(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate trihydrate hydrobromide

• ChemBase ID: 156737
• Molecular Formular: C17H28BrNO7
• Molecular Mass: 438.31072
• Monoisotopic Mass: 437.10491424
• SMILES: CN1[C@@H]2C[C@H](C[C@H]1[C@H]1[C@@H]2O1)OC(=O)[C@H](CO)c1ccccc1.O.O.O.Br
• Canonical SMILES: OC[C@H](c1ccccc1)C(=O)O[C@@H]1C[C@H]2N([C@@H](C1)[C@H]1[C@@H]2O1)C.O.O.O.Br
• InChI: InChI=1S/C17H21NO4.BrH.3H2O/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;3*1H2/t11-,12-,13-,14+,15-,16+;;;;/m1..../s1
• InChIKey: LACQPOBCQQPVIT-SEYKEWMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate trihydrate hydrobromide
• IUPAC Traditional name: (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate trihydrate hydrobromide
• Synonyms: Hyoscine hydrobromide; Scopine tropate; (-)-Scopolamine hydrobromide trihydrate; 天仙子碱 氢溴酸盐; 莨菪胺; (-)-东莨菪碱 氢溴酸盐 三水合物

Database IDs

• CAS Number: 6533-68-2
• MDL Number: MFCD00150066
• Beilstein Number: 6100669
• PubChem SID: 162250874; 24888267
• PubChem CID: 20055509

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

• Melting Point: 195-199 °C (dry matter)(lit.)
• Optical Rotation: [α]20/D -23±2°, c = 5% in H2O

Safety Information

• RTECS: YM4730000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 26/27/28
• Safety Statements: 25-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3

Product Information

• Purity: ≥98.0% (TLC)
• Grade: purum
• Empirical Formula (Hill Notation): C17H21NO4 · HBr · 3H2O

DETAILS

Sigma Aldrich - 84785

Biochem/physiol Actions
Competitive nonselective muscarinic acetylcholine antagonist. Scopolamine-induced amnesia in laboratory animals is a commonly-used model of memory deficit.