N6-Methyladenosine

Base Information

• Chemical Name: N6-Methyladenosine
• CAS No.: 1867-73-8
• Molecular Formula: C11H15N5O5
• Molecular Weight: 281.271
• Hs Code.: 2934999090
• UNII: CLE6G00625
• DSSTox Substance ID: DTXSID6020858
• Nikkaji Number: J130.669C
• Wikipedia: N6-Methyladenosine
• Wikidata: Q6951996
• Pharos Ligand ID: 3CN75SQL8RAX
• Metabolomics Workbench ID: 38443
• ChEMBL ID: CHEMBL383144
• Mol file: 1867-73-8.mol

Synonyms:6-methyladenosine;N(6)-methyladenosine;N(6)mAdo;N-methyladenosine;N6-methyladenosine;N6-methyladenosine (m6A)

Chemical Property of N6-Methyladenosine

Chemical Property:

• Vapor Pressure: 9.86E-18mmHg at 25°C
• Melting Point: 172 °C
• Refractive Index: 1.814
• Boiling Point: 649.1 °C at 760 mmHg
• PKA: 13.12±0.70(Predicted)
• Flash Point: 346.3 °C
• PSA: 125.55000
• Density: 1.85 g/cm³
• LogP: -1.44750
• Storage Temp.: −20°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.11240398
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

99% ^*data from raw suppliers

N6-Methyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O
• Isomeric SMILES: CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• Description: N6-Methyladenosine is an adenosine analog. It inhibits epinephrine-induced contraction of isolated guinea pig ileum and thoracic aorta when used at a concentration of 10 μM. N6-Methyladenosine (1 mg/kg, i.v.) decreases arterial blood pressure and renal blood flow and increases peripheral resistance in anesthetized dogs. It also inhibits tumor growth in the C3H/ST and C3HB/ST mouse models of spontaneous mammary adenocarcinomas. N6-Methyladenosine is also the most prevelant mRNA modification in eukaryotes and has roles in cell viability and development.
• Uses: N6-Methyladenosine is the most common internal modification of eukaryotic mRNA. The result of this modification is specifically recognized mRNA in the cytoplasm which regulates mRNA stability.N6-Methyladenosine is made when a protein complex containin the writer enzyme METTL3 adds a methyl group to adenosine. Two different eraser enzymes ALKBH5 and FTO can remove a methyl group to turn m6A bach into adenosine.

Technology Process of N6-Methyladenosine

There total 57 articles about N6-Methyladenosine 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: 100.0%

6-Chloropurine riboside (2004-06-0) + methylamine (74-89-5) → N6-methyladenosine (1867-73-8)

Guidance literature:

With triethylamine; In ethanol; for 4h; Reflux;

DOI:10.3389/fphar.2020.01294

Reference yield: 94.0%

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-bromo-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (74465-47-7) + methylamine (74-89-5) → N6-methyladenosine (1867-73-8)

Guidance literature:

In methanol; at 20 ℃; for 8h;

DOI:10.1021/ja029742d

Reference yield: 85.0%

N6-(N,N'-Dimethylaminomethylene)adenosine (17331-15-6) → N6-methyladenosine (1867-73-8)

Guidance literature:

With sodium tetrahydroborate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1055/s-2001-13378

upstream raw materials:

6-Chloropurine riboside

methylamine

methylamine hydrochloride

N⁶-Methoxy-N⁶-methyladenosine

Downstream raw materials:

N₆-methyl AMP

C₁₁H₁₇N₅O₁₀P₂

adenosine

C₂₅H₃₅N₇O₄S

Refernces

• 1、 Johnson et al.. "-". . p. 699,702. Retrieved 1958.
• 2、 Stein et al.. "-". . p. 2207,2210. Retrieved 1977.
• 3、 Xie, Li-Jun,Wang, Rui-Li,Wang, Dong,Liu, Li,Cheng, Liang. "Visible-light-mediated oxidative demethylation of: N 6-methyl adenines". . p. 10734 - 10737. Retrieved 2017.
• 4、 -. "SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS". . . Retrieved 2019/01/15.