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A022

Sigma-Aldrich

1,3-Dipropyl-8-(p-sulfophenyl)xanthine

powder

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About This Item

Empirical Formula (Hill Notation):
C17H20N4O5S
CAS Number:
89073-57-4
Molecular Weight:
392.43
MDL number:
MFCD00055080
UNSPSC Code:
12352202
PubChem Substance ID:
24277726
NACRES:
NA.77

form

powder

color

white

solubility

DMSO: 5 mg/mL, clear

SMILES string

CCCN1C(=O)N(CCC)c2nc([nH]c2C1=O)-c3ccc(cc3)S(O)(=O)=O

InChI

1S/C17H20N4O5S/c1-3-9-20-15-13(16(22)21(10-4-2)17(20)23)18-14(19-15)11-5-7-12(8-6-11)27(24,25)26/h5-8H,3-4,9-10H2,1-2H3,(H,18,19)(H,24,25,26)

InChI key

IWALGNIFYOBRKC-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Biochem/physiol Actions

Water soluble adenosine receptor antagonist with slight selectivity for A1 receptors.

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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Edwin K Jackson et al.
The Journal of pharmacology and experimental therapeutics, 307(3), 888-896 (2003-10-16)
Adenosine regulates tubular transport in collecting ducts (CDs); however, the sources of adenosine that modulate ion transport in CDs are unknown. The extracellular cAMP-adenosine pathway refers to the conversion of cAMP to AMP by ectophosphodiesterase, followed by metabolism of AMP
Edwin K Jackson et al.
American journal of physiology. Renal physiology, 303(7), F1000-F1005 (2012-08-10)
A(1) receptors may participate in renal sympathetic neurotransmission by enhancing the postjunctional effects of norepinephrine. The purpose of this study was to test this concept using A(1) receptor knockout (A(1)AR-/-) mice. In isolated kidneys from nontransgenic mice perfused with Tyrode's
Edwin K Jackson et al.
The Journal of pharmacology and experimental therapeutics, 320(1), 117-123 (2006-10-10)
The extracellular cAMP-adenosine pathway is the cellular egress of cAMP followed by extracellular conversion of cAMP to adenosine by the sequential actions of ecto-phosphodiesterase and ecto-5'-nucleotidase. Although detailed studies in isolated organs, tissues, and cells provide evidence for an extracellular
J W Daly et al.
Journal of medicinal chemistry, 28(4), 487-492 (1985-04-01)
A series of 8-(substituted phenyl) derivatives of theophylline and other 1,3-dialkylxanthines were evaluated for potency and selectivity as antagonists at A1- and A2-adenosine receptors in brain tissue. Theophylline has a similar potency (Ki = 14 microM) at both A1 and
S P Tofovic et al.
Shock (Augusta, Ga.), 16(3), 196-202 (2001-09-04)
The purpose of this study was to investigate in vivo the effects of modulating the adenosine system on endotoxin-induced release of cytokines and changes in heart performance and neurohumoral status in early, profound endotoxemia in rats. Time/pressure variables of heart
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