1,3-DIPROPYLXANTHINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N4O2
Molecular Weight	236.2703
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN1C2=C(NC=N2)C(=O)N(CCC)C1=O

InChI

InChIKey=MJVIGUCNSRXAFO-UHFFFAOYSA-N

InChI=1S/C11H16N4O2/c1-3-5-14-9-8(12-7-13-9)10(16)15(6-4-2)11(14)17/h7H,3-6H2,1-2H3,(H,12,13)

HIDE SMILES / InChI

Molecular Formula	C11H16N4O2
Molecular Weight	236.2703
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3016449 | https://www.ncbi.nlm.nih.gov/pubmed/3803571

1,3-Dipropylxanthine is an A1 and A2 adenosine receptors inhibitor. It is selective for the A1 receptors. 1,3-Dipropylxanthine was about 2- to 3-fold more potent than theophylline at A2 receptors, while being 5- to 6-fold more potent at A1 receptors.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3803571	Antagonist 2849		710.0 nM [Ki]
Adenosine A2 receptor 9 Target ID: CHEMBL2094117 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3016449	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Delineating the mode of action of adenosine A1 receptor allosteric modulators.	2010-09	20547736
N9-benzyl-substituted 1,3-dimethyl- and 1,3-dipropyl-pyrimido[2,1-f]purinediones: synthesis and structure-activity relationships at adenosine A1 and A2A receptors.	2007-07-15	17499511
Synthesis and biological activity of tricyclic aryloimidazo-, pyrimido-, and diazepinopurinediones.	2006-11-01	16844379
A1 adenosine receptors mediate hypoglycemia-induced neuronal injury.	2004-02	14765997
A1-receptor blockade: a novel approach for assessing myocardial viability in chronic ischemic cardiomyopathy.	2003-07	12835664
[3H]MRS 1754, a selective antagonist radioligand for A(2B) adenosine receptors.	2001-03-15	11266650
Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.	1999-10	10496952
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.	1995-06-09	7775460

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The Ki-values of the 1,3-Dipropylxanthine for inhibition of [3H]N6-cyclohexyladenosine ([3H]CHA) binding to rat brain membranes was 0.7 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:51:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:51:41 GMT 2025`
Record UNII	Z02T66W92D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,3-DIPROPYLXANTHINE

Systematic Name

English

1H-PURINE-2,6-DIONE, 3,9-DIHYDRO-1,3-DIPROPYL

Preferred Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIPROPYL-

Systematic Name

English

XANTHINE, 1,3-DIPROPYL-

Systematic Name

English

Code System Code Type Description

PUBCHEM

169317