X103

Sigma-Aldrich

Xanthine amine congener

≥96% (HPLC)

Empirical Formula (Hill Notation):
C21H28N6O4
CAS Number:
Molecular Weight:
428.48
MDL number:
PubChem Substance ID:

assay

≥96% (HPLC)

form

solid

color

white

solubility

DMSO: >5 mg/mL

storage temp.

room temp

SMILES string

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

InChI

1S/C21H28N6O4/c1-3-11-26-19-17(20(29)27(12-4-2)21(26)30)24-18(25-19)14-5-7-15(8-6-14)31-13-16(28)23-10-9-22/h5-8H,3-4,9-13,22H2,1-2H3,(H,23,28)(H,24,25)

Inchi Key

FIQGIOAELHTLHM-UHFFFAOYSA-N

Biochem/physiol Actions

Xanthine amine congener is a potent, nonselective adenosine receptor antagonist (A1 and A2B > A2A).

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.

Certificate of Analysis

Certificate of Origin

K N Klotz et al.
Naunyn-Schmiedeberg's archives of pharmacology, 357(1), 1-9 (1998-02-12)
Four adenosine receptor subtypes of the family of G protein-coupled receptors, designated A1, A2A, A2B and A3 are currently known. In this study all human subtypes were stably transfected into Chinese hamster ovary (CHO) cells in order to be able...
B L Sabates et al.
The Journal of surgical research, 67(2), 163-168 (1997-02-01)
The following experiments were conducted to determine whether, and the mechanisms through which, endogenous peptides alter coronary artery blood flow. Ultrasonic transit time probes were placed around the ascending aorta and left anterior descending coronary artery in groups of anesthetized...
S Takasuga et al.
The Journal of biological chemistry, 274(28), 19545-19550 (1999-07-03)
The role of adenosine receptor in regulation of insulin-induced activation of phosphoinositide 3-kinase (PI 3-kinase) and protein kinase B was studied in isolated rat adipocytes. Rat adipocytes are known to spontaneously release adenosine, which in turn binds and stimulates the...
Coral L Murrant et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 282(4), R969-R978 (2002-03-15)
To determine whether nitric oxide (NO), adenosine (Ado) receptors, or ATP-sensitive potassium (K(ATP)) channels play a role in arteriolar dilations induced by muscle contraction, we used a cremaster preparation in anesthetized hamsters in which we stimulated four to five muscle...
L T May et al.
Molecular pharmacology, 77(4), 678-686 (2010-01-21)
Allosteric binding sites on the adenosine receptor family represent potential therapeutic targets for a number of conditions involving metabolic stress. This study has identified Brilliant Black BN as a novel allosteric modulator of the adenosine A(1) and A(3) receptors. In...

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