5461-03-0

Basic information

• Product Name: 8-aminoxanthine
• Synonyms: 8-aminoxanthine;8-AMino-1H-purine-2,6(3H,7H)-dione
• CAS NO: 5461-03-0
• Molecular Formula: C₅H₅N₅O₂
• Molecular Weight: 167.13
• Mol File: 5461-03-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.756g/cm³
• Refractive Index: 1.718
• CAS DataBase Reference: 8-aminoxanthine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-aminoxanthine(5461-03-0)
• EPA Substance Registry System: 8-aminoxanthine(5461-03-0)

Safety Data

• Hazardous Substances Data: 5461-03-0(Hazardous Substances Data)

Usage

General Description

8-aminoxanthine, also known as 8-aminoguanine, is a purine derivative that belongs to the xanthine family of compounds. It is a synthetic chemical compound that is commonly used in biochemical research as a potent inhibitor of xanthine oxidase, an enzyme involved in the metabolism of purines. 8-aminoxanthine has been shown to exhibit antioxidant and anti-inflammatory properties, making it a valuable compound in the study of oxidative stress and related physiological processes. Additionally, this chemical has been investigated for its potential therapeutic applications in the treatment of gout, hyperuricemia, and other diseases related to purine metabolism. Overall, 8-aminoxanthine is a versatile and important chemical with significant potential for biomedical and pharmaceutical research.

InChI:InChI=1/C5H5N5O2/c6-4-7-1-2(8-4)9-5(12)10-3(1)11/h(H5,6,7,8,9,10,11,12)

Upstream product

• 80106-09-8 8-nitroxanthine 

Relevant articles and documents

Analysis of peroxynitrite reactions with guanine, xanthine, and adenine nucleosides by high-pressure liquid chromatography with electrochemical detection: C8-nitration and -oxidation

Peroxynitrite, the reaction product of nitric oxide and superoxide anion, and a powerful oxidant, was found to nitrate as well as oxidize adenine, guanine, and xanthine nucleosides. A highly sensitive reverse-phase HPLC method with a dual-mode electrochemical detector, which reduces the nitro product at the first electrode and detects the reduced product by oxidation at the second electrode, was applied to detect femtomole levels of 8-nitroguanine and 8-nitroxanthine. This method was used to separate and identify the products of nitration and oxidation from the reactions of nucleosides with peroxynitrite. Peroxynitrite nitrates deoxyguanosine at neutral pH to give the very unstable 8-nitrodeoxyguanosine, in addition to 8-nitroguanine. 8-Nitrodeoxyguanosine, with a half-life of ～10 min at room temperature and ≤3 min at 37 °C, hydrolyzes at pH 7 to 8-nitroguanine. A decrease in the reaction pH resulted in a decrease in the level of C8-nitration. Peroxynitrite also oxidizes deoxyguanosine in a pH-dependent manner, to give 8-oxodeoxyguanosine with a maximum yield (0.5-0.7%) at pH 5. Guanosine and xanthosine exhibit reactivity similar to that of deoxyguanosine toward peroxynitrite at neutral pH, producing only the corresponding 8-nitronucleosides as well as 8-nitroguanine and 8-nitroxanthine, respectively. 8-Nitroguanosine at pH 7, with a half-life of several weeks at 5 °C and 5 h at 37 °C, was much more stable than 8-nitrodeoxyguanosine. C8-nitration was confirmed by dithionite reduction to the corresponding amino nucleosides, which cochromatographed with synthesized 8-amino nucleoside standards. In contrast to guanine nucleosides, adenine nucleosides undergo peroxynitrite-mediated C8 oxidation even at neutral pH to give the corresponding 8-oxoadenine nucleosides in ～0.3% yield. Adenine nitration, though minor compared to C8-oxidation, appears to occur at both C2 and C8 positions of the adenine ring. Lowering the reaction pH from 7 to 5 results in 2.4- and 2.2-fold increases in the yields of 8-oxo-dA and 8-oxo-Ado, respectively, but the level of nitration is not altered.