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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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F Saadani-Makki et al.
Neuroscience, 127(2), 505-518 (2004-07-21)
Involvement of adenosinergic A1 systems in the occurrence of respiratory perturbations encountered in newborns following an in utero caffeine exposure has been investigated on pontomedullary-spinal cord, caudal pons-medullary-spinal cord and medullary-spinal cord preparations isolated from newborn rats. According to the
María Ángeles Ruiz et al.
European journal of pharmacology, 670(2-3), 365-371 (2011-09-29)
Adenosine plays an important neuroprotective role in brain, usually mediated by the activation of adenosine A₁ receptors. Prolonged activation of a G-protein-coupled receptor generally leads to the partial loss of the responsiveness of receptor-mediated transduction pathways (desensitization). Rat immature cortical
Luigi Aurelio et al.
Journal of medicinal chemistry, 52(14), 4543-4547 (2009-06-12)
A series of 4-substituted 2-amino-3-benzoylthiophenes was screened using a functional assay of A(1)AR-mediated phosphorylation of ERK1/2 in intact CHO cells to identify both potential agonistic effects as well the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA.
Jun-Gol Song et al.
Anesthesia and analgesia, 112(6), 1494-1499 (2011-05-06)
Nerve injury can generate neuropathic pain. The accompanying mechanical allodynia may be reduced by the intrathecal administration of adenosine. The neuroprotective effects of adenosine are mediated by the adenosine triphosphate (ATP)-sensitive potassium (K(ATP)) channel. We assessed the relationship between the
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)
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