An adenosine A1 receptor antagonist
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2-chloro-N6-Cyclopentyladenosine

Item No. 36477

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-chloro-N-cyclopentyl-adenosine
CAS Number
37739-05-2
Synonyms
  • CCPA
Molecular Formula
C15H20ClN5O4
Formula Weight
369.8
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 1 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): insol
λmax
216, 275 nm
SMILES
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC3=C(NC4CCCC4)N=C(Cl)N=C32)O1
InChi Code
InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1
InChi Key
XSMYYYQVWPZWIZ-IDTAVKCVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $37

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    50 mg

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    100 mg

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    Product Description

    2-chloro-N6-Cyclopentyladenosine is an adenosine A1 receptor antagonist.1 It selectively binds to adenosine A1 over adenosine A2 receptors (Kis = 0.4 and 3,900 nM, respectively) and inhibits forskolin-induced adenylate cyclase activity in rat fat cell membranes, which endogenously express adenosine A1 receptors (IC50 = 33 nM). 2-chloro-N6-Cyclopentyladenosine (0.25 and 0.5 mg/kg) increases the electroconvulsive threshold in a mouse model of seizures induced by maximal electroshock (MES).2 It reduces infarct size in a rabbit model of coronary artery occlusion-induced myocardial infarction when administered at a dose of 0.125 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lohse, M.J., Klotz, K.N., Schwabe, U., et al. 2-Chloro-N6-cyclopentyladenosine: A highly selective agonist at A1 adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 337(6), 687-689 (1988).

    2. Łuszczki, J.J., Kozicka, M., Swiader, M.J., et al. 2-Chloro-N6-cyclopentyladenosine enhances the anticonvulsant action of carbamazepine in the mouse maximal electroshock-induced seizure model. Pharmacol. Rep. 57(6), 787-794 (2005).

    3. Tsuchida, A., Liu, G.S., Wilborn, W.H., et al. Pretreatment with the adenosine A1 selective agonist, 2-chloro-N6-cyclopentyladenosine (CCPA), causes a sustained limitation of infarct size in rabbits. Cardiovasc Res. 27(4), 652-656 (1993).