(4Z)-9-(2-chlorophenyl)-4-[(4-methylpiperazin-1-yl)methylidene]-12-nitro-2,5,8-triazatricyclo[8.4.0.02,6]tetradeca-1(14),5,8,10,12-pentaen-3-one

• ChemBase ID: 172379
• Molecular Formular: C23H21ClN6O3
• Molecular Mass: 464.90424
• Monoisotopic Mass: 464.13636624
• SMILES: c1c(cc2c(c1)N1C(=N/C(=C\N3CCN(CC3)C)/C1=O)CN=C2c1ccccc1Cl)[N+](=O)[O-]
• Canonical SMILES: CN1CCN(CC1)/C=C/1\N=C2N(C1=O)c1ccc(cc1C(=NC2)c1ccccc1Cl)[N+](=O)[O-]
• InChI: InChI=1S/C23H21ClN6O3/c1-27-8-10-28(11-9-27)14-19-23(31)29-20-7-6-15(30(32)33)12-17(20)22(25-13-21(29)26-19)16-4-2-3-5-18(16)24/h2-7,12,14H,8-11,13H2,1H3/b19-14-
• InChIKey: UTEFBSAVJNEPTR-RGEXLXHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4Z)-9-(2-chlorophenyl)-4-[(4-methylpiperazin-1-yl)methylidene]-12-nitro-2,5,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),5,8,10,12-pentaen-3-one
• IUPAC Traditional name: loprazolam
• Synonyms: (2Z)-6-(2-Chlorophenyl)-2,4-dihydro-2-[(4-methyl-1-piperazinyl)methylene]-8-nitro-1H-imidazo[1,2-a][1,4]benzodiazepin-1-one; RU 31158; Loprazolam

Database IDs

• CAS Number: 61197-73-7
• PubChem SID: 164228289
• PubChem CID: 3033860

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.16316712
• LogD (pH = 7.4): 1.9330547
• Log P: 2.6784084
• Molar Refractivity: 126.868 cm^3
• Polarizability: 46.818306 Å^3
• Polar Surface Area: 97.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Orange Red Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L469510

Sedative, hypnotic. Controlled substance (depressant).

REFERENCES

• Clark, B.G., et al.: Drugs, 31, 500 (1977)
• Agar, J.R., et al.: J. Med. Chem., 20, 1035 (1977)