104285-82-7

Basic information

• Product Name: 1-propylxanthine
• Synonyms: 1-propylxanthine
• CAS NO: 104285-82-7
• Molecular Formula: C8H10 N4 O2
• Molecular Weight: 0
• Mol File: 104285-82-7.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.367g/cm³
• Refractive Index: 1.583
• CAS DataBase Reference: 1-propylxanthine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-propylxanthine(104285-82-7)
• EPA Substance Registry System: 1-propylxanthine(104285-82-7)

Safety Data

• Hazardous Substances Data: 104285-82-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H10N4O2/c1-2-3-12-7(13)5-6(10-4-9-5)11-8(12)14/h4H,2-3H2,1H3,(H,9,10)(H,11,14)

Upstream product

• 143958-71-8 3,7-bis(4-methoxybenzyl)-3,7-dihydro-1H-purine-2,6-dione 
• 110472-90-7 6-amino-3-propyluracil 
• 142665-13-2 5,6-diamino-3-propyluracil 
• 122-51-0 orthoformic acid triethyl ester 
• 1027572-70-8 3,7-Bis-(4-methoxy-benzyl)-1-propyl-3,7-dihydro-purine-2,6-dione 
• 64-18-6 formic acid 
• 146830-67-3 6-amino-5-nitroso-3-propyluracil 
• 143958-70-7 3,7-dihydro-3-(4-methoxybenzyl)-1H-purine-2,6-dione 

Relevant articles and documents

General synthesis and properties of 1-monosubstituted xanthines

A general convenient synthesis of 1-monosubstituted xanthines (7H-imidazo[4,5-d]pyrimidine-2,6(1H,3H)-diones), starting from 3-substituted 6-aminouracils, is described. After conversion of the 6-aminouracils to the corresponding 5,6-diaminouracils, reaction with formic acid, or with triethyl orthoformate, leads to the novel xanthines in good to excellent yields, while ring closure in alkaline medium, which is commonly used in xanthine synthesis, is not successful.

Effects of Alkyl Substitutions of Xanthine Skeleton on Bronchodilation

Structure-activity relationships in a series of 1,3,7-trialkyl-xanthine were studied with guinea pigs.Relaxant actions in the tracheal muscle were increased with alkyl chain length at the 1- and 3-positions of the xanthine skeleton, but decreased by alkylation at the 7-position.Positive chronotropic actions in the right atrium were potentiated with 3-alkyl chain length but tended to decrease with 1-alkylation and diminish by 7-substitution.Consequently, while the 1- and 3-substitutions were equally important for the tracheal smooth muscle relaxation, the substitution at the 1-position was more important than the 3-substitution for bronchoselectivity.The 7-alkylation may be significant to cancel heart stimulation.There were good correlations between the smooth muscle relexant action and the cyclic AMP-PDE inhibitory activity in 3-substituents and the affinity for adenosine (A1)receptors in 1-,3-, and 7-substituents.This suggests that not only the cyclic AMP-PDE inhibitory activity but also the adenosine antagonistic activity is important in the bronchodilatory effects of alkylxanthines.Among these xanthine derivatives, 1-butyl-3-propylxanthine and its 7-methylated derivative showed high bronchoselectivity in the in vitro and in vivo experiments compared to theophylline and enprofylline and may be new candidates for bronchodilator.