1006-11-7

Basic information

• Product Name: 3-Methyl-7H-purin-6(3H)-one
• Synonyms: 3,7-Dihydro-3-methyl-6H-purin-6-one;3-Methyl-7H-purin-6(3H)-one;3-Methyl-3H- purin-6(9H)-one;3,9-Dihydro-3-methyl-6H-purin-6-one;3-Methylhypoxanthine;N3-Methylhypoxanthine;NSC 62620;6H-Purin-6-one,3,9-dihydro-3-methyl-
• CAS NO: 1006-11-7
• Molecular Formula: C₆H₆N₄O
• Molecular Weight: 150.138
• Mol File: 1006-11-7.mol

Chemical Properties

• Boiling Point: 470°Cat760mmHg
• Flash Point: 238.1°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 5.24E-09mmHg at 25°C
• Refractive Index: 1.772
• CAS DataBase Reference: 3-Methyl-7H-purin-6(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-7H-purin-6(3H)-one(1006-11-7)
• EPA Substance Registry System: 3-Methyl-7H-purin-6(3H)-one(1006-11-7)

Safety Data

• Hazardous Substances Data: 1006-11-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-7H-purin-6(3H)-one is used as a therapeutic agent for treating respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD). It functions by relaxing the smooth muscles in the airways, thereby facilitating easier breathing for patients suffering from these conditions.
Used in Beverage Industry:
As a component of coffee and tea, 3-Methyl-7H-purin-6(3H)-one contributes to the characteristic bitter taste of these beverages. Its presence in these drinks also provides a stimulant effect on the central nervous system, increasing alertness and energy levels in consumers.
Used in Research and Development:
3-Methyl-7H-purin-6(3H)-one serves as a valuable compound for scientific research, particularly in the fields of biochemistry and pharmacology. Its unique properties and interactions with biological systems make it an important subject for studying the mechanisms of action of purine-based compounds and their potential applications in medicine and other fields.

InChI:InChI=1/C6H6N4O/c1-10-3-9-6(11)4-5(10)8-2-7-4/h2-3H,1H3,(H,7,8)

Upstream product

• 28139-02-8 2‐mercapto‐3‐methylhypoxanthine 
• 89533-33-5 6-amino-5-formylamino-1-methyl-1H-pyrimidin-4-one 
• 70230-69-2 2',3',5'-tri-O-benzyl-3-methylinosine 
• 70230-74-9 3-methylinosine 
• 5142-23-4 3-methyladenine 
• 118974-81-5 hypoxanthine 7-N-oxide 
• 118974-82-6 9-(4-methoxybenzyl)hypoxanthine 7-N-oxide 
• 118974-80-4 6-<(4-methoxybenzyl)(2-oxo-2-phenylethyl)amino>-5-nitro-4(3H)-pyrimidinone 
• 70230-73-8 2',3',5'-tri-O-acetyl-3-methylinosine 
• 68768-26-3 5-(methylamino)-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 28139-02-8 3-methyl-2-thioxo-1,2,3,7⁽⁹⁾-tetrahydro-purin-6-one 
• 118974-85-9 7-methoxy-3-methylhypoxanthine 

Downstream Products

• 1006-12-8 3-Methyl-6-thiopurin 
• 115377-66-7 7-benzyl-3-methyl-3,7-dihydro-6H-purin-6-one 
• 19143-59-0 3,7-Dimethylhypoxanthin 
• 1006-12-8 3-Methyl-6-thiohypoxanthin 

Relevant articles and documents

Isolation, synthesis, and biological activity of aphrocallistin, an adenine-substituted bromotyramine metabolite from the hexactinellida sponge Aphrocallistes beatrix

A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed throug

Purines. LI. Synthesis and biological activity of hypoxanthine 7-N-oxide and related compounds

A detailed account is given of the first chemical synthesis of hypoxanthine 7-N-oxide (5), which started from coupling of 6-chloro-5-nitro-4(3H)-pyrimidinone (7) with N-(4-methoxybenzyl)phenacylamine, generated in situ from the hydrochloride (8), and proceeded through cyclization of the resulting phenacylamino pyrimidinone (9) and removal of the 4-methoxybenzyl group. The results of catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and rearrangement under acidic conditions of 5 supported the correctness of the assigned structure. An ultraviolet spectroscopic approach suggested that the neutral species of 5 exists in H2O mainly as the N(7)-OH tautomer (21). In the in vitro bioassay of antileukemic activity against murine L5178Y cells, 5 was weakly cytotoxic, with IC50 of 100 μg/ml. It did not show any antimicrobial activity even at 1000 μg/ml. None of the 9-(4-methoxybenzyl) (11) and O-methyl (12, 13, and 14) derivatives was found to be antileukemic or antimicrobial.

SYNTHESIS OF HYPOXANTHINE 7-OXIDE, A NEW N-OXIDE AT THE 6-OXOPURINE LEVEL

Hypoxanthine 7-oxide (IV) has been synthesized for the first time from 6-chloro-5-nitro-4(3H)-pyrimidinone (I) through the intermediates II and V; catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and isomerization under acidic conditions of IV supported the correctness of the assigned structure.

Purines. XXX. Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis

On treatment with boiling 1 N aqueous NaOH for 2 h, 3,7-dialkyladenine salts (7: R1, R2= Me, Et, or PhCH2; X= Br, I, or ClO4) gave 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamides (8), 1-alkyl-4-amino-1H-imidazole-5-carboxamides (11), and N6,7-dialkyladenines (14) in 33-59 percent, 2-10 percent, and 2-5 percent yields, respectively.Under slightly milder reaction conditions, 3,7-dimethyladenine hydriodide (7a: X= I) afforded 1-methyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8a) together with 3,7-dimethylhypoxanthine (2a) as a by-product; 7-benzyl-3-methyladenine hydrobromide (7c: X= Br) furnished a small amount of 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamidine (5c) besides 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8c), 1-benzyl-4-amino-1H-imidazole-5-carboxamide (11c), and 7-benzyl-N6-methyladenine (14c).These results are best interpreted in terms of pathways involving hydrolytic deamination, ring fission in the pyrimidine and imidazole moieties, cyclization, and Dimroth rearrangement.The instability of 7a (X= I) in aqueous alkali was compared with that of the four possible Nx,9-dimethyl isomers, and the relative ease with which the adenine ring underwent hydrolytic ring fission was found to decrease in the order 3,9- (17) >7,9- (18) >1,9- (19) >3,7- (7a) >>N6,9-dimethyl isomer (20).Keywords - 3,7-dialkyladenine alkaline hydrolysis; ring fission; deamination; rearrangement; 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamide; 1-alkyl-4-amino-1H-imidazole-5-carboxamide; N6,7-dialkyladenine

3-Methylinosine

3-Methylinosine (2a) has been prepared in 28 percent yield by heating 5-(methylamino)-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide (5c) with a mixture of ethyl orhtoformate and acetic anhydride, followed by ammonololysis.Compound 2a gave the stable 1,2-dihydro derivative 6 in 77 percent yield on catalytic hydrogenation over Pd-C.The pyrimidine moiety of 2a has been shown to undergo ring cleavage under alkaline conditions at a rate three times faster than that of 3,9-dimethylhypoxanthine (3a).The glycosidic bond of 2a is unusually susceptible to acidic hydrolysis and the rate was shown to be faster than that of inosine by a factor of 104.