(1R,3R,5S,8S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-(2H3)methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium iodide

• ChemBase ID: 171732
• Molecular Formular: C20H30INO3
• Molecular Mass: 459.36157
• Monoisotopic Mass: 459.12704183
• SMILES: [I-].C(CO)(C(=O)O[C@H]1C[C@H]2CC[C@H]([N@+]2(C(C)C)C)C1)c1ccccc1
• Canonical SMILES: OCC(c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)[N@+]2(C)C(C)C.[I-]
• InChI: InChI=1S/C20H30NO3.HI/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/q+1;/p-1/t16-,17+,18+,19?,21+
• InChIKey: YLJVWJKSALOVFB-VVQPYUEFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5S,8S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-(^2H₃)methyl-8-(propan-2-yl)-8-azabicyclo[3.2.1]octan-8-ium iodide
• IUPAC Traditional name: (1R,3R,5S,8S)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8-isopropyl-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octan-8-ium iodide
• Synonyms: (3-endo,8-syn)-3-(3-Hydroxy-1-oxo-2-phenylpropoxy)-8-(methyl-d3)-8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octane Iodide; Ipratropium-d3 Iodide

Database IDs

• PubChem SID: 164227642
• PubChem CID: 71749524

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 to Off-White Solid
• Melting Point: 216-218°C

Safety Information

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

DETAILS

Toronto Research Chemicals - I740502

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)