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P4532

Sigma-Aldrich

(−)-N6-(2-Phenylisopropyl)adenosine

solid

Synonym(s):

(R)-N6-(1-Methyl-2-phenylethyl)adenosine, N6-(L-2-Phenylisopropyl)adenosine, R-(−)-PIA

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About This Item

Empirical Formula (Hill Notation):
C19H23N5O4
CAS Number:
38594-96-6
Molecular Weight:
385.42
EC Number:
254-028-5
MDL number:
MFCD00069194
UNSPSC Code:
12352200
PubChem Substance ID:
24277681
NACRES:
NA.77

form

solid

Quality Level

200

potency

1.17 nM Ki for A1 receptors (using [3H]CHA in rat forebrain preparations)

color

white

solubility

H2O: slightly soluble 0.3 mg/mL (Solutions may be stored for several days at 4°C.)
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.6 mg/mL (Solutions may be stored for several days at 4°C.)

storage temp.

2-8°C

SMILES string

C[C@H](Cc1ccccc1)Nc2ncnc3n(cnc23)[C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O

InChI

1S/C19H23N5O4/c1-11(7-12-5-3-2-4-6-12)23-17-14-18(21-9-20-17)24(10-22-14)19-16(27)15(26)13(8-25)28-19/h2-6,9-11,13,15-16,19,25-27H,7-8H2,1H3,(H,20,21,23)/t11-,13-,15-,16-,19-/m1/s1

InChI key

RIRGCFBBHQEQQH-SSFGXONLSA-N

Gene Information

human ... ADORA1(134)

Biochem/physiol Actions

A1 adenosine receptor agonist. Affinity for adenosine receptor is approx. 100× that of the (+)-isomer.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kaori Baba et al.
Clinical and experimental pharmacology & physiology, 32(4), 263-268 (2005-04-07)
1. It is reported that alpha1-receptors and adenosine A1-receptors are involved in the ischaemic preconditioning (PC) effect on infarct size (IS). However, it is still unclear to what extent alpha1-receptors and adenosine A1-receptors contribute to the mechanism of PC. Therefore
Jong Yeon Park et al.
Journal of Korean medical science, 23(4), 678-684 (2008-08-30)
We examined the antiallodynic interaction between gabapentin and adenosine A1 receptor agonist, N(6)-(2-phenylisopropyl)-adenosine R-(-)isomer (R-PIA), in a rat model of nerve ligation injury. Rats were prepared with ligation of left L5-6 spinal nerves and intrathecal catheter implantation for drug administration.
Eduardo Paulo Morowsky Vianna et al.
Epilepsia, 46 Suppl 5, 166-173 (2005-07-01)
Adenosine is a major negative neuromodulator of synaptic activity in the central nervous system and can exert anticonvulsant and neuroprotective effects in many experimental models of epilepsy. Extracellular adenosine can be formed by a membrane-anchored enzyme ecto-5'-nucleotidase. The purposes of
H L Tan et al.
Cardiovascular drugs and therapy, 13(5), 441-447 (1999-11-05)
We tested whether the adenosine A1 receptor agonist, R-PIA, suppressed torsade de pointes (TdP) induced by the delayed rectifier potassium channel blocker clofilium. Furthermore, we studied the underlying mechanism: beta-adrenergic antagonism or ATP-sensitive K+ channel (IK-ATP) opening. In anesthetized rabbits
Kim H H Liss et al.
Journal of lipid research, 59(9), 1630-1639 (2018-06-02)
Adipocyte triglyceride storage provides a reservoir of energy that allows the organism to survive times of nutrient scarcity, but excessive adiposity has emerged as a health problem in many areas of the world. Monoacylglycerol acyltransferase (MGAT) acylates monoacylglycerol to produce
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