(-)-N6-Phenylisopropyl adenosine
Based on 1 Customer Validation
(-)-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.
For research use only. We do not sell to patients.
- Purity: 99.45%
- CAS No.: 38594-96-6
- Formula: C19H23N5O4
- Molecular Weight:385.42
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
All Adenosine Receptor Isoforms
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Biological Activity
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| CHO | EC50 |
1200 nM
Compound: R-(-)-PIA
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Displacement of [3H]DPCPX from human recombinant adenosine A1 receptor expressed in CHO cells
Displacement of [3H]DPCPX from human recombinant adenosine A1 receptor expressed in CHO cells
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[PMID: 16562853] |
| CHO | EC50 |
1680 nM
Compound: 1, R-PIA
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Agonist activity at human adenosine A2B receptor expressed in CHO cells assessed as stimulation of cAMP production
Agonist activity at human adenosine A2B receptor expressed in CHO cells assessed as stimulation of cAMP production
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[PMID: 17378544] |
| CHO | IC50 |
0.83 μM
Compound: R(-)-PIA
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Displacement of [3H]DPCPX from human recombinant adenosine receptor A1 expressed in CHO cells after 90 mins
Displacement of [3H]DPCPX from human recombinant adenosine receptor A1 expressed in CHO cells after 90 mins
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[PMID: 23403082] |
(-)-N6-Phenylisopropyl adenosine (0.5-8 mg/kg; s.c.) induces a dose-dependent antinociceptive effect in mice[3].
(-)-N6-Phenylisopropyl adenosine (25 μg/kg; i.p.; 15 min before the injection of Pilocarpine or saline) shows neuroprotective effects accompanied by a compensatory metabolic input in brain areas involved with seizures generation in rats[4].
(-)-N6-Phenylisopropyl adenosine (0.08-0.32 mg/kg, i.p.) exacerbates the effects of ethanol withdrawal in rats[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 38594-96-6
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Appearance Solid
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Molecular Weight 385.42
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Formula C19H23N5O4
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Color White to off-white
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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
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Synonyms
L-Phenylisopropyladenosine; L-PIA; R-PIA
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 100 mg/mL (259.46 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
H2O : 1 mg/mL (2.59 mM; ultrasonic and warming and heat to 60°C)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (277 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
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]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
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| H2O / DMSO | 1 mM | 2.5946 mL | 12.9729 mL | 25.9457 mL | 64.8643 mL |
| DMSO | 5 mM | 0.5189 mL | 2.5946 mL | 5.1891 mL | 12.9729 mL |
| 10 mM | 0.2595 mL | 1.2973 mL | 2.5946 mL | 6.4864 mL | |
| 15 mM | 0.1730 mL | 0.8649 mL | 1.7297 mL | 4.3243 mL | |
| 20 mM | 0.1297 mL | 0.6486 mL | 1.2973 mL | 3.2432 mL | |
| 25 mM | 0.1038 mL | 0.5189 mL | 1.0378 mL | 2.5946 mL | |
| 30 mM | 0.0865 mL | 0.4324 mL | 0.8649 mL | 2.1621 mL | |
| 40 mM | 0.0649 mL | 0.3243 mL | 0.6486 mL | 1.6216 mL | |
| 50 mM | 0.0519 mL | 0.2595 mL | 0.5189 mL | 1.2973 mL | |
| 60 mM | 0.0432 mL | 0.2162 mL | 0.4324 mL | 1.0811 mL | |
| 80 mM | 0.0324 mL | 0.1622 mL | 0.3243 mL | 0.8108 mL | |
| 100 mM | 0.0259 mL | 0.1297 mL | 0.2595 mL | 0.6486 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
(-)-N6-Phenylisopropyl adenosine Related Classifications
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