12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.02,6]tetradeca-1(10),3,5,8,11,13-hexaen-8-ium-8-olate

• ChemBase ID: 159745
• Molecular Formular: C17H13ClN4O
• Molecular Mass: 324.76432
• Monoisotopic Mass: 324.07778874
• SMILES: c12c(C(=[N+](Cc3n1c(nn3)C)[O-])c1ccccc1)cc(cc2)Cl
• Canonical SMILES: Clc1ccc2c(c1)C(=[N+]([O-])Cc1n2c(C)nn1)c1ccccc1
• InChI: InChI=1S/C17H13ClN4O/c1-11-19-20-16-10-21(23)17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
• InChIKey: WHYAIKHHRCPZBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-8-ium-8-olate
• IUPAC Traditional name: 12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-8-ium-8-olate
• Synonyms: 8-Chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine 5-Oxide; NSC 303007; Alprazolam 5-Oxide

Database IDs

• CAS Number: 30896-65-2
• PubChem SID: 162253880
• PubChem CID: 327554

CALCULATED PROPERTIES

• Acid pKa: 17.358156
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.6123861
• LogD (pH = 7.4): 0.6125973
• Log P: 0.6126
• Molar Refractivity: 102.3361 cm^3
• Polarizability: 33.95873 Å^3
• Polar Surface Area: 59.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid

DETAILS

Toronto Research Chemicals - A575750

A metabolite of Alprazolam (A575650).

REFERENCES

• Schwartz, M.A., et al.: J. Pharmacol. Exp. Ther., 149, 423 (1965)
• Childress, S.J., et al.: J. Pharm. Sci., 53, 577 (1965)
• Gall, M., et al.: J. Med. Chem., 21, 1290 (1978)