(1R,2R,4S,5S,7S)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium bromide

• ChemBase ID: 133935
• Molecular Formular: C18H24BrNO4
• Molecular Mass: 398.29146
• Monoisotopic Mass: 397.08887025
• SMILES: C[N+]1([C@@H]2C[C@H](C[C@H]1[C@H]1[C@@H]2O1)OC(=O)[C@H](CO)c1ccccc1)C.[Br-]
• Canonical SMILES: OC[C@H](c1ccccc1)C(=O)O[C@@H]1C[C@@H]2[C@@H]3[C@H]([C@H](C1)[N+]2(C)C)O3.[Br-]
• InChI: InChI=1S/C18H24NO4.BrH/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11;/h3-7,12-17,20H,8-10H2,1-2H3;1H/q+1;/p-1/t12-,13-,14-,15+,16-,17+;/m1./s1
• InChIKey: CXYRUNPLKGGUJF-RAFJPFSSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,4S,5S,7S)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-9-ium bromide
• IUPAC Traditional name: (1R,2R,4S,5S,7S)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-9-ium bromide
• Synonyms: Hyoscine methyl bromide; Methscopolamine bromide; (-)-Scopolamine methyl bromide

Database IDs

• CAS Number: 155-41-9
• EC Number: 205-844-5
• MDL Number: MFCD00078560
• PubChem SID: 162228212; 24278714
• PubChem CID: 5459110

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -3.2673843
• LogD (pH = 7.4): -3.2673843
• Log P: -3.2673843
• Molar Refractivity: 95.6349 cm^3
• Polarizability: 33.79425 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder
• Optical Rotation: [α]25/D -25°, c = 5 in H2O(lit.)

Safety Information

• RTECS: YM3675000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 20/21-50/53
• Safety Statements: 36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H312 + H332-H400
• GHS Precautionary statements: P273-P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 1544 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - S8502

Biochem/physiol Actions
Competitive muscarinic acetylcholine receptor antagonist.
Caution
Shelf-life of the powder is at least five years when stored at room temperature.