5142-23-4

Basic information

• Product Name: 3-METHYLADENINE
• Synonyms: 3H-Purin-6-amine, 3-methyl-;3-methyl-3h-purin-6-amin;3-Methyl-3H-purin-6-amine;3-methyl-adenin;Adenine, 3-methyl-;6-AMINO-3-METHYLPURINE;3-METHYLADENINE;3-methyl-3H-adenine
• CAS NO: 5142-23-4
• Molecular Formula: C₆H₇N₅
• Molecular Weight: 149.15
• EINECS: 225-908-6
• Product Categories: Amines;Bases & Related Reagents;Heterocycles;Inhibitors;Nucleotides;Akt;mTOR;PI3K
• Mol File: 5142-23-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: ~300 °C (dec.)(lit.)
• Boiling Point: 240℃
• Flash Point: 99℃
• Appearance: White/Powder
• Density: 1.60
• Vapor Pressure: 0.0387mmHg at 25°C
• Refractive Index: 1.8070 (estimate)
• Storage Temp.: Store at +4°C
• Solubility: Soluble in DMSO (up to 3 mg/ml), or in DMF (up to 10 mg/ml).
• PKA: 6.77±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20° for up to 3 months.
• BRN: 146087
• CAS DataBase Reference: 3-METHYLADENINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLADENINE(5142-23-4)
• EPA Substance Registry System: 3-METHYLADENINE(5142-23-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: AU6520000
• Hazardous Substances Data: 5142-23-4(Hazardous Substances Data)

Usage

Description

3-Methyladenine (3-MA) is a cell-permeable autophagic sequestration blocker that effectively protects cerebellar granule cells from apoptosis following serum/potassium deprivation. It is a specific inhibitor of phosphatidylinositol 3-kinase (PI3K) activity and is widely used to inhibit the initial phase of the autophagic process. 3-MA is a white powder and is also known as a multi-use inhibitor that protects cells from apoptosis.
Used in Pharmaceutical Applications:
3-Methyladenine is used as an autophagy inhibitor for blocking autophagosome formation via the inhibition of type III PI-3K. It is typically used at a concentration of 5 mM.
Used in Neuroprotection:
3-Methyladenine is used as a neuroprotective agent to protect cerebellar granule cells from apoptosis.
Used in Synthetic Chemistry:
3-Methyladenine is used as a synthetic intermediate in the chemical industry.
Used in Research and Development:
3-Methyladenine is used as a research tool to study the role of autophagy and PI3K in various cellular processes and diseases.
Used in Anticancer Applications:
Although not explicitly mentioned in the provided materials, 3-MA's role in inhibiting autophagy could potentially be explored for its use in cancer therapy, as autophagy inhibition may have implications in cancer cell survival and response to treatment.
Used in Drug Delivery Systems:
While not directly mentioned, the protective properties of 3-MA against apoptosis could be utilized in the development of drug delivery systems aimed at protecting cells from damage during the delivery of therapeutic agents.

Biochem/physiol Actions

3-Methyladenine (3-MA) is used to inhibit and study the mechanism of autophagy (lysosomal self-degradation) and apoptosis under various conditions. 3-MA inhibits autophagy by blocking autophagosome formation via the inhibition of type III phosphatidylinositol 3-kinases (PI-3K).

References

1) Seglen and Gordon?et al.?(1982),?3-Methyladenine: specific inhibitor of autophagic/lysosomal protein degradation in isolated rat hepatocytes; Proc. Natl. Acad. Sci. USA,?79?1889 2) Blommaart?et al. (1997),?The phosphatidylinositol 3-kinase inhibitors wortmannin and LY294002 inhibit autophagy in isolated rat hepatocytes; Eur. J. Biochem.,?243?240 3) McFarland?et al. (2012),?Inhibition of autophagy by 3-methyladenine protects 1321N1 astrocytoma cells against pyocyanin- and 1-hydroxyphenazine-induced toxicity; Arch. Toxicol.,?86?275 4) Zhao?et al. (2014),?Inhibition of autophagy strengthens celastrol-induced apoptosis in human pancreatic cancer in vitro and in vivo models; Curr. Mol. Med.,?14?555

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

Upstream product

• 76227-27-5 N'-benzyloxy-5-(N-methylformamido)-1H-imidazole-4-carboxamidine 
• 66224-66-6 adenine 
• 74-88-4 methyl iodide 
• 50507-48-7 N-Benzyloxy-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-formylamino-1H-imidazole-4-carboxamidine 
• 72055-61-9 5-(N-methylformamido)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine p-tuluenesulfonate 
• 72055-59-5 N'-benzyloxy-5-(N-methylformamido)-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 76227-22-0 N'-benzyloxy-1-(2-deoxy-β-D-ribofuranosyl)-5-(N-methylformamido)-1H-imidazole-4-carboxamidine 
• 76227-21-9 N'-benzyloxy-1-(2-deoxy-β-D-ribofuranosyl)-5-formamido-1H-imidazole-4-carboxamidine 
• 76227-22-0 N-Benzyloxy-5-(formyl-methyl-amino)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-imidazole-4-carboxamidine 
• 76227-21-9 N'-benzyloxy-1-(2-deoxy-β-D-ribofuranosyl)-5-formamidoimidazole-4-carboxamidine 
• 76227-24-2 1-(2-deoxy-β-D-ribofuranosyl)-5-(N-methylformamido)-1H-imidazole-4-carboxamidine p-toluenesulfonate 
• 76227-20-8 1-benzyloxy-2'-deoxyadenosine perchlorate 
• 3506-01-2 2'-Deoxyadenosine N¹-oxide 
• 155854-86-7 3-Benzyl-7-oxy-3H-purin-6-ylamine 

Downstream Products

• 1006607-26-6 C₂₆H₃₉N₅ 
• 115377-66-7 7-benzyl-3-methyl-3,7-dihydro-6H-purin-6-one 
• 185201-08-5 8-Benzyloxy-3-methyl-3H-purin-6-ylamine 
• 1006-11-7 3-methylhypoxanthine 
• 90801-87-9 4-(N-methylamino)-1H-imidazole-5-carboxamide 
• 107293-00-5 9-benzyl-3-methyladenine hydrobromide 
• 107293-01-6 7-benzyl-3-methyladenine hydrobromide 

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.

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SYNTHESIS OF ADENINE 7-OXIDE FROM ADENINE: UTILIZATION OF A BENZYL GROUP AS A CONTROL SYNTHON AT THE 3-POSITION

The first unequivocal synthetic route to adenine 7-oxide (7) has been established.The route started with peroxycarboxylic acid oxidation of 3-benzyladenine (5), readily obtainable from adenine (2) by benzylation, 8nd proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (6).