23146-04-5

Basic information

• Product Name: 3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione
• Synonyms: 3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione;7-(3-Hydroxypropyl)theophyline;7-(3-Hydroxypropyl)theophylline
• CAS NO: 23146-04-5
• Molecular Formula: C₁₀H₁₄N₄O₃
• Molecular Weight: 238.24316
• EINECS: 245-453-7
• Mol File: 23146-04-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 508.3°Cat760mmHg
• Flash Point: 261.2°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 3.73E-11mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione(23146-04-5)
• EPA Substance Registry System: 3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione(23146-04-5)

Safety Data

• Hazardous Substances Data: 23146-04-5(Hazardous Substances Data)

Usage

General Description

3,7-dihydro-7-(3-hydroxypropyl)-1,3-dimethyl-1H-purine-2,6-dione, also known as caffeine, is a naturally occurring psychoactive compound found in coffee, tea, and certain other plant-based foods and beverages. It belongs to the class of compounds known as xanthines and is known for its stimulant effects on the central nervous system. Caffeine works by blocking the action of adenosine, a neurotransmitter that promotes relaxation and drowsiness, which leads to increased alertness and a temporary feeling of energy and focus. It is widely used as a mild stimulant and is found in many over-the-counter medications, beverages, and dietary supplements. In moderation, caffeine consumption is generally considered safe and is associated with potential health benefits such as improved cognitive function and athletic performance, but excessive intake can lead to negative side effects such as increased heart rate, jitters, and insomnia.

InChI:InChI=1/C10H14N4O3/c1-12-8-7(9(16)13(2)10(12)17)14(6-11-8)4-3-5-15/h6,15H,3-5H2,1-2H3

Upstream product

• 23146-06-7 7-(3-bromo-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 58-55-9 theophylline 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 17781-08-7 3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanoic acid 
• 23146-06-7 7-(3-bromo-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 

Relevant articles and documents

Characterization of 'mini-nucleotides' as P2X receptor agonists in rat cardiomyocyte cultures. An integrated synthetic, biochemical, and theoretical study

The design and synthesis of 'mini-nucleotides', based on a xanthine- alkyl phosphate scaffold, are described. The physiological effects of the new compounds were evaluated in rat cardiac cell culture regarding Ca2+ elevation and contractility. The results indicate biochemical and physiological profiles similar to those of ATP, although at higher concentrations. The biological target molecules of these 'mini-nucleotides' were identified by using selective P2-R and A1-R antagonists and P2-R subtype selective agonists. On the basis of these results and of experiments in Ca2+ free medium, in which [Ca2+](i) elevation was not observed, we concluded that interaction of the analogues is likely with P2X receptor subtypes, which causes Ca2+ influx. Theoretical calculations analyzing electronic effects within the series of xanthine-alkyl phosphates were performed on reduced models at quantum mechanical levels. Calculated dipole moment vectors, electrostatic potential maps, and volume parameters suggest an explanation for the activity or inactivity of the synthesized derivatives and predict a putative binding site environment for the active agonists. Xanthine-alkyl phosphate analogues proved to be selective agents for activation of P2X-R subtypes, whereas ATP activated all P2-R subtypes in cardiac cells. Therefore, these analogues may serve as prototypes of selective drugs aiming at cardiac disorders mediated through P2X receptors.