3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium hydrate bromide

• ChemBase ID: 171731
• Molecular Formular: C20H32BrNO4
• Molecular Mass: 430.37638
• Monoisotopic Mass: 429.15147051
• SMILES: [Br-].O.C(CO)(C(=O)OC1CC2CCC([N+]2(C(C)C)C)C1)c1ccccc1
• Canonical SMILES: OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)[N+]2(C)C(C)C.O.[Br-]
• InChI: InChI=1S/C20H30NO3.BrH.H2O/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H;1H2/q+1;;/p-1
• InChIKey: KEWHKYJURDBRMN-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium hydrate bromide
• IUPAC Traditional name: 3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-methyl-8-azabicyclo[3.2.1]octan-8-ium hydrate bromide
• Synonyms: (3-endo,8-syn)-3-(3-Hydroxy-1-oxo-2-phenylpropyl)-8-methyl-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane Bromode Monohydrate; Atropine Isopropyl Bromide; Ipratropium Bromide Monohydrate

Database IDs

• CAS Number: 922491-06-3
• PubChem SID: 164227641
• PubChem CID: 441337

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.8177127
• LogD (pH = 7.4): -1.8177124
• Log P: -1.8177127
• Molar Refractivity: 105.8974 cm^3
• Polarizability: 37.49658 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 232-237°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I740500

N-Isopropyl quaternary salt of Atropine. Nonselective muscarinic acetylcholine receptor antagonist; bronchodilator.

REFERENCES

• Groeben, H., et al.: Anesthesiology, 85, 867 (1996)
• Haddad, et al.: Br. J. Pharmacol., 127, 413 (1996)
• Barnes, P. J., et al.: Chest, 117, 63S (1996)