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P4532

Sigma-Aldrich

(−)-N6-(2-Phenylisopropyl)adenosine

solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C19H23N5O4
Numéro CAS:
38594-96-6
Poids moléculaire :
385.42
Numéro CE :
254-028-5
Numéro MDL:
MFCD00069194
Code UNSPSC :
12352200
ID de substance PubChem :
24277681
Nomenclature NACRES :
NA.77

Forme

solid

Niveau de qualité

200

Puissance

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

Couleur

white

Solubilité

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.)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

RIRGCFBBHQEQQH-SSFGXONLSA-N

Informations sur le gène

human ... ADORA1(134)

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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8-Bromoadenosine 3′,5′-cyclic monophosphate ≥97% (HPLC)

Sigma-Aldrich

B5386

8-Bromoadenosine 3′,5′-cyclic monophosphate

Collagénase de type I The collagenase type I (from Clostridium histolyticum) is a crude collagenase preparation that can be used for the isolation of primary cells or for tissue dissociation by enzymatic means.

Sigma-Aldrich

SCR103

Collagénase de type I

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
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
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.
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
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
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