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

• ChemBase ID: 133776
• Molecular Formular: C17H22ClNO4
• Molecular Mass: 339.81388
• Monoisotopic Mass: 339.12373587
• SMILES: CN1[C@H]2C[C@H](C[C@@H]1[C@H]1[C@@H]2O1)OC(=O)[C@H](CO)c1ccccc1.Cl
• 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.Cl
• InChI: InChI=1S/C17H21NO4.ClH/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: KXPXJGYSEPEXMF-MOUKNHLCSA-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 hydrochloride
• 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 hydrochloride
• Synonyms: (-)-Scopolamine hydrochloride; 天仙子碱 盐酸盐; 莨菪胺; (-)-东莨菪碱 盐酸盐

Database IDs

• CAS Number: 55-16-3
• EC Number: 200-225-6
• MDL Number: MFCD00058096
• Beilstein Number: 4168778
• PubChem SID: 24899457; 162228053
• PubChem CID: 6852406

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: H2O: soluble50 mg/mL
• Apperance: white powder
• Flash Point: 170.6 °F; 77 °C
• Optical Rotation: [α]25/D ~-27°, c = 1 in H2O(lit.)

Safety Information

• RTECS: CY1634501
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 26/27/28
• Safety Statements: 28-36/37-45
• 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, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - S1013

Caution
The powder is stable at least four years stored at room temperature.
Biochem/physiol Actions
Competitive nonselective muscarinic acetylcholine antagonist. Scopolamine-induced amnesia in laboratory animals is a commonly-used model of memory deficit.