NECA

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Cat.No. 1691 - NECA | C12H16N6O4 | CAS No. 35920-39-9
Description: High affinity adenosine receptor agonist
Alternative Names: 5'-N-Ethylcarboxamidoadenosine
Chemical Name: 1-(6-Amino-9H-purin-9-yl)-1-deoxy-N-ethyl-β-D-ribofuranuronamide
Purity: ≥99% (HPLC)
Datasheet
Citations (14)
Literature

Biological Activity

High affinity adenosine receptor agonist (Ki values are 6.2, 14, and 20 nM for human A3, A1 and A2A receptors respectively; EC50 = 2.4 μM for human A2B). Inhibits platelet aggregation and is centrally active in vivo.

Compound Libraries

NECA is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 308.3
Formula C12H16N6O4
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 35920-39-9
PubChem ID 448222
InChI Key JADDQZYHOWSFJD-FLNNQWSLSA-N
Smiles O[C@@H]1[C@@H]([C@](NCC)=O)O[C@@H](N2C=NC3=C2N=CN=C3N)[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
DMSO 12.33 40

Preparing Stock Solutions

The following data is based on the product molecular weight 308.3. 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 3.24 mL 16.22 mL 32.44 mL
5 mM 0.65 mL 3.24 mL 6.49 mL
10 mM 0.32 mL 1.62 mL 3.24 mL
50 mM 0.06 mL 0.32 mL 0.65 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.

Cusack and Hourani (1981) 5'-N-ethylcarboxamidoadenosine: a potent inhibitor of human platelet aggregation. Br.J.Pharmacol. 72 443 PMID: 7260485

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

Knapp et al (2001) Adenosine agonists CGS21680 and NECA inhibit the initiation of cocaine self-administration. Pharmacol.Biochem.Behav. 68 797 PMID: 11526979


If you know of a relevant reference for NECA, please let us know.

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Keywords: NECA, supplier, adenosines, receptor, agonists, Non-Selective, Receptors, 5-N-Ethylcarboxamidoadenosine, 5'-N-Ethylcarboxamidoadenosine, Non-selective, Adenosine, Non-selective, Adenosine, Tocris Bioscience

14 Citations for NECA

Citations are publications that use Tocris products. Selected citations for NECA include:

Bulavina et al (2013) NTPDase1 activity attenuates microglial phagocytosis. Purinergic Signal 9 199 PMID: 23208703

Aggarwal et al (2013) Macrophage A2A adenosinergic receptor modulates oxygen-induced augmentation of murine lung injury. PLoS One 48 635 PMID: 23349051

Kinsey et al (2012) Autocrine adenosine signaling promotes regulatory T cell-mediated renal protection. J Am Soc Nephrol 23 1528 PMID: 22835488

Pedroza et al (2011) Interleukin-6 contributes to inflammation and remodeling in a model of adenosine mediated lung injury. J Clin Immunol 6 e22667 PMID: 21799929

Gomez et al (2011) Disparity in FcηRI-induced degranulation of primary human lung and skin mast cells exposed to adenosine. Nature 31 479 PMID: 21437670

Jin et al (2010) CD73 on tumor cells impairs antitumor T-cell responses: a novel mechanism of tumor-induced immune suppression. Cancer Res 70 2245 PMID: 20179192

Garavaglia et al (2010) Adaptation of NS cells growth and differentiation to high-throughput screening-compatible plates. BMC Neurosci 11 7 PMID: 20085655

Xi et al (2009) Adenosine A2A and A2B receptors work in concert to induce a strong protection against reperfusion injury in rat hearts. J Mol Cell Cardiol 47 684 PMID: 19695259

Clark et al (2009) Adenosine-evoked hyperpolarization of retinal ganglion cells is mediated by G-protein-coupled inwardly rectifying K+ and small conductance Ca2+-activated K+ channel activation. J Neurosci 29 11237 PMID: 19741130

Newman (2005) Calcium increases in retinal glial cells evoked by light-induced neuronal activity. Mol Neurobiol 25 5502 PMID: 15944378

Song (2017) Erythrocytes retain hypoxic adenosine response for faster acclimatization upon re-ascent. Nat Commun 8 14108 PMID: 28169986

Kim and Bynoe (2015) A2A Adenosine Receptor Regulates the Human Blood-Brain Barrier Permeability. Am J Respir Cell Mol Biol 52 664 PMID: 25262373

Poddar et al (2014) Enhanced brain distribution of modified aspartoacylase. Mol Genet Metab 113 219 PMID: 25066302

Welihinda and Amento (2014) Positive allosteric modulation of the adenosine A2a receptor attenuates inflammation. J Inflamm (Lond) 11 37 PMID: 25473378


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