A selective agonist of the adenosine A2A receptor
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CGS 21680 (hydrochloride)

Item No. 17126

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]-benzenepropanoic acid, monohydrochloride
CAS Number
124431-80-7
Molecular Formula
C23H29N7O6 • HCl
Formula Weight
536.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
210, 218, 252, 292 nm
SMILES
O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=C(NCCC4=CC=C(CCC(O)=O)C=C4)N=C3N)O[C@@H]1C(NCC)=O.Cl
InChi Code
InChI=1S/C23H29N7O6.ClH/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32;/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29);1H/t16-,17+,18-,22+;/m0./s1
InChi Key
QPHVMNOEKKJYJO-MJWSIIAUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $130

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    10 mg

    $213

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    25 mg

    $412

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    Product Description

    CGS 21680 is a potent, selective agonist of the adenosine A2A receptor (Ki = 11-46 nM).1,2 It is less effective at adenosine A1 and A3 receptors (Kis = 0.5-3.1 and 0.6-1 µM, respectively) and is without effect at adenosine A2B (Ki > 10 µM).2,3,4,5 CGS 21680 is commonly used to study the actions of the adenosine A2A receptor in cells and tissues.6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ji, X.d., Gallo-Rodriguez, C., and Jacobson, K.A. A selective agonist affinity label for A3 adenosine receptors. Biochem. Biophys. Res. Commun. 203(1), 570-576 (1994).

    2. Kim, H.O., Ji, X.d., Siddiqi, S.M., et al. 2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors. J. Med. Chem. 37(21), 3614-3621 (1994).

    3. Klotz, K.-N., Hessling, J., Hegler, J., et al. Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells. Naunyn-Schmiedeberg's Arch. Pharmacol. 357(1), 1-9 (1998).

    4. 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).

    5. Varani, K., Merighi, S., Gessi, S., et al. [3H]MRE 3008F20: A novel antagonist radioligand for the pharmacological and biochemical characterization of human A3 adenosine receptors. Mol. Pharmacol. 57(5), 968-975 (2000).

    6. Cheng, M.K., Doumad, A.B., Jiang, H., et al. Epoxyeicosatrienoic acids mediate adenosine-induced vasodilation in rat prelomerular microvessels (PGMV) via A2A receptors. Br. J. Pharmacol. 141(3), 441-448 (2004).

    7. Ledent, C., Vaugeois, J.M., Schiffmann, S.N., et al. Aggressiveness, hypoalgesia and high blood pressure in mice lacking the adenosine A2A receptor. Nature 388(6643), 674-678 (1997).

    8. Gnad, T., Scheibler, S., von Kügelgen, I., et al. Adenosine activates brown adipose tissue and recruits beige adipocytes via A2A receptors. Nature 516(7531), 395-399 (2014).