(-)-N6-Phenylisopropyl adenosine (Synonyms: L-Phenylisopropyladenosine; L-PIA; R-PIA)

Name: (-)-N6-Phenylisopropyl adenosine
Brand: MedChemExpress
SKU: HY-136661
Rating: 4.5 (0 reviews)

Cat. No.: HY-136661 Purity: 99.45%: Data Sheet
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(-)-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.

(-)-N6-Phenylisopropyl adenosine Chemical Structure

CAS No. : 38594-96-6

Size	Stock	Quantity
5 mg	In-stock	Estimated Time of Arrival: December 31
10 mg	In-stock	Estimated Time of Arrival: December 31
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100 mg	Get quote

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Adenosine A₁ receptor (A₁R) Adenosine A_2A receptor (A_2AR) Adenosine A_2B receptor (A_2BR) Adenosine A₃ receptor (A₃R)

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Description

Cellular Effect

Cell Line	Type	Value	Description	References
CHO	EC₅₀	1200 nM Compound: R-(-)-PIA	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	[PMID: 16562853]
CHO	EC₅₀	1680 nM Compound: 1, R-PIA	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	[PMID: 17378544]
CHO	IC₅₀	0.83 μM Compound: R(-)-PIA	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	[PMID: 23403082]

In Vitro

(-)-N6-Phenylisopropyl adenosine (1 nM-1 μM) inhibits Forskolin (HY-15371)-stimulated increase in cAMP in growth-arrested cultures of smooth muscle cells^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

(-)-N6-Phenylisopropyl adenosine (5 μg/kg; prior to coronary artery occlusion) shows a marked protection against ischaemia induced ventricular arrhythmias and fibrillation in pigs^[2].
(-)-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.

Molecular Weight

385.42

Formula

C₁₉H₂₃N₅O₄

CAS No.

38594-96-6

Appearance

Solid

Color

White to off-white

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

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

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)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.5946 mL	12.9729 mL	25.9457 mL
5 mM	0.5189 mL	2.5946 mL	5.1891 mL
10 mM	0.2595 mL	1.2973 mL	2.5946 mL

View the 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.

* 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.

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Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

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In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Calculation results:

Working solution concentration: mg/mL

Purity & Documentation

Purity: 99.45%

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Data Sheet (277 KB) SDS (252 KB)

COA (252 KB) HNMR (292 KB) LCMS (94 KB)

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

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

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

Neurological Disease Cardiovascular Disease

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(-)-N6-Phenylisopropyl adenosine38594-96-6L-Phenylisopropyladenosine L-PIA R-PIAAdenosine ReceptorP1 receptorpigs antinociceptiveneuroprotectiveethanol withdrawalratsInhibitorinhibitorinhibit

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(-)-N6-Phenylisopropyl adenosine (Synonyms: L-Phenylisopropyladenosine; L-PIA; R-PIA)

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(-)-N6-Phenylisopropyl adenosine Related Antibodies

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•Related Small Molecules:

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View All Adenosine Receptor Isoform Specific Products:

Biological Activity

Purity & Documentation

References

Customer Review

(-)-N6-Phenylisopropyl adenosine Related Antibodies

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Complete Stock Solution Preparation Table

(-)-N6-Phenylisopropyl adenosine Related Classifications

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