CAS 2958-98-7

2-Amino-3,9-dihydro-3-methyl-6H-purin-6-one

Description:

2-Amino-3,9-dihydro-3-methyl-6H-purin-6-one, also known as 3-methylxanthine, is a purine derivative characterized by its bicyclic structure, which includes a fused imidazole and pyrimidine ring. This compound features an amino group at the 2-position and a methyl group at the 3-position of the purine ring. It is a white to off-white crystalline solid that is soluble in water and exhibits moderate stability under standard conditions. The presence of the amino group contributes to its basicity, while the methyl group influences its biological activity. 2-Amino-3,9-dihydro-3-methyl-6H-purin-6-one is of interest in biochemistry and pharmacology, as it is related to other important compounds such as caffeine and theobromine, which are known for their stimulant effects. Its molecular structure allows it to participate in various biochemical pathways, particularly in the metabolism of nucleotides. As with many purine derivatives, it may also exhibit antioxidant properties and has potential implications in research related to cellular signaling and energy metabolism.

Formula: C₆H₇N₅O

InChI: InChI=1S/C6H7N5O/c1-11-4-3(8-2-9-4)5(12)10-6(11)7/h2H,1H3,(H,8,9)(H2,7,10,12)

InChI key: InChIKey=XHBSBNYEHDQRCP-UHFFFAOYSA-N

SMILES: CN1C2=C(C(=O)N=C1N)NC=N2

Synonyms:

• 2-Amino-3,7-dihydro-3-methyl-6H-purin-6-one
• 2-Amino-3,9-dihydro-3-methyl-6H-purin-6-one
• 2-Amino-3-methyl-6,7-dihydro-3H-purin-6-one
• 2-Amino-3-methyl-6-oxo-3,6-dihydro-7H-purine
• 2-amino-3-methyl-1,2,3,7-tetrahydro-6H-purin-6-one
• 2-amino-3-methyl-3,7-dihydro-6H-purin-6-one
• 6H-Purin-6-one, 2-amino-3,7-dihydro-3-methyl-
• 6H-Purin-6-one, 2-amino-3,7-dihydro-3-methyl- (9CI)
• 6H-Purin-6-one, 2-amino-3,9-dihydro-3-methyl-
• Guanine, 3-methyl-
• Guanine, 3-methyl- (VAN) (8CI)
• N3-Methylguanine
• N³-Methylguanine
• Nsc 62622

2-Amino-3-methyl-2,3-dihydro-1H-purin-6(7H)-one

CAS: 2958-98-7

Formula: C₆H₇N₅O

Color and Shape: Solid

Molecular weight: 165.1527

Ref: IN-DA002YTC

3-Methylguanine

Controlled Product

CAS: 2958-98-7

Applications 3-Methylguanine is a derivative of the nucleobase guanine and has been investigated as a potential purine antagonist.
References Leroy, B., et al.: J.Am. Chem. Soc., 84, 1962 (1962); Varadarajan, S., et al.: Biochem., 42, 14318 (2003); Tentori, L., et al.: J. Pharmacol. Experiment. Therap., 285, 884 (1998)

Formula: C₆H₇N₅O

Color and Shape: Neat

Molecular weight: 165.15

Ref: TR-M311810

3-Methylguanine

CAS: 2958-98-7

3-Methylguanine is an inhibitor of glycosylases, which are enzymes that remove methyl groups from the bases of DNA and RNA. 3-Methylguanine has been shown to inhibit the growth of cancer cells in a number of studies. It is also involved in the carcinogenesis of colon cancer cells by inducing DNA methylation. 3-Methylguanine inhibits the synthesis of proteins by human cells and can be used to detect proteins with high levels of methylation. The optimum pH for 3-methylguanine is neutral (pH 7). It can be found in urine samples.

Formula: C₆H₇N₅O

Purity: Min. 95%

Molecular weight: 165.15 g/mol

Ref: 3D-CAA95898