7H-purin-2-amine

• ChemBase ID: 125251
• Molecular Formular: C5H5N5
• Molecular Mass: 135.1267
• Monoisotopic Mass: 135.05449519
• SMILES: n1cc2c(nc1N)nc[nH]2
• Canonical SMILES: Nc1ncc2c(n1)nc[nH]2
• InChI: InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
• InChIKey: MWBWWFOAEOYUST-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7H-purin-2-amine; 9H-purin-2-amine
• IUPAC Traditional name: 2-aminopurine; 2-amino purine
• Synonyms: 2-Aminopurine; 9H-Purin-2-amine Dihydrochloride; Isoadenine Dihydrochloride; 2-Aminopurine Dihydrochloride; 2-AP; 2-Aminopurine; 2-氨基嘌呤

Database IDs

• CAS Number: 452-06-2; 76124-64-6
• EC Number: 207-197-4
• MDL Number: MFCD00005566
• PubChem SID: 24890778; 162219601
• PubChem CID: 9955
• CHEBI ID: 479072
• CHEMBL: 388594
• Chemspider ID: 9561
• Wikipedia Title: 2-Aminopurine

CALCULATED PROPERTIES

• Acid pKa: 10.543365
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.59066516
• LogD (pH = 7.4): -0.44963667
• Log P: -0.44668424
• Molar Refractivity: 36.2318 cm^3
• Polarizability: 13.35727 Å^3
• Polar Surface Area: 80.48 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >260°C (dec.); 280-282 °C(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: UO7475000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%
• Empirical Formula (Hill Notation): C5H5N5

DETAILS

Sigma Aldrich - A3509

Application
2-Aminopurine (2-AP) is used to specifically inhibit double-stranded RNA-dependent protein kinase, protein kinase R (PKR).

Toronto Research Chemicals - A628886

A probe of structural dynamics and charge transfer in DNA.

REFERENCES

• Kelley, S., et al.: Science, 283, 375 (1999)
• Boon, E., et al.: Nat. Biotechnol., 18, 1096 (1999)
• Jean, J., et al.: Biochemistry, 41, 13152 (1999)
• Martin, C., et al.: Methods Enzymol., 371, 13 (1999)