3-Methyladenine

• CAS: 5142-23-4
• Catalog Number: ACM5142234-1
• Category: Inhibitors
• Molecular Weight: 149.15
• Molecular Formula: C6H7N5
• Description: 3-Methyladenine (3-MA) is a PI3K inhibitor. 3-Methyladenine is a widely used inhibitor of autophagy via its inhibitory effect on class III PI3K.
• Synonyms: 3-Methylpurin-6-amine
• IUPAC Name: 3-Methyl-7h-purin-6-imine
• SMILES: CN1C=NC(=N)C2=C1N=CN2
• InChI: InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3,7H,1H3,(H,8,9)
• InChI Key: ZPBYVFQJHWLTFB-UHFFFAOYSA-N
• Boiling Point: 240 °C
• Melting Point: 300 °C(lit.)
• Flash Point: 99 °C
• Density: 1.60 g/cm³
• Appearance: White powder
• Storage: Keep in dark place, sealed in dry, room temperature
• Complexity: 211
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 149.07014524
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 2
• Monoisotopic Mass: 149.07014524
• Physical State: Powder
• pKa: 6.77±0.20(Predicted)
• Refractive Index: 1.8070
• Rotatable Bond Count: 0
• Topological Polar Surface Area: 68.1 Ų

Case Study

Autophagy Inhibition for Vascular Protection: Experimental Application of 3-Methyladenine in Angiotensin II-Induced Hypertensive Mice

Kwon Y, et al. Biomedicine & Pharmacotherapy, 2022, 154, 113588.

3-Methyladenine (3-MA), a classical autophagy inhibitor, has been employed experimentally to investigate the vascular impact of autophagy modulation in hypertension models. In this study, 3-MA was administered to angiotensin II (Ang II)-infused hypertensive mice to assess its role in mitigating arterial dysfunction. Experimental treatment involved chronic infusion of Ang II to induce hypertension, followed by intraperitoneal injection of 3-MA. Blood pressure was measured using a tail-cuff method, and mesenteric arteries were harvested for morphological and functional assays.
Histological analysis revealed that 3-MA reduced wall thickness and improved endothelium-dependent relaxation. Western blotting showed that Ang II elevated the autophagy markers Beclin1 and LC3 II, which were reversed by 3-MA treatment. Moreover, nitric oxide (NO) production and phosphorylation of endothelial nitric oxide synthase (eNOS Ser1177) were enhanced, as demonstrated by immunofluorescence and NO assay. Isolated mesenteric resistance arteries precontracted with U46619 or phenylephrine exhibited endothelium-dependent vasodilation upon 3-MA exposure. In vitro, vascular smooth muscle cells treated with Ang II displayed autophagy activation, which was suppressed by 3-MA, restoring p62 levels.

Experimental Application of 3‑Methyladenine in Acute Lung Injury: A Case Study on Oxidative and Apoptotic Modulation

Lei X, et al. Heliyon, 2024, 10(13), e33996.

In this study, 3‑Methyladenine (3‑MA) was systematically evaluated for its efficacy in attenuating acute lung injury (ALI) through oxidative and apoptotic control. Utilizing a dual-model approach, male C57BL/6 mice received intraperitoneal 3‑MA in a prophylactic regimen (15 mg/kg) one hour before lipopolysaccharide (LPS, 5 mg/kg) pulmonary insult. Lung histopathology, bronchoalveolar lavage fluid (BALF) assays, and TUNEL staining quantified injury severity, inflammatory infiltration, protein leakage, and apoptosis in vivo. Simultaneously, human bronchial epithelial BEAS‑2B cells were pre‑treated with 3‑MA (10 µM) one hour prior to tert‑butyl hydroperoxide (TBHP, 100 µM) exposure. Reactive oxygen species (ROS) levels were measured via DCFH‑DA fluorescence; apoptotic rates were determined by Annexin V‑FITC/PI flow cytometry. Western blotting probed caspase‑3, Bax, Bcl‑2, PKCα, NOX4, and Nrf2 expression profiles. Results demonstrated that 3‑MA pretreatment significantly reduced alveolar hemorrhage and neutrophilic accumulation, lowered BALF protein and cytokine levels (TNF‑α, IL‑6), decreased ROS fluorescence, and diminished apoptotic indices both in vivo and in vitro. Mechanistically, 3‑MA inhibited the PKCα/NOX4 axis while enhancing Nrf2 nuclear translocation, shifting the balance toward cell survival.

3-Methyladenine Suppresses Autophagy and Inflammatory Response in Intestinal Epithelium of Aged Ulcerative Colitis Mice

Liu A, et al. Experimental Gerontology, 2025, 201, 112697.

3-Methyladenine (3-MA), a classical autophagy inhibitor, was experimentally employed to evaluate its therapeutic potential in aged murine models of ulcerative colitis (UC). In this study, acute colitis was induced in both young (6-8 weeks) and aged (56 weeks) C57BL/6 mice via oral administration of 2.5% dextran sulfate sodium (DSS) for 7 days. Aged mice were intraperitoneally injected with 3-MA (15 mg/kg/day) during the induction phase. Colonic tissues were harvested for histopathological evaluation and protein expression analysis.
Autophagy levels in intestinal epithelial cells (IECs) were assessed using Western blotting for LC3B-II, p62, and ATG5, alongside immunohistochemical staining. Real-time qRT-PCR quantified pro-inflammatory mediators including TNF-α, IL-6, CCL4, and CXCL12. Furthermore, NF-κB transcriptional activity was evaluated through electrophoretic mobility shift assay (EMSA). Results demonstrated that 3-MA significantly reduced autophagic flux, dampened macrophage recruitment, and downregulated inflammatory cytokine expression in aged mice.

Custom Q&A

What is the chemical formula of 3-METHYLADENINE?

The chemical formula of 3-METHYLADENINE is C6H7N5.

What is the molecular weight of 3-METHYLADENINE?

The molecular weight of 3-METHYLADENINE is 149.15.

How can 3-METHYLADENINE be stored?

3-METHYLADENINE can be stored in a dark place, sealed in dry conditions, at room temperature.

What is the solubility of 3-METHYLADENINE?

3-METHYLADENINE is soluble in DMSO (up to 3 mg/ml) or in DMF (up to 10 mg/ml).

What is the usage of 3-METHYLADENINE?

3-METHYLADENINE is used as an autophagy inhibitor by blocking autophagosome formation via the inhibition of type III Phosphatidylinositol 3-kinases (PI-3K).

What is the general description of 3-METHYLADENINE?

3-METHYLADENINE is described as a widely used cell-permeable autophagic sequestration blocker that protects cerebellar granule cells from apoptosis following serum/potassium deprivation.

What is the safety information provided for 3-METHYLADENINE?

The Hazard Codes for 3-METHYLADENINE are Xn and the Risk Statements are 22.

What is the boiling point of 3-METHYLADENINE?

The boiling point of 3-METHYLADENINE is 240°C.

How does 3-METHYLADENINE work as an inhibitor?

3-METHYLADENINE inhibits autophagy by blocking autophagosome formation via the inhibition of type III phosphatidylinositol 3-kinases (PI-3K).