38594-96-6
Chemical Structure
(-)-N6-Phenylisopropyl adenosine
Synonym(s): L-Phenylisopropyladenosine; L-PIA; R-PIA
- CAS No.: 38594-96-6
- Formula:C19H23N5O4
- Molecular Weight:385.42
IUPAC Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(((R)-1-phenylpropan-2-yl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
InChIKey: RIRGCFBBHQEQQH-SSFGXONLSA-N
SMILES: OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(N[C@H](C)CC4=CC=CC=C4)=C3N=C2)O1
Biological Activity: (-)-N6-phenylisopropyl adenosine (L-Phenylisopropyladenosine) is a selective A1 adenosine receptor agonist. (-)-N6-phenylisopropyl adenosine inhibits K+-induced Ca2+ uptake with an IC50 value of 0.5 µM. (-)-N6-phenylisopropyl adenosine protects against ischemia-induced ventricular arrhythmias and atrial fibrillation, and exacerbates ethanol withdrawal symptoms. (-)-N6-phenylisopropyl adenosine also has analgesic effects[1][2][3][4][5][6].
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(-)-N6-Phenylisopropyl adenosine | 99.45% | (-)-N6-phenylisopropyl adenosine (L-Phenylisopropyladenosine) is a selective A1 adenosine receptor agonist. (-)-N6-phenylisopropyl adenosine inhibits K+-induced Ca2+ uptake with an IC50 value of 0.5 µM. (-)-N6-phenylisopropyl adenosine protects against ischemia-induced ventricular arrhythmias and atrial fibrillation, and exacerbates ethanol withdrawal symptoms. (-)-N6-phenylisopropyl adenosine also has analgesic effects. | ||||||||||||||||||||
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References
- [1]. Wu PH, et al. Adenosine receptor agonists inhibit K+-evoked Ca2+ uptake by rat brain cortical synaptosomes. J Neurochem. 1982 Sep;39(3):700-8. [Content Brief]
- [2]. Wainwright CL, et al. Effects of R-PIA, a selective A1 adenosine agonist, on haemodynamics and ischaemic arrhythmias in pigs. Cardiovasc Res. 1993 Jan;27(1):84-9. [Content Brief]
- [3]. Ocaña M, et al. Role of ATP-sensitive K+ channels in antinociception induced by R-PIA, an adenosine A1 receptor agonist. Naunyn Schmiedebergs Arch Pharmacol. 1994 Jul;350(1):57-62. [Content Brief]
- [4]. Silva IR, et al. The A1 receptor agonist R-Pia reduces the imbalance between cerebral glucose metabolism and blood flow during status epilepticus: could this mechanism be involved with neuroprotection? Neurobiol Dis. 2011 Jan;41(1):169-76. [Content Brief]
- [5]. Gatch MB, et al.The effects of adenosine ligands R-PIA and CPT on ethanol withdrawal. Alcohol. 1999 Aug;19(1):9-14. [Content Brief]
- [6]. Jonzon B, et al. Adenosine receptor-mediated changes in cyclic AMP production and DNA synthesis in cultured arterial smooth muscle cells. J Cell Physiol. 1985 Sep;124(3):451-6. [Content Brief]
