(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide

• ChemBase ID: 73053
• Molecular Formular: C17H22BrNO4
• Molecular Mass: 384.26488
• Monoisotopic Mass: 383.07322019
• SMILES: O(C(=O)[C@@H](c1ccccc1)CO)[C@H]1C[C@H]2[C@H]3[C@@H]([C@H](N2C)C1)O3.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.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-HXIZEQBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide; (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 hydrobromide
• IUPAC Traditional name: scopolamine hydrobromide; (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 hydrobromide
• Synonyms: Scopolamine hydrobromide; HYOSCINE HYDROBROMIDE

Database IDs

• CAS Number: 114-49-8; 114-49-8
• EC Number: 204-050-6
• PubChem SID: 162037973
• PubChem CID: 6603108

CALCULATED PROPERTIES

• 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
• 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

PROPERTIES

Physical Property

• Melting Point: 196°C

Safety Information

• Storage Condition: -20°C
• RTECS: YM4550000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:36/37/39

Product Information

• Salt Data: hydrobromide

DETAILS

MP Biomedicals - 05210273

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2508

Research Area: Neurological Disease
Biological Activity:
Scopolamine is a competitive muscarinic acetylcholine receptor with an IC50 of 55.3 ± 4.3 nM. It is a tropane alkaloid drug with muscarinic antagonist effects. It is among the secondary metabolites of plants from Solanaceae (nightshade) family of plants, such as henbane, jimson weed and Angel’s Trumpets (Datura resp. Brugmansia spec.), and corkwood (Duboisia species). It exerts its effects by acting as a competitive antagonist at muscarinic acetylcholine receptors, specifically M1 receptors; it is thus classified as an anticholinergic, anti-muscarinic drug. [1][2]

REFERENCES

• Sim MK et al. Eur J Pharmacol. 1990 Dec 15;189(6)