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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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
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 P Rathbone et al.
Neuroreport, 2(11), 661-664 (1991-11-01)
Both extracellular guanosine and adenosine stimulated astrocyte proliferation in vitro and increased intracellular cAMP 6-fold within 2 min. The effects of both guanosine and adenosine on proliferation and cAMP levels were inhibited by antagonists of adenosine A2 receptors but augmented
W W Pawlik et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 44(2), 119-137 (1993-06-01)
Intestinal reactive hyperemia is an abrupt blood flow increase following release from anterior mesenteric arterial occlusion. We investigated the role of adenosine in reactive hyperemia. In anesthetized rats, mesenteric arterial velocity of blood flow was determined with pulsed Doppler velocimetry
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