443-72-1

Basic information

• Product Name: 6-(METHYLAMINO)PURINE
• Synonyms: 6-(METHYLAMINO)PURINE;N-METHYLADENINE;N6-METHYLADENINE;6-Methyladenine;6-Monomethylaminopurine;Adenine, N-methyl-;N(Sup6)-Methyladenine;N(Sup6)-Monomethyladenine
• CAS NO: 443-72-1
• Molecular Formula: C₆H₇N₅
• Molecular Weight: 149.15
• EINECS: 207-137-7
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 443-72-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: 492.9 °C at 760 mmHg
• Flash Point: 251.9 °C
• Appearance: /
• Density: 1.476 g/cm³
• Vapor Pressure: 0.0153mmHg at 25°C
• Refractive Index: 1.792
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: 6-(METHYLAMINO)PURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(METHYLAMINO)PURINE(443-72-1)
• EPA Substance Registry System: 6-(METHYLAMINO)PURINE(443-72-1)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 443-72-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 443-72-1 differently. You can refer to the following data:
1. 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.
2. 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.

Definition

ChEBI: A 6-alkylaminopurine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen.

Purification Methods

The purine is best purified by recrystallising 2g from 50mL of H2O and 1.2g of charcoal. [UV: Albert & Brown J Chem Soc 2060 1954; UV: Mason J Chem Soc 2071 1954; see also Elion et al. J Am Chem Soc 74 411 1952.] The picrate has m 265o(257o) [Bredereck et al. Chem Ber 81 307 1948]. [Beilstein 26 III/IV 3565.]

InChI:InChI=1/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-4H,1H3,(H,7,8,9,10,11)

Upstream product

• 5142-22-3 1-methyladenine 
• 111098-24-9 Benzotriazol-1-ylmethyl-(9H-purin-6-yl)-amine 
• 74-89-5 methylamine 
• 2002-35-9 N-6-methyl-2'-deoxyribofuranosil adenine 
• 593-51-1 methylamine hydrochloride 
• 87-42-3 6-chloropurine 
• 87-42-3 6-chloro-7H-purine 
• 7440-02-0 nickel 
• 66224-66-6 adenine 
• 122-51-0 orthoformic acid triethyl ester 
• 83366-44-3 5,6-diamino-4-(methylamino)pyrimidine 
• 87-42-3 6-chloro-1H-purine 
• 89073-85-8 4-amino-1,6-dihydro-6-imino-1-methyl-5-phenylazopyrimidine hydriodide 
• 89073-86-9 1,6-dihydro-6-imino-1-methyl-4-methylamino-5-phenylazopyrimidine hydriodide 

Downstream Products

• 21928-82-5 methyl-nitroso-(7(9)H-purin-6-yl)-amine 
• 70091-21-3 9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine 
• 81060-73-3 methyl-(9-benzyl-9H-purin-6-yl)amine 
• 129918-40-7 3-benzyl-6-(methylamino)purine 
• 101155-02-6 BW-A 78U 
• 142544-63-6 3'-(6-methylaminopurin-9-yl)-3'-deoxy-1',5',6'-tri-O-(methanesulfonyl)-muco-inositol 
• 32865-83-1 9-trimethylsilyl-6-methylaminopurine 
• 71118-16-6 N⁶-methyl-2',3',5'-tri-O-benzoyladenosine 
• 2009-52-1 N₆,N₉-dimethyladenine 
• 49581-45-5 methyl-(3-methyl-3H-purin-6-yl)-amine 
• 51584-35-1 N⁶,3,7-trimethyladenine 
• 49581-44-4 N⁶,1,9-trimethyladenine 
• 89204-73-9 N⁶,3-dimethyladenine hydroiodide 
• 863675-85-8 methyl-[9-(4-nitrophenyl)-9H-purin-6-yl]amine 

Relevant articles and documents

Purines. LXI. An attempted synthesis of 2'-deoxy-7-methyladenosine: Glycosidic hydrolyses of the N6-methoxy derivative and 2'-deoxy-N(x)- methyladenosines

In an attempt to synthesize 2'-deoxy-7-methyladenosine (5b), 2'-deoxy- N6-methoxyadenosine (13b) was treated with MeI in AcNMe2 at 0°C for 7h to give the 2'-deoxy-N6-methoxy-7-methyladenosine salt (14b), which was unstable and easily underwent glycosidic hydrolysis in H2O at 16-18°C to form N6-methoxy-7-methyladenine (15). On account of such instability, hydrogenolysis of 14b in H2O using hydrogen and Raney Ni catalyst failed to afford the desired nucleoside (5b). 2'-Deoxy-N6-methyladenosine (2b), 2'- deoxy-1-methyladenosine (3b), and 14b were found to undergo glycosidic hydrolysis in 0.1 N aqueous HCl at 25°C at rates of 7.92 x 10-2 min-1 (half-life 87.5 min), 5.02 x 10-3min-1 (half-life 138 min), and 2.31 x 10-2 min-1 (half-life 30.0 min), respectively, while the rate in the case of 5h was roughly estimated to be ca. 2 min-1 (half-life 0.35 min).

Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)

The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

PHOSPHODIESTERASE INHIBITORS

The present invention relates to purine derivatives, which can be used as selective phosphodiesterase (PDE) type IV inhibitors. Compounds disclosed herein can be useful in the treatment of asthma, arthritis, bronchitis, chronic obstructive pulmonary disease (COPD), psoriasis, allergic rhinitis, shock, atopic dermatitis, Crohn's disease, adult respiratory distress syndrome (ARDS), eosinophilic granuloma, allergic conjunctivitis, osteoarthritis, ulcerative colitis and other inflammatory diseases especially in humans. Also provided are processes for the preparation of disclosed compounds, pharmaceutical composition containing the disclosed compounds and their use as selective phosphodiesterase (PDE) type IV inhibitors.

Purines. LXXII. Oxidation of N6-alkyladenines with m-chloroperoxybenzoic acid leading to N6-alkyladenine 1-oxides

Oxidations of N6-methyladenine (8a) and N6-benzyladenine (8b) with m- chloroperoxybenzoic acid (mcpba) in methanol have been found to afford the N(1)-oxides 7a,b in 36% and 35% yields, respectively. The structure of 7b has been established by leading it to N6-methoxyadenine (10) through O- methylation, Dimroth rearrangement, and nonreductive debenzylation. On the other hand, N6,N6-dimethyladenine (16) afforded the N(3)-oxide 17 in 40% yield on treatment with Mcpba in methanol. On the basis of these findings, together with data accumulated for N-oxidations of adenine, N(x)- monosubstituted adenines, and 6-substituted purines, the formation of hydrogen bonding between the 6-amino Nh and the carbonyl oxygen of a peroxycarboxylic acid may account for regioselective N(1)and N(7)-oxidations of adenine and N(x)-monosubstituted adenines.