6-(methylsulfanyl)-9H-purin-2-amine

• ChemBase ID: 133537
• Molecular Formular: C6H7N5S
• Molecular Mass: 181.21828
• Monoisotopic Mass: 181.04221625
• SMILES: CSc1c2c([nH]cn2)nc(n1)N
• Canonical SMILES: CSc1nc(N)nc2c1nc[nH]2
• InChI: InChI=1S/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
• InChIKey: YEGKYFQLKYGHAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(methylsulfanyl)-9H-purin-2-amine; 6-(methylsulfanyl)-7H-purin-2-amine
• IUPAC Traditional name: 6-(methylsulfanyl)-9H-purin-2-amine; 6-(methylsulfanyl)-7H-purin-2-amine
• Synonyms: 2-Amino-6-methylthiopurine; 2-Amino-6-methylmercaptopurine; 6-(Methylthio)-1H-purin-2-amine; 2-Amino-6-methylmercaptopurine; NSC 29420; S-Methyl-6-thioguanine; S6-Methyl-6-thioguanine; 6-Methylthioguanine

Database IDs

• CAS Number: 1198-47-6
• EC Number: 214-833-4
• MDL Number: MFCD00044701
• PubChem SID: 162227814; 24891471
• PubChem CID: 70976

CALCULATED PROPERTIES

• Acid pKa: 10.575983
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7333762
• LogD (pH = 7.4): 0.733271
• Log P: 0.7335329
• Molar Refractivity: 50.9244 cm^3
• Polarizability: 18.26473 Å^3
• Polar Surface Area: 80.48 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95%

DETAILS

Sigma Aldrich - A9546

Application
2-Amino-6-methylmercaptopurine is a 2-amino-6-alkyldithiopurine that has been used with other 6-position carbon analogues to study brain specific diazepam binding.

Toronto Research Chemicals - M330720

A metabolite of 2’-Deoxy-6-thio Guanosine (D281650) and 6-Thioguanine. An effective immunosuppressant and anticancer agent, however chronic exposure can be mutagenic in human cells as long-term use of thiopurines was found to be associated with a signific

REFERENCES

• Loo, T.L. et al.: Cancer Chemother. Pharmacol., 6, 131 (1981)
• Yuan, B. et al.: ACS Chem. Biol., 5, 1021 (1981)
• Kroplin, T. et al.: Adv. Exp. Med. Biol., 431, 741 (1981)