22164-16-5

Basic information

• Product Name: 2-amino-7-methyl-6-oxo-9-pentofuranosyl-6,7-dihydro-3H-purin-9-ium
• Synonyms: 2-Amino-7-methyl-6-oxo-9-pentofuranosyl-6,7-dihydro-1H-purin-9-ium; 2-Amino-9-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-7-methyl-6-oxo-6,7-dihydro-1H-purin-9-ium; 2-Amino-9-[3,4-dihydroxy-5-(hydroxyméthyl)tétrahydro-2-furanyl]-7-méthyl-6-oxo-6,7-dihydro-1H-purin-9-ium; 3H-purinium, 2-amino-6,7-dihydro-7-methyl-6-oxo-9-pentofuranosyl-
• CAS NO: 22164-16-5
• Molecular Formula: C₁₁H₁₅N₅O₅
• Molecular Weight: 298.2747
• Mol File: 22164-16-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-amino-7-methyl-6-oxo-9-pentofuranosyl-6,7-dihydro-3H-purin-9-ium(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-7-methyl-6-oxo-9-pentofuranosyl-6,7-dihydro-3H-purin-9-ium(22164-16-5)
• EPA Substance Registry System: 2-amino-7-methyl-6-oxo-9-pentofuranosyl-6,7-dihydro-3H-purin-9-ium(22164-16-5)

Safety Data

• Hazardous Substances Data: 22164-16-5(Hazardous Substances Data)

Usage

Structure

Complex chemical compound consisting of a purine base attached to a pentofuranosyl sugar through an amine group

Derivative of

Adenine

Function

Essential for various biological processes, including the synthesis of DNA and RNA

Role

Crucial in the energy transfer process in living organisms

Component of

ATP (adenosine triphosphate), an important energy carrier in cells

Therapeutic applications

Studied for potential use in the treatment of genetic disorders and cancers

Upstream product

• 684-93-5 1-methyl-1-nitrosourea 
• 118-00-3 G 
• 2181-42-2 trimethylsulphonium iodide 

Downstream Products

• 578-76-7 7-methylguanine 
• 36791-04-5 ribavirin 
• 6736-58-9 3-deazaadenosine 
• 6025-53-2 trans-zeatin 9-β-D-ribofuranoside 
• 50868-58-1 6-(2-hydroxybenzyl)adenosine 
• 110505-76-5 6-(3-hydroxybenzyl)adenosine 
• 110505-75-4 T1-11 
• 4730-45-4 8-Aza-xanthosin 
• 578-76-7 7-methylguanine 
• 58-61-7 adenosine 

Relevant articles and documents

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth—Generation by Prebiotic Methylations and Carbamoylations

The RNA-world hypothesis assumes that life on Earth started with small RNA molecules that catalyzed their own formation. Vital to this hypothesis is the need for prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here we show that isocyanates in combination with sodium nitrite establish methylating and carbamoylating reactivity compatible with early Earth conditions. These reactions lead to the formation of methylated and amino acid modified nucleosides that are still extant. Our data provide a plausible scenario for the chemical origin of certain noncanonical bases, which suggests that they are fossils of an early Earth.