7-chloro-2-(methylamino)-5-(2H5)phenyl-3H-1,4-benzodiazepin-4-ium-4-olate

• ChemBase ID: 164063
• Molecular Formular: C16H14ClN3O
• Molecular Mass: 299.75486
• Monoisotopic Mass: 299.08253976
• SMILES: c1c(cc2c(c1)N=C(C[N+](=C2c1ccccc1)[O-])NC)Cl
• Canonical SMILES: CNC1=Nc2ccc(cc2C(=[N+](C1)[O-])c1ccccc1)Cl
• InChI: InChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19)
• InChIKey: ANTSCNMPPGJYLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-2-(methylamino)-5-(^2H₅)phenyl-3H-1,4-benzodiazepin-4-ium-4-olate
• IUPAC Traditional name: 7-chloro-2-(methylamino)-5-(^2H₅)phenyl-3H-1,4-benzodiazepin-4-ium-4-olate
• Synonyms: 7-Chloro-N-methyl-5-(phenyl-d5)-3H-1,4-benzodiazepin-2amine-4-oxide; Azepoxide-d5; Clopoxide-d5; Helogaphen-d5; Libritabs-d5; Multum-d5; Risolid-d5; Chlordiazepoxide-d5

Database IDs

• CAS Number: 65891-81-8
• PubChem SID: 162258198
• PubChem CID: 45038609

CALCULATED PROPERTIES

• Acid pKa: 18.524357
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.132898
• LogD (pH = 7.4): 3.0075474
• Log P: 3.050551
• Molar Refractivity: 87.3403 cm^3
• Polarizability: 31.54656 Å^3
• Polar Surface Area: 53.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 241-2430C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - C327052

Controlled substance (depressant). Anxiolytic. Prototype of the benzodiazepine anxiolytics.

REFERENCES

• MacDonald, A., et al.: Anal. Profiles Drug Subs., 1, 15 (1972)
• Greenblatt, D.J., et al.: Clin. Pharmacokinet., 3, 381 (1972)