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
• Article Data: 5

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

General Description

3-Methyl-7H-purin-6(3H)-one, also known as 3-methylxanthine, is a chemical compound belonging to the purine family. It is a derivative of caffeine and theophylline, and is commonly found in beverages like coffee and tea. It is a white, crystalline solid with a bitter taste, and is used as a drug to treat respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD). It works by relaxing the smooth muscles in the airways, making it easier to breathe. Additionally, 3-Methyl-7H-purin-6(3H)-one has stimulant effects on the central nervous system, increasing alertness and energy levels.

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 
• 118974-85-9 7-methoxy-3-methylhypoxanthine 
• 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 

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

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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.

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