9-butyl-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium bromide

• ChemBase ID: 163490
• Molecular Formular: C21H30BrNO4
• Molecular Mass: 440.3712
• Monoisotopic Mass: 439.13582045
• SMILES: O(C(=O)[C@H](CO)c1ccccc1)C1CC2C3C(C(C1)[N+]2(CCCC)C)O3.[Br-]
• Canonical SMILES: CCCC[N+]1(C)C2CC(CC1C1C2O1)OC(=O)[C@@H](c1ccccc1)CO.[Br-]
• InChI: InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15?,16-,17?,18?,19?,20?,22?;/m1./s1
• InChIKey: HOZOZZFCZRXYEK-BITHUKPRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-butyl-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-9-ium bromide
• IUPAC Traditional name: 9-butyl-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-9-ium bromide
• Synonyms: 7(S)-(1α,2β,4β,5α,7β)]-9-Butyl-7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane Bromide; (-)-Scopolamine Butylbromide; Amisepan; Buscopan; N-Butylhyoscinium Bromide; Stibron; Tirantil; N-Butylscopolammonium Bromide

Database IDs

• CAS Number: 149-64-4
• PubChem SID: 162257625
• PubChem CID: 11957696

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.9434853
• LogD (pH = 7.4): -1.9434851
• Log P: -1.9434853
• Molar Refractivity: 109.5085 cm^3
• Polarizability: 39.308178 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B693750

Anticholinergic. Antispasmodic.

REFERENCES

• Lee, J.R., et al.: Clin. Radiol., 33, 273 (1982)
• Bauer, et al.: Arzneim.-Forsch., 18, 1132 (1982)
• Steger, A.C., et al.: Am. J. Gastroenterol., 81, 615 (1982)