35788-27-3

Basic information

• Product Name: 5'-N-METHYLCARBOXAMIDOADENOSINE
• Synonyms: 1-(6-amino-9h-purin-9-yl)-1-deoxy-n-methylribofuranuronamidehemihydrate;1-(6-amino-9h-purin-9-yl)-1-deoxy-n-methyl-ribofuranuronamidhemihydrate;MECA;MEGA;5'-N-METHYLCARBOXAMIDOADENOSINE;5'-N-methylcarboxamideadenosine
• CAS NO: 35788-27-3
• Molecular Formula: C₁₁H₁₄N₆O₄
• Molecular Weight: 294.27
• Mol File: 35788-27-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: 1.98g/cm³
• Refractive Index: 1.873
• Solubility: 0.1 M HCl: soluble
• CAS DataBase Reference: 5'-N-METHYLCARBOXAMIDOADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-N-METHYLCARBOXAMIDOADENOSINE(35788-27-3)
• EPA Substance Registry System: 5'-N-METHYLCARBOXAMIDOADENOSINE(35788-27-3)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: VJ2241000
• Hazardous Substances Data: 35788-27-3(Hazardous Substances Data)

Usage

General Description

5'-N-Methylcarboxamidoadenosine is a chemical compound that belongs to the class of purine nucleosides. It contains a modified adenine nucleobase linked to a ribose sugar and a methylcarboxamide group at the 5'-position. 5'-N-METHYLCARBOXAMIDOADENOSINE has been studied for its potential therapeutic applications, particularly in the field of cancer research, as it has shown to exhibit anti-proliferative and anti-inflammatory properties. It is also being investigated for its effects on the central nervous system, with potential applications in the treatment of neurodegenerative diseases. Additionally, 5'-N-Methylcarboxamidoadenosine has been studied for its potential use as a ligand in medicinal chemistry and drug design.

InChI:InChI=1/C11H14N6O4/c1-13-10(20)7-5(18)6(19)11(21-7)17-3-16-4-8(12)14-2-15-9(4)17/h2-3,5-7,11,18-19H,1H3,(H,13,20)(H2,12,14,15)/t5-,6+,7-,11+/m0/s1

Upstream product

• 19234-66-3 2',3'-isopropylideneadenosine-5'-carboxylic acid 
• 23754-29-2 2',3'-O-isopropylideneadenosine-5'-carboxylic acid methyl ester 
• 89177-37-7 methyl 1-[adenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate 
• 74-89-5 methylamine 
• 41110-75-2 adenosine 5'-(N-methyl)carbonyl chloride 
• 159647-45-7 (3aS,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid 4-nitro-phenyl ester 
• 39491-51-5 5'-N-methyl-2',3'-O-isopropylidenecarboxamidoadenosine 

Downstream Products

• 152918-18-8 N⁶-(3-iodobenzyl)adenosine-5'-N-methyluronamide 

Relevant articles and documents

5'-N-substituted carboxamidoadenosines as agonists for adenosine receptors

Novel as well as known 5'-N-substituted carboxamidoadenosines were prepared via new routes that provided shorter reaction times and good yields. Binding affinities were determined for rat A1 and A(2A) receptors and human A3 receptors. EC50 values were determined for cyclic AMP production in CHO cells expressing human A(2B) receptors. On all receptor subtypes relatively small substituents on the carboxamido moiety were optimal. Selectivity for the A3 receptor was found for several analogues (1a, 1d, 1h, and 1k). On A1 receptors a number of compounds, but not 5'-N-ethylcarboxamidoadenosine (NECA, 1b), showed small GTP shifts, which could be indicative of lower intrinsic activities at the A1 receptor. At the A(2B) receptor, derivatives 1i-k with modified ethyl substituents had reduced activities compared to the A(2B) reference agonist NECA (1b). Thiocarboxamido derivatives (8b and 8c) displayed considerable although decreased A(2B) receptor activity. The X-ray structure determination of compound 8b was carried out. Due to intramolecular hydrogen bonding between the carboxamido NH and the purine N3 in the crystal structure, the ribose moiety of this compound is in a syn conformation. However, theoretical calculations support that NECA (1b), and less so 8b, can readily adopt both the syn and the anti conformation, therefore not excluding the proposed anti mode of binding to the receptor.

Nucleosides and nucleotides. 200. Reinvestigation of 5′-N-ethylcarboxamidoadenosine derivatives: Structure-activity relationships for P3 purinoceptor-like proteins

The non-P1 and non-P2 muscle relaxant effect of ATP in rabbit thoracic aorta has recently been attributed to a putative P3 purinoceptor, which is activated by either adenosine or ATP. Since the physiological roles of this

Modification of the 5' Position of Purine Nucleosides. 2. Synthesis and Some Cardiovascular Properties of Adenosine-5'-(N-substituted)carboxamides

We have shown previously that the esters of adenosine-5'-carboxylic acid (10) represent a new class of potent nontoxic coronary vasodilators.For example, the ethyl ester (12), which is active by an intraduodenal or intravenous route in dogs, causes a larg