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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
Y Ren et al.
Kidney international, 59(1), 222-229 (2001-01-03)
Afferent and efferent arteriole resistance exerts critical and opposite actions in the regulation of glomerular capillary pressure (PGC) and glomerular filtration rate (GFR). Tubuloglomerular feedback (TGF) plays an important role in the regulation of afferent arteriole resistance; however, the role
C J Tseng et al.
Journal of biomedical science, 8(5), 389-394 (2001-09-11)
Adenosine was shown to inhibit norepinephrine (NE) release from sympathetic nerve endings. The purpose of this study was to examine whether endogenous adenosine restrains NE and epinephrine release from the adrenal medulla. The effects of an adenosine receptor antagonist, 1,3-dipropyl-8-(p-sulfophenyl)
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
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