3881-21-8

Basic information

• Product Name: 2'-(O-METHYL)-INOSINE
• Synonyms: 2'-(O-METHYL)-INOSINE;2'-O-Methyl-D-inosine;2'-OMe-I;9-((2R,3R,4R,5R)-4-Hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-9H-purin-6-ol
• CAS NO: 3881-21-8
• Molecular Formula: C₁₁H₁₄N₄O₅
• Molecular Weight: 282.25
• Mol File: 3881-21-8.mol

Chemical Properties

• Melting Point: 153-156 °C
• Boiling Point: 669.568 °C at 760 mmHg
• Flash Point: 358.742 °C
• Appearance: White to Off-white/Powder
• Density: 1.844 g/cm³
• Storage Temp.: 2-8°C
• PKA: 8.92±0.70(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2'-(O-METHYL)-INOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-(O-METHYL)-INOSINE(3881-21-8)
• EPA Substance Registry System: 2'-(O-METHYL)-INOSINE(3881-21-8)

Safety Data

• Hazardous Substances Data: 3881-21-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
2'-(O-METHYL)-INOSINE is used as an active pharmaceutical ingredient for its hypotensive properties, helping to regulate blood pressure and potentially offering therapeutic benefits for individuals with hypertension.
Used in Research and Development:
As a component of rRNA in Crithidia fasciculata, 2'-(O-METHYL)-INOSINE is used as a research tool in molecular biology and genetics, aiding in the study of ribosomal structure and function, as well as the development of new therapeutic strategies targeting rRNA.
Used in Apoptosis Inducing Nucleosides (AINs):
2'-(O-METHYL)-INOSINE is used as a constituent of AINs, which are compounds that can induce apoptosis (programmed cell death) in certain cells. This property makes it a valuable asset in the development of treatments for various diseases, including cancer, where the induction of apoptosis can be a crucial aspect of therapy.

Upstream product

• 684-93-5 1-methyl-1-nitrosourea 
• 58-63-9 Inosine 
• 58-61-7 adenosine 
• 2140-79-6 2'-O-methyl adenosine 

Downstream Products

• 296802-65-8 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propargylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-97-5 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-96-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-allylinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532931-00-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propyl-6-thioinosine-3'-O-(2-cyanoethyl)-N,N-diisopropylphosphoramidite 
• 532930-94-2 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-allylinosine 
• 296802-64-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propargylinosine 
• 532930-99-7 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propyl-6-thioinosine 
• 532930-95-3 5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-1-propylinosine 

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.

TRINUCLEOTIDE MRNA CAP ANALOGS

What is described is a trinucleotide cap analog comprising m7G(5′)p3-N1pN2 for increased efficiency of in vitro transcription of m7G(5′)p3-RNA, wherein m7G is N7-methylguanosine or analog, (5′)p3 is a 5′,5′-triphosphate bridge, and N1 or N2 or both ribonucleotide analogs linked to each other by a phosphate, p, and wherein the trinucleotide cap analog increases the efficiency of in vitro transcription.

Antiviral amphipathic oligo- and polyribonucleotides: Analogue development and biological studies

A series of novel N1 alkylated purine nucleic acids were polymerized either enzymatically or by automated synthesis to further establish the SAR requirements for HIV, RT, and HCMV activity. Out of the series, two constructs, 2′-O-methyl-1-allylinosinic ac

Naturally occurring 2'-O-methylpurine nucleosides with hypotensive properties

2'-O-Methylinosine (1) has been isolated for the first time and shown to be an intrinsic hypotensive principle. Its probable in vivo precursor. 2'-O-methyladenosine (3), showed stronger and even orally potent hypotensive activity. Resistance of the methyladenosine (3) against adenosine deaminase is thought to contribute to its long-lasting activity. The effect of both nucleosides (1 and 3) was not accompanied with any significant change in heart rate, which is often observed with adenosine.