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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
099M4096V
099M4046V
018M4119V
13171011
057M4040V

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Tamsin L Jenner et al.
Vascular pharmacology, 45(6), 341-349 (2006-07-11)
To investigate the effects of age on adenosine A1 receptor (ADORA1) mediated vascular, inotropic and chronotropic functional responses in isolated rat hearts. NECA (5'-(N-ethylcarboxamido)adenosine) and R-PIA (R-N6-(1-methyl-2-phenylethyl)adenosine) concentration-response curves were produced in Langendorff prepared hearts isolated from immature (6 weeks)
Toshihide Tabata et al.
The Journal of physiology, 581(Pt 2), 693-708 (2007-03-24)
Adenosine receptors (ARs) are G protein-coupled receptors (GPCRs) mediating the neuromodulatory actions of adenosine that influence emotional, cognitive, motor, and other functions in the central nervous system (CNS). Previous studies show complex formation between ARs and metabotropic glutamate receptors (mGluRs)
Iara Ribeiro Silva et al.
Neurobiology of disease, 41(1), 169-176 (2010-09-21)
It is well known that the uncoupling between local cerebral glucose utilization (LCGU) and local cerebral blood flow (LCBF), i.e. decrease in LCBF rates with high LCGU, is frequently associated with seizure-induced neuronal damage. This study was performed to assess
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
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