1-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-amine

• ChemBase ID: 132373
• Molecular Formular: C7H8N4
• Molecular Mass: 148.16522
• Monoisotopic Mass: 148.07489628
• SMILES: Cn1cnc(c2ccnc12)N
• Canonical SMILES: Cn1cnc(c2c1ncc2)N
• InChI: InChI=1S/C7H8N4/c1-11-4-10-6(8)5-2-3-9-7(5)11/h2-4H,8H2,1H3
• InChIKey: SNBXPRWTKZJKKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-amine
• IUPAC Traditional name: 1-methylpyrrolo[2,3-d]pyrimidin-4-amine
• Synonyms: 3-MA; 6-Amino-3-methylpurine; 3-Methyladenine

Database IDs

• CAS Number: 5142-23-4
• EC Number: 225-908-6
• MDL Number: MFCD00010531
• Beilstein Number: 146087
• PubChem SID: 24897326; 162226650
• PubChem CID: 12662857

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.012556344
• LogD (pH = 7.4): 0.012649752
• Log P: 0.012650943
• Molar Refractivity: 43.0468 cm^3
• Polarizability: 15.965805 Å^3
• Polar Surface Area: 56.73 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~300 °C (dec.)(lit.)

Safety Information

• RTECS: AU6520000
• German water hazard class: 3

Product Information

• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - M9281

Preparation Note
This product is soluble in DMF (10 mg/ml, may require gentle heating), yielding a clear, colorless solution. It is also soluble in water, 95% ethanol, or 1 N NaOH at 30 mg/ml with heating, but upon cooling, the product precipitates from solution. Solutions of 3-MA are best prepared fresh.
Application
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). For use as an autophagy inhibitor, 3-MA is typically used at a concentration of 5 mM.