D108
1,3-Dipropyl-7-methylxanthine
solid
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About This Item
Empirical Formula (Hill Notation):
C12H18N4O2
CAS Number:
Molecular Weight:
250.30
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
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 Code
13 - Non 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
Regulatory Information
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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
G W Sullivan et al.
Journal of immunology (Baltimore, Md. : 1950), 145(5), 1537-1544 (1990-09-01)
Human rTNF-alpha (greater than or equal to U/ml) decreased PMN nondirected and directed migration to FMLP to approximately 50% of control. Adenosine (100 microM) almost completely restored hrTNF-inhibited migration (nondirected from 54 to 92% and directed migration to from 54
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
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
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