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MW 308.29 Da, Purity >98%. Potent agonist of adenosine receptors, non-selective analog of adenosine (Ki values are 14 (A1), 20 (A2A), 330 (A2B), and 6.2 nM (A3)). Offers cardio-protection by limiting infarction in situ.

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Images

Chemical Structure - NECA, adenosine agonist (AB120440), expandable thumbnail

Publications

Key facts

CAS number
35920-39-9
Purity
> 98%
Form
Solid
Molecular weight
308.29 Da
Molecular formula
C12H16N6O4
PubChem identifier
448222
Nature
Synthetic

Alternative names

Recommended products

MW 308.29 Da, Purity >98%. Potent agonist of adenosine receptors, non-selective analog of adenosine (Ki values are 14 (A1), 20 (A2A), 330 (A2B), and 6.2 nM (A3)). Offers cardio-protection by limiting infarction in situ.

Key facts

Purity
> 98%
PubChem identifier
448222
Solubility

Soluble in DMSO to 50 mM.

Biochemical name
5'-N-Ethylcarboxamidoadenosine
Biological description

Potent agonist of adenosine receptors, non-selective analog of adenosine (Ki values are 14 (A1), 20 (A2A), 330 (A2B), and 6.2 nM (A3)). Offers cardio-protection by limiting infarction in situ.

Canonical SMILES
CCNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
Isomeric SMILES
CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI
InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1
InChIKey
JADDQZYHOWSFJD-FLNNQWSLSA-N
IUPAC name
(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
Store under desiccating conditions, The product can be stored for up to 12 months

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

The adenosine receptor family includes four subtypes: Adenosine A1 Receptor Adenosine Receptor A2a Adenosine A3 Receptor (A3AR) and Adenosine A2b Receptor (ADORA2B). These receptors are G protein-coupled receptors (GPCRs) that each have distinct roles in cellular signaling. They bind adenosine a nucleoside and trigger various downstream effects. For example these receptors are integral to the regulation of myocardial oxygen consumption and cerebral blood flow. They are most commonly expressed in the central nervous system but also show presence in peripheral tissues. Each receptor subtype varies in molecular mass which can influence its interaction with ligands.

Biological function summary

These receptors modulate a wide array of physiological functions. As parts of receptor complexes they influence neurotransmission inflammation and immune responses. Specifically adenosine acts through these receptors to inhibit neurotransmitter release in the brain providing a neuroprotective effect under stress conditions. Adenosine A2a Receptor is known to play a role in vasodilation and immune cell regulation while A3AR has implications in both cardioprotection and cancer biology. These receptors function collectively and independently facilitating cellular communication and maintaining homeostasis.

Pathways

These receptors engage in important signaling cascades such as the cyclic AMP (cAMP) pathway where they either inhibit or stimulate cAMP production through different G proteins. They also participate in MAPK and PI3K/Akt pathways which are critical for cell survival and proliferation. Adenosine Receptor A2a is often studied in relation to dopamine D2 receptors highlighting its role in neuromodulation and potential therapeutic targets for neurological disorders.

Associated diseases and disorders

Dysfunction of adenosine receptors links to several conditions including cardiovascular diseases and neurological disorders. Changes in adenosine A1 Receptor activity can influence ischemic brain injury recovery while irregularities in Adenosine Receptor A2a activity are associated with chronic inflammatory diseases like asthma. Adenosine receptor activity connects to these diseases through interaction with toll-like receptors and cytokines illustrating an interplay between adenosine signaling and immune response.

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1 product image

  • Chemical Structure - NECA, adenosine agonist (ab120440), expandable thumbnail

    Chemical Structure - NECA, adenosine agonist (ab120440)

    2D chemical structure image of ab120440, NECA, adenosine agonist

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