6-Methyladenine

Base Information

• Chemical Name: 6-Methyladenine
• CAS No.: 443-72-1
• Molecular Formula: C6H7N5
• Molecular Weight: 149.155
• Hs Code.: 2933990090
• European Community (EC) Number: 207-137-7
• NSC Number: 11580
• UNII: W7IBY2BGAX
• DSSTox Substance ID: DTXSID1020857
• Nikkaji Number: J128.125I
• Wikidata: Q15632800
• Metabolomics Workbench ID: 38021
• ChEMBL ID: CHEMBL1738843
• Mol file: 443-72-1.mol

Synonyms:6-methyladenine;6-methylaminopurine;m6A;N(6)-methyladenine

Chemical Property of 6-Methyladenine

Chemical Property:

• Vapor Pressure: 0.0153mmHg at 25°C
• Melting Point: ≥300 °C
• Refractive Index: 1.792
• Boiling Point: 492.9 °C at 760 mmHg
• PKA: 9.61±0.20(Predicted)
• Flash Point: 251.9 °C
• PSA: 66.49000
• Density: 1.476 g/cm³
• LogP: 0.46760
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 149.07014524
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

N6-Methyladenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=NC=NC2=C1NC=N2
• Uses: N6-Methyladenine is a modified purine that is commonly found in genomes of prokaryotes, protists, and plants. It is less common in higher eukaryotes and extremely rare in mammals. Like methylation of other DNA residues, N6-methyladenine represents an epigenetic modification that can affect diverse DNA functions, including replication, repair, and expression. 6-(Methylamino)purine, 6-methylade is a reagent for substitution of adenine nucleotide analogs containing bicyclohexane ring system locked in northern conformation enhanced potency as py receptor antagonists. Adenine methylation as an epigenic mark has been observed in single-celled organisms and also rarely in mamalian cells.

Technology Process of 6-Methyladenine

There total 28 articles about 6-Methyladenine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methylamine (74-89-5) + 6-chloropurine hydrochloride → N-methyladenine (443-72-1)

Guidance literature:

In tetrahydrofuran; ethanol; at 120 ℃; for 2h;

DOI:10.1016/S0223-5234(02)01446-0

Reference yield: 90.0%

6-chloro-7H-purine (87-42-3,111055-92-6) + methylamine (74-89-5) → N-methyladenine (443-72-1)

Guidance literature:

In methanol; ethanol; at 120 ℃; for 4h; Sealed tube;

Reference yield: 75.0%

Benzotriazol-1-ylmethyl-(9H-purin-6-yl)-amine (111098-24-9) → N-methyladenine (443-72-1)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; for 20h; Heating;

upstream raw materials:

1-methyl-1,7⁽⁹⁾-dihydro-purine-6-thione

methylamine

6-(methylthio)-1H-purine

6H-purine-6-thione

Downstream raw materials:

methyl-nitroso-(7(9)H-purin-6-yl)-amine

N-6-methyl-2'-deoxyribofuranosil adenine

9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine

N⁶-methyladenosine

Refernces

• 1、 Cullen,Devlin. "-". . p. 1690. Retrieved 1975.
• 2、 -. "HETEROARYLPHENYLUREA DERIVATIVE". Page/Page column 138. . Retrieved 2010/11/24.
• 3、 Raboisson, Pierre,Lugnier, Claire,Muller, Christian,Reimund, Jean-Marie,Schultz, Dominique,Pinna, Guillaume,Le Bec, Alain,Basaran, Helene,Desaubry, Laurent,Gaudiot, Francois,Seloum, Mohamed,Bourguignon, Jean-Jacques. "Design, synthesis and structure-activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors". . p. 199 - 214. Retrieved 2007/10/03.