12-chloro-9-(2-fluorophenyl)-3-(13C)methyl(3,6,7-13C3,8-15N)-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(14),3,5,8,10,12-hexaene; but-2-enedioic acid

• ChemBase ID: 153208
• Molecular Formular: C22H17ClFN3O4
• Molecular Mass: 446.80351145
• Monoisotopic Mass: 446.09961618
• SMILES: [13CH3][13c]1nc[13c]2n1c1ccc(cc1C(=[15N][13CH2]2)c1ccccc1F)Cl.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: Clc1ccc2c(c1)C(=[15N][13CH2][13c]1n2[13c]([13CH3])nc1)c1ccccc1F.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C18H13ClFN3.C4H4O4/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13;5-3(6)1-2-4(7)8/h2-9H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/i1+1,10+1,11+1,13+1,22+1
• InChIKey: XYGVIBXOJOOCFR-UOKYZMBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 12-chloro-9-(2-fluorophenyl)-3-(^1^3C)methyl(3,6,7-^1^3C₃,8-^1^5N)-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,8,10,12-hexaene; but-2-enedioic acid
• IUPAC Traditional name: 12-chloro-9-(2-fluorophenyl)-3-(^1^3C)methyl(3,6,7-^1^3C₃,8-^1^5N)-2,4,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(14),3,5,8,10,12-hexaene; butenedioic acid
• Synonyms: 8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine, (13C4,15N)-labeled fumarate salt; Midazolam-(methyl,1,3a,4-13C4-5-15N) maleate salt

Database IDs

• MDL Number: MFCD08276929
• PubChem SID: 162247347; 24900688
• PubChem CID: 71311613

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4297755
• LogD (pH = 7.4): 3.2779806
• Log P: 3.3348
• Molar Refractivity: 99.4297 cm^3
• Polarizability: 33.933826 Å^3
• Polar Surface Area: 30.18 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to off-white solid
• Mass Shift: M+5

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (excluding maleic acid, HPLC)
• Empirical Formula (Hill Notation): C1413C4H13ClFN215N · C4H4O4

DETAILS

Sigma Aldrich - UC601

Biochem/physiol Actions
Sedative/hypnotic; ligand for the GABAA receptor benzodiazepine modulatory site; CYP3A4 substrate.