700-00-5

Basic information

• Product Name: 9-METHYLADENINE
• Synonyms: 1H-Purin-6-amine,9-methyl-;9H-Purin-6-amine, 9-methyl-;9-Methyl-9H-adenine;N9-Methyladenine;TIMTEC-BB SBB004081;6-AMINO-9-METHYLPURINE;9-METHYL-9H-PURIN-6-YLAMINE;9-METHYLADENINE
• CAS NO: 700-00-5
• Molecular Formula: C₆H₇N₅
• Molecular Weight: 149.15
• Product Categories: PYRIMIDINE;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Building Blocks;Heterocyclic Building Blocks;Purines;Amines;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Heterocyclic Building Blocks;M;Heterocycles
• Mol File: 700-00-5.mol

Chemical Properties

• Melting Point: 300-305 °C(lit.)
• Boiling Point: 260.22°C (rough estimate)
• Flash Point: 187.207 °C
• Appearance: Beige/Crystals
• Density: 1.1798 (rough estimate)
• Vapor Pressure: 3.67E-06mmHg at 25°C
• Refractive Index: 1.8070 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), DMSO (Slightly)
• PKA: 4.56±0.10(Predicted)
• CAS DataBase Reference: 9-METHYLADENINE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-METHYLADENINE(700-00-5)
• EPA Substance Registry System: 9-METHYLADENINE(700-00-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 700-00-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9-Methyladenine is used as an intermediate compound for the preparation of N6-benzoyl-9-methyladenine, which may have potential applications in the development of new drugs or therapies.
Used in Research and Development:
9-Methyladenine serves as a valuable compound for researchers in the field of biochemistry and molecular biology. It can be utilized in the study of adenine derivatives and their interactions with biological systems, potentially leading to the discovery of new therapeutic agents or understanding of cellular processes.
Used in Chemical Synthesis:
As a derivative of adenine, 9-Methyladenine can be used as a starting material or building block in the synthesis of more complex organic compounds, which may have various applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C6H7N5/c1-11-3-10-4-5(7)8-2-9-6(4)11/h2-3H,1H3,(H2,7,8,9)

Upstream product

• 7013-21-0 2-Chloro-9-methyladenine 
• 66224-66-6 adenine 
• 161924-07-8 2-(methoxycarbonyl)oxy-1-benzyloxy-2-benzyloxymethyl-3-butyne 
• 81619-09-2 3-pivaloyloxymethyladenine 
• 74-88-4 methyl iodide 
• 73-24-5 7H-purin-6-ylamine 
• 2346-74-9 6-chloro-9-methyl-9H-purine 

Downstream Products

• 84602-82-4 N₆-Phenyl-9-methyladenine 
• 83135-03-9 9-methyl-6-phenyl-9H-purine 
• 10184-51-7 9-methyl-1-oxy-9H-purin-6-ylamine 
• 875-31-0 9-methylhypoxanthine 
• 20427-22-9 9-methylpurine 
• 7664-41-7 ammonia 
• 56-40-6 glycine 
• 74-89-5 methylamine 
• 2009-52-1 N₆,N₉-dimethyladenine 
• 637002-23-4 cis-[(PMePh₂)2Pt(9-methyladenine)2]⁽²⁺⁾ 
• 637002-23-4 cis-[(PMePh₂)2Pt(9-methyladenine-N⁽¹⁾)(9-methyladenine-N⁽⁷⁾)]⁽²⁺⁾ 
• 880000-65-7 cis-[(PMePh₂)2Pt(N-(9-methyl-1,9-dihydro-purin-6-ylidene)-acetamidine(-1H))]NO₃ 
• 1020734-45-5 cis-[(PPh₃)2Pt(9-methyadenine(-H),N₆,N₇)][PF₆] 

Relevant articles and documents

A versatile methodology for the regioselective C8-metalation of purine bases

Purine nucleobases are excellent ligands for metal ions, forming normally coordinative Werner-type bonds by utilizing the N donor atoms of the nucleobase skeleton. Here we show that purines such as 8-chlorocaffeine and 8-bromo-9-methyladenine react with [Pt(PPh3)4] under oxidative addition of the C8-halogen bond to the metal center. The resulting PtII complexes feature a C8-bound ylidene ligand. Protonation of the ylidene at the N7/9-atom yields complexes bearing a protic N-heterocyclic carbene ligand derived from the purine base with an NMe,NH-substitution pattern.

8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands

Selective adenosine receptor modulators are potential tools for numerous therapeutic applications, including cardiovascular, inflammatory, and neurodegenerative diseases. In this work, the synthesis and biological evaluation at the four human adenosine receptor subtypes of a series of 9-substituted 8-(2-furyl)adenine derivatives are reported. Results show that 8-(2-furyl)-9-methyladenine is endowed with high affinity at the A2A subtype. Further modification of this compound with introduction of arylacetyl or arylcarbamoyl groups in N6-position takes to different effects on the A2A affinity and in particular on the selectivity versus the other three adenosine receptor subtypes. A molecular modelling analysis at three different A2A receptor crystal structures provides an interpretation of the obtained biological results.

8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radio

Electrophilic amination of adenines. Formation and characteristics of N-aminoadenines

Amination of adenine with H2N-O-SO3H in alkaline media afforded 1-, 3-, 7- and 9-aminoadenine isomers at a ratio of about 1:1:3:1. In neutral media, the product ratio of the isomers changed to about 3:1:1:0. These results were different from the regioselectivity obtained by methylation of adenine with dimethyl sulfate under similar conditions. Amination of adenine with dinitrophenoxyamine in DMF gave 1-aminoadenine as the main product and this regioselectivity was also different from that of methylation with CH3I. Chemical characteristics of these N-amino adenines are described.

Alkylation of Adenine with Functionalized tert.-Propargyl Carbonates. Synthesis of 3'-Hydroxymethyladenallene - a New Analogue of 2'-Deoxyadenosine

Esters 9d - 9g derived from acetylenic carbinol 5 were prepared and they were studied as potential alkylating agents with adenine (10), N6-benzoyl- and N6-dimethylamino-methyleneadenine (16 and 17).Carbonates 9f and 9g were the most suitable giving allene 11 and acetylene 12 (after N-deprotection in case of 16 and 17).On a scale larger than 0.2 mmol, slow addition of carbonate 9f or 9g to a solution of 10, 16 or 17 in DMF at 60 degC was most conducive to formation of allenic derivative 11.Such conditions also supperessed formation of by-products such as carbonate 13a and N9-methyladenine (14) observed in the case of methyl carbonate 9f.Intermediates 11 and 12 were deprotected using BCl3 in CH2Cl2 to give 3'-hydroxymethyladenallene (4a) and diol 15, respectively.Compound 4a was deaminated with adenosine deaminase.

METHYLATION OF ADENINE AND THERMAL TRANSFORMATIONS OF ITS N-METHYL DERIVATIVES

The methylation of adenine with methyl iodide in DMFA at 20-30 deg C gives the products from kinetically controlled reactions, i.e., 3-methyl- and 1-methyl-adeninium salts, and the reaction at 100 deg C gives 3-methyl- and 1,9-dimethyladeninium salts.The reaction mixture formed under more drastic conditions (150 deg C) consists mainly of thermodynamically stable 3,7- and 1,9-dimethyladeninium iodides.The transformation from the 1- and 3-methyladeninium iodides to the thermodynamically stable 9-methyladenine is only observed during fusion.

Anion Formation and Ring Opening of 9-Substituted Purines in Liquid Ammonia Containing Potassium Amide

Reaction of 9-methylpurine, 6-chloro-9-methylpurine, and 2',3'-O-isopropylidenenebularine with potassium amide in liquid ammonia leads to opening of the imidazole ring, yielding, after hydrolysis during the workup, 4-(substituted amino)-5-formamidopyrimidines. 6-Chloro-9-methylpurine gives, besides 6-chloro-4-(methylamino)-5-formamidopyrimidine as main product, small amounts of 9-methyladenine and 6-chloro-7,8-dihydro-8-oxo-9-methylpurine.The ring opening will involve adduct formation at position 8.Nebularine, adenosine, and 2',3'-O-isopropylideneadenosine do not react .With a greater excess of potassium amide 2',3'-O-isopropylideneadenosine loses the sugar moiety.The existence of an anion at position 8 can be proved in 9-methylpurine via scavenging with bromobenzene in liquid ammonia containing potassium amide, yielding the 8-phenyl derivative.With 6-chloro-9-(2-tetrahydropyranyl)purine this reaction gives 6-anilino-9-(2-tetrahydropyranyl)purine.Scavenging of 9-methyladenine with bromobenzene gives 6-anilino-9-methylpurine. 1H and 13C NMR spectroscopy confirm that in this strongly basic medium 7- and 9-methyladenine and 6-(methylamino)-9-methylpurine deprotonate at C-8 and lose a proton from the amino group.Both 8-(methylthio)- and 8-amino-9-methylpurine give with potassium amide in liquid ammonia opening of the imidazole ring, yielding 5-(cyanoamino)-4-(methylamino)pyrimidine, which can react further to give either 8-amino-9-methylpurine or 7,8-dihydro-8-oxo-9-methylpurine.

Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide

The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.