7464-76-8

Usage

Physical state

Crystalline alkaloid compound

Natural sources

Tea leaves and cocoa beans

Chemical class

Xanthine alkaloids

Structural similarity

Caffeine

Primary use

Medication for respiratory conditions

Specific conditions treated

Asthma and chronic obstructive pulmonary disease (COPD)

Mechanism of action

Relaxes smooth muscles of the airways, improving breathing

Additional effects

Diuretic and cardiac stimulant properties

Other uses

Treatment of heart failure and certain types of irregular heartbeats

Side effects

Can have side effects

Drug interactions

Can interact with other medications

Safety

Should only be used under the supervision of a healthcare professional

Upstream product

• 611-59-6 paraxanthine 
• 107-08-4 1-iodo-propane 
• 16017-75-7 2-chloro-6-oxo-1,6-dihydro-1,7-dimethylpurine 
• 76194-09-7 6-amino-5-formamido-1-n-propyl-2,4-(1H,3H)-pyrimidinedione 
• 41078-02-8 3-propylxanthine 
• 16017-76-8 2-chloro-7-methyl-6-oxo-1,6-dihydropurine 
• 135462-00-9 3,7-dihydro-7-methyl-3-propyl-1H-purine-2,6-dione 
• 74-88-4 methyl iodide 
• 97184-73-1 1,7-Dimethyl-2-propoxy-1,7-dihydro-purin-6-one 

Relevant academic research and scientific papers

Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- Positions using biocatalysts

A bacterial consortium consisting of strains belonging to the genus Klebsiella and Rhodococcus quantitatively converts 1-, 3- and 7-substituted xanthines to their respective 8-oxo compounds.

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.

Analogue of Coffeine and Theophylline: Effect of Structural Alterations on Affinity at Adenosine Receptors

A variety of analogues of caffeine and theophylline in which the 1-, 3-, and 7-methyl substituents have been replaced with n-propyl, allyl, propargyl, and isobutyl and, in few cases with chloroethyl, hydroxyethyl, or benzyl were assessed for potency and s

2,6-Dialkoxy-7-methylpurines

The preparation of unsymmetrical 2,6-dialkoxy-7-methylpurines (2), and 2-alkoxy-1,7-dialkyl-6-oxo-1,6-dihydropurines (5) is described.In contrast to 1 and 2, a facile thermal lactim-lactam rearrangement from hypoxanthines 5 and 7 into xanthines 6 was observed. - Keywords: Nucleophilic heteroaromatic substitution; thermal lactim-lactam rearrangement; Sigmatropic shifts; Dialkoxy-7H-purines; Dialkyl-1H(or 3H),7H-hypoxanthines; Trialkyl-7H-xanthines