Agonist of adenosine receptors
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2-chloro-3-Deazaadenosine

Item No. 9000787

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-chloro-1-β-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine
CAS Number
40656-71-1
Synonyms
  • 6-Amino-2-chloropurine riboside
  • 2-CADO
  • NSC 158900
Molecular Formula
C11H13ClN4O4
Formula Weight
300.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 2.5 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/mlEthanol: 0.25 mg/ml
λmax
274 nm
SMILES
OC[C@H]1O[C@@H](N2C(C=C(Cl)N=C3N)=C3N=C2)[C@H](O)[C@@H]1O3N=C2)C(O)C1O
InChi Code
InChI=1S/C11H13ClN4O4/c12-6-1-4-7(10(13)15-6)14-3-16(4)11-9(19)8(18)5(2-17)20-11/h1,3,5,8-9,11,17-19H,2H2,(H2,13,15)/t5-,8-,9-,11-/m1/s1
InChi Key
LIDWXUGNGGWNEU-MGUDNFKCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $85

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    5 mg

    $374

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    10 mg

    $663

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    Product Description

    2-chloro-3-Deazaadenosine is a stable analog of adenosine that acts as an agonist for adenosine receptors (Ki = 0.3, 0.08, 25.5, and 1.9 μM for A1, A2A, A2B, and A3 receptors, respectively).1,2 It can block neurotransmitter release by activating A1 receptors or inhibit neurotransmission by activating A2A receptors.3,4,5 2-chloro-3-Deazaadenosine blocks seizures by stimulating A1 receptors.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mathôt, R.A.A., Soudijn, W., Breimer, D.D., et al. Pharmacokinetic-haemodynamic relationships of 2-chloroadenosine at adenosine A1 and A2a receptors in vivo. Br. J. Pharmacol. 118(2), 369-377 (1996).

    2. Linden, J., Thai, T., Figler, H., et al. Characterization of human A2B adenosine receptors: Radioligand binding, western blotting, and coupling to Gq in human embryonic kidney 293 cells and HMC-1 mast cells. Mol. Pharmacol. 56(4), 705-713 (1999).

    3. Silinsky, E.M. On the mechanism by which adenosine receptor activation inhibits the release of acetylcholine from motor nerve endings. J. Physiol. 346, 243-256 (1984).

    4. Manzini, S., and Ballati, L. 2-Chloroadenosine induction of vagally-mediated and atropine-resistant bronchomotor responses in anaesthetized guinea-pigs. Br. J. Pharmacol. 100(2), 251-256 (1990).

    5. Pousinha, P.A., Correia, A.M., Sebastiao, A.M., et al. Predominance of adenosine excitatory over inhibitory effects on transmission at the neuromuscular junction of infant rats. J. Pharmacol. Exp. Ther. 332(1), 153-163 (2010).

    6. Malhotra, J., and Gupta, Y.K. Effect of adenosine receptor modulation on pentylenetetrazole-induced seizures in rats. Br. J. Pharmacol. 120(2), 282-288 (1997).

    7. Ates, N., Ilbay, G., and Sahin, D. Suppression of generalized seizures activity by intrathalamic 2-chloroadenosine application. Exp. Biol. Med. (Maywood) 230(7), 501-505 (2005).