9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide

• ChemBase ID: 177717
• Molecular Formular: C17H22BrNO4
• Molecular Mass: 384.26488
• Monoisotopic Mass: 383.07322019
• SMILES: Br.O(C(=O)[C@@H](c1ccccc1)CO)C1CC2C3C(C(N2C)C1)O3
• Canonical SMILES: OC[C@H](c1ccccc1)C(=O)OC1CC2N(C(C1)C1C2O1)C.Br
• InChI: InChI=1S/C17H21NO4.BrH/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10;/h2-6,11-16,19H,7-9H2,1H3;1H/t11?,12-,13?,14?,15?,16?;/m1./s1
• InChIKey: WTGQALLALWYDJH-VTEZLSFDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide
• IUPAC Traditional name: 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide
• Synonyms: (αS)-α-(Hydroxymethyl)benzeneacetic Acid; Hyoscine Hydrobromide Trihydrate, (1α,2β,4β,5α,7β)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester Hydrobromide Trihydrate; Scopolammonium Bromide Trihydrate; Scopolamine Hydrobromide Trihydrate

Database IDs

• CAS Number: 114-49-8
• PubChem SID: 164233627
• PubChem CID: 11957688

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.56972116
• LogD (pH = 7.4): 0.7621961
• Log P: 0.8949523
• Molar Refractivity: 79.7213 cm^3
• Polarizability: 32.014694 Å^3
• Polar Surface Area: 62.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 193-196°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S200000

An acetylcholine antagonist. Used in treatment of motion sickness; antiemetic; antispasmodic; mydriatic; preanesthetic medicant.

REFERENCES

• Brand, J.J., et al.: Lancet, 2, 232 (1970)
• Bowles, J.B., et al.: Anaesthesia, 34, 476 (1970)
• Clissold, S.P., et al.: Drugs, 29, 189 (1970)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 19, 477 (1970)