, Tocris Bioscience

12 Citations for N6-Cyclopentyladenosine

Citations are publications that use Tocris products. Selected citations for N6-Cyclopentyladenosine include:

Villalba et al (2007) Contribution of both Ca2+ entry and Ca2+ sensitization to the alpha1-adrenergic vasoconstriction of rat penile small arteries. Am J Physiol Heart Circ Physiol 292 H1157 PMID: 17085536

Jensen et al (2007) Presynaptic plasma membrane Ca2+ ATPase isoform 2a regulates excitatory synaptic transmission in rat hippocampal CA3. Neuropharmacology 579 85 PMID: 17170045

Nguyen et al (2014) Characterization of spontaneous, transient adenosine release in the caudate-putamen and prefrontal cortex. PLoS One 9 e87165 PMID: 24494035

Kavanagh et al (2015) Role of adenosine receptor subtypes in methamphetamine reward and reinforcement. PLoS One 89 265 PMID: 25301277

Pakhomov et al (2014) Cancellation of cellular responses to nanoelectroporation by reversing the stimulus polarity. Cell Mol Life Sci 71 4431 PMID: 24748074

López-Sanjurjo et al (2013) Lysosomes shape Ins(1,4,5)P3-evoked Ca2+ signals by selectively sequestering Ca2+ released from the endoplasmic reticulum. J Cell Sci 126 289 PMID: 23097044

Lemieux et al (2012) Translocation of CaMKII to dendritic microtubules supports the plasticity of local synapses. J Cell Biol 198 1055 PMID: 22965911

Bender et al (2009) Presynaptically expressed long-term potentiation increases multivesicular release at parallel fiber synapses. J Neurosci 29 10974 PMID: 19726655

Ledderose et al (2016) Adenosine arrests breast cancer cell motility by A3 receptor stimulation. Purinergic Signalling PMID: 27577957

Hobson et al (2012) Stimulation of adenosine receptors in the nucleus accumbens reverses the expression of cocaine sensitization and cross-sensitization to dopamine D2 receptors in rats. Neuropharmacology 63 1172 PMID: 22749927

Kozma et al (2013) Characterization by flow cytometry of fluorescent, selective agonist probes of the A(3) adenosine receptor. Biochem Pharmacol 85 1171 PMID: 23376019

Sousa et al (2011) Regulation of hippocampal cannabinoid CB1 receptor actions by adenosine A1 receptors and chronic caffeine administration: implications for the effects of δ9-tetrahydrocannabinol on spatial memory. Neuropsychopharmacology 36 472 PMID: 20927050


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Literature in this Area

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