tert-butyl (7S)-14-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

• ChemBase ID: 153172
• Molecular Formular: C19H20BrN3O3
• Molecular Mass: 418.2844
• Monoisotopic Mass: 417.06880352
• SMILES: CC(C)(C)OC(=O)c1c2n(cn1)c1cccc(c1C(=O)N1[C@H]2CCC1)Br
• Canonical SMILES: O=C(c1ncn2c1[C@@H]1CCCN1C(=O)c1c2cccc1Br)OC(C)(C)C
• InChI: InChI=1S/C19H20BrN3O3/c1-19(2,3)26-18(25)15-16-13-8-5-9-22(13)17(24)14-11(20)6-4-7-12(14)23(16)10-21-15/h4,6-7,10,13H,5,8-9H2,1-3H3/t13-/m0/s1
• InChIKey: LWUDDYHYYNNIQI-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (7S)-14-bromo-12-oxo-2,4,11-triazatetracyclo[11.4.0.0^2,^6.0^7,^1^1]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate
• IUPAC Traditional name: bretazenil
• Synonyms: 9H-Imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid; Ro 16-6028; Bretazenil

Database IDs

• CAS Number: 84379-13-5
• MDL Number: MFCD00866987
• PubChem SID: 162247311
• PubChem CID: 107926

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8654448
• LogD (pH = 7.4): 1.8676715
• Log P: 1.8677
• Molar Refractivity: 111.6032 cm^3
• Polarizability: 38.92734 Å^3
• Polar Surface Area: 64.43 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble24 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• RTECS: NJ5899850
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C19H20N3O3Br

DETAILS

Sigma Aldrich - B6434

Biochem/physiol Actions
Bretazenil is a benzodiazepine partial agonist.