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D108

Sigma-Aldrich

1,3-Dipropyl-7-methylxanthine

solid

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About This Item

Empirical Formula (Hill Notation):
C12H18N4O2
CAS Number:
31542-63-9
Molecular Weight:
250.30
MDL number:
MFCD00055219
UNSPSC Code:
41106305
PubChem Substance ID:
24278401

form

solid

color

white

solubility

0.1 M NaOH: soluble
DMSO: soluble

εmax

9,500 at 273 nm

SMILES string

CCCN1C(=O)N(CCC)c2ncn(C)c2C1=O

InChI

1S/C12H18N4O2/c1-4-6-15-10-9(14(3)8-13-10)11(17)16(7-5-2)12(15)18/h8H,4-7H2,1-3H3

InChI key

QVAYTZAGDQIWMB-UHFFFAOYSA-N

Gene Information

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

Biochem/physiol Actions

Caffeine analog with some selectivity for A2 adenosine receptors.

Storage Class

13 - Non 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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J M Gidday et al.
Pediatric research, 33(6), 620-627 (1993-06-01)
The reactivity of retinal arterioles and venules to exogenous and endogenous adenosine was investigated in the newborn piglet eye in vivo. The retinal microcirculation of isoflurane-anesthetized newborn pigs was observed at 310x using videomicroscopy, and changes in the diameter of
M P Rathbone et al.
In vitro cellular & developmental biology : journal of the Tissue Culture Association, 28A(7-8), 529-536 (1992-07-01)
Presumptive astrocytes isolated from 10-day white Leghorn chick embryos, Factor VIII-positive human brain capillary endothelial cells, meningeal fibroblasts from 10-day chick embryos, Swiss mouse 3T3 cells, and human astrocytoma cell lines, SKMG-1 and U373, were rendered quiescent when placed in
Y S Lau et al.
Journal of neurochemistry, 60(2), 768-771 (1993-02-01)
The effects of the adenosine A1 agonist N6-cyclohexyladenosine (CHA) on MPTP-induced dopamine (DA) depletion in the striatum of C57BL/6 mice were studied. Twenty hours after a single injection of MPTP (30 mg/kg, s.c.), the toxin caused 62% depletion of striatal
G Evoniuk et al.
The Journal of pharmacology and experimental therapeutics, 242(3), 882-887 (1987-09-01)
Caffeine, a nonselective adenosine receptor antagonist, 7-methyl-1,3-dipropylxanthine, a purported A2 selective antagonist and a 1,3-dipropyl-8-phenylxanthine amine congener (XAC), an A1 selective antagonist, were evaluated for their in vivo selectivity at A1 vs. A2 adenosine receptors. Blockade of the negative chronotropic
M T Shamim et al.
Journal of medicinal chemistry, 32(6), 1231-1237 (1989-06-01)
The effects of 8-phenyl and 8-cycloalkyl substituents on the activity of theophylline, caffeine, 1,3-dipropylxanthine, 1,3-dipropyl-7-methylxanthine, 3-propylxanthine, and 1-propylxanthine at A1 adenosine receptors of rat brain and fat cells and at A2 adenosine receptors of rat pheochromocytoma PC12 cells and human
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