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P101

Sigma-Aldrich

2-Phenylaminoadenosine

>97%, solid

Synonym(s):

CV-1808

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About This Item

Empirical Formula (Hill Notation):
C16H18N6O4
CAS Number:
53296-10-9
Molecular Weight:
358.35
MDL number:
MFCD00055119
UNSPSC Code:
12352200
PubChem Substance ID:
24277727
NACRES:
NA.77

Quality Level

100

assay

>97%

form

solid

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 3.6 mg/mL
H2O: insoluble
absolute ethanol: slightly soluble
ethanol: water (1:1): soluble
methanol: soluble (hot)

storage temp.

−20°C

SMILES string

Nc1nc(Nc2ccccc2)nc3n(cnc13)[C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O

InChI

1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)/t9-,11-,12-,15-/m1/s1

InChI key

SCNILGOVBBRMBK-SDBHATRESA-N

Gene Information

human ... ADORA2A(135) , ADORA2B(136)
rat ... Adora1(29290) , Adora2a(25369)

Biochem/physiol Actions

Selective A2 adenosine receptor agonist; potent coronary vasodilator; weak inhibitor of adenosine uptake by rat cerebral cortical synaptosomes.

Reconstitution

Solutions should be freshly prepared.

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)

Certificates of Analysis (COA)

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D A Taylor et al.
European journal of pharmacology, 85(3-4), 335-338 (1982-12-03)
2-Chloroadenosine (2-CADO) and 2-phenylaminoadenosine (CV 1808) were compared in a CNS purinergic receptor binding assay and the inhibition of neurogenic contractions of the vas deferens. Both 2-CADO and CV 1808 are more potent than adenosine in both preparations. CV 1808
J W Phillis et al.
Pharmacology, biochemistry, and behavior, 24(2), 263-270 (1986-02-01)
Mice were implanted with chronic indwelling cannulae in the lateral cerebral ventricle. A series of adenosine analogs and related compounds were injected into the lateral ventricle (ICVT) and their effects on spontaneous locomotor activity recorded. All analogs produced dose-related decreases
P H Wu et al.
General pharmacology, 15(3), 251-254 (1984-01-01)
Various adenosine derivatives, methylxanthines and other compounds were tested for their abilities to inhibit the rapid uptake of adenosine by rat cerebral cortical synaptosomes. Several pharmacologically potent derivatives of adenosine were weak inhibitors of uptake with IC20 values in excess
Stimulation of Adenosine A
Sarawuth Phosri et al.
Frontiers in pharmacology, 8, 428-428 (2017-07-18)
Mark Soave et al.
SLAS discovery : advancing life sciences R & D, 25(2), 186-194 (2019-10-05)
Receptor internalization in response to prolonged agonist treatment is an important regulator of G protein-coupled receptor (GPCR) function. The adenosine A1 receptor (A1AR) is one of the adenosine receptor family of GPCRs, and evidence for its agonist-induced internalization is equivocal.

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