1681-10-3

Basic information

• Product Name: 6-methyl-1H-purin-2-amine
• Synonyms: 6-methyl-1H-purin-2-amine;1H-Purin-2-amine, 6-methyl- (9CI);6-Methyl-9H-purin-2-amine
• CAS NO: 1681-10-3
• Molecular Formula: C₆H₇N₅
• Molecular Weight: 149.15328
• EINECS: 216-857-0
• Product Categories: PYRIMIDINE
• Mol File: 1681-10-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 251 °C
• Boiling Point: 291.8°Cat760mmHg
• Flash Point: 130.3°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 2.99E-13mmHg at 25°C
• Refractive Index: 1.776
• PKA: 8.49±0.20(Predicted)
• CAS DataBase Reference: 6-methyl-1H-purin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-1H-purin-2-amine(1681-10-3)
• EPA Substance Registry System: 6-methyl-1H-purin-2-amine(1681-10-3)

Safety Data

• Hazardous Substances Data: 1681-10-3(Hazardous Substances Data)

Usage

Description

6-methyl-1H-purin-2-amine, also known as 6-Methyladenine, is a purine derivative chemical compound derived from the adenine molecule, which is a fundamental component of DNA and RNA. It is found in a diverse range of organisms, including plants, animals, and microorganisms. 6-methyl-1H-purin-2-amine is recognized for its significant biological activities, such as being a precursor in the biosynthesis of caffeine and serving as a substrate for various enzymes. Moreover, it holds potential in pharmaceutical applications, particularly in the development of treatments for neurological disorders and cancer. Its role in regulating cellular processes and gene expression underscores its importance in understanding the molecular mechanisms of life.

Uses

Used in Pharmaceutical Industry:
6-methyl-1H-purin-2-amine is used as a precursor in the biosynthesis of caffeine, which is utilized for its stimulating effects in various pharmaceutical formulations and beverages.
Used in Neurological Disorders Research and Treatment:
6-methyl-1H-purin-2-amine is used as a research compound for understanding the molecular mechanisms underlying neurological disorders, potentially leading to the development of new therapeutic agents.
Used in Cancer Treatment:
6-methyl-1H-purin-2-amine is used as a potential pharmaceutical agent in cancer treatment, given its role in cellular processes and gene expression, which may contribute to the development of targeted therapies.
Used in Enzyme Research and Development:
6-methyl-1H-purin-2-amine is used as a substrate in the study and development of enzymes, which can aid in the advancement of biocatalysts and other biotechnological applications.
Used in Molecular Biology:
6-methyl-1H-purin-2-amine is used in molecular biology for its role in gene expression and regulation, which is crucial for understanding and manipulating genetic information in various organisms.

InChI:InChI=1/C6H7N5/c1-3-4-5(9-2-8-4)11-6(7)10-3/h2H,1H3,(H3,7,8,9,10,11)

Upstream product

• 60914-71-8 6-methyl-2,4,5-triaminopyrimidine 
• 77287-34-4 formamide 
• 228874-35-9 9-benzyl-6-methyl-9H-purin-2-ylamine 
• 753503-84-3 N-(2,4-diamino-6-methyl-pyrimidin-5-yl)-formamide 

Relevant articles and documents

Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base

A series of dialkyl esters of purine and pyrimidine N-[2- (phosphonomethoxy)ethyl] derivatives substituted at position 2, 6, or 8 of the purine base or position 2, 4, or 5 of the pyrimidine base were prepared by alkylation of the appropriate heterocyclic base with 2- chloroethoxymethylphosphonate diester in the presence of sodium hydride, cesium carbonate, or 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) in dimethylformamide. Additional derivatives were obtained by the transformations of the bases in the suitably modified intermediates bearing reactive functions at the base moiety. The diesters were converted to the corresponding monoesters by sodium azide treatment, while the free acids were obtained from the diester by successive treatment with bromotrimethylsilane and hydrolysis. None of the PME derivatives in the pyrimidine series, their 6-aza or 3-deaza analogues, exhibited any activity against DNA viruses or retroviruses tested, except for the 5-bromocytosine derivative. Substitution of the adenine ring in PMEA at position 2 by Cl, F, or OH group decreased the activity against all DNA viruses tested. PMEDAP was highly active against HSV-1, HSV-2, and VZV in the concentration range (EC50) of 0.07-2 μg/mL. Also the 2-amino-6-chloropurine derivative was strongly active (EC50 = 0.1- 0.4 μg/mL) against herpes simplex viruses and (EC50 = 0.006-0.3 μg/mL) against CMV and VZV. PMEG was the most active compound of the whole series against DNA viruses (EC50 ~0.01-0.02 μg/mL), though it exhibited significant toxicity against the host cells. The base-modified compounds did not show any appreciable activity against DNA viruses except for 7-deazaPMEA (IC50 ~7.5 μg/mL) against HIV-1 and MSV. The neutral (diisopropyl, diisooctyl) diesters of PMEA were active against CMV and VZV, while the corresponding monoesters were inactive. The diisopropyl ester of the 2- chloroadenine analogue of PMEA showed substantially (10-100x) higher activity against CMV and VZV than the parent phosphonate. Also, the diisopropyl and diisooctyl ester of PMEDAP inhibited CMV and VZV, but esterification of the phosphonate residue did not improve the activity against either MSV or HIV.