(1R,2R,4S,5S,7R)-9-butyl-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium bromide

• ChemBase ID: 73002
• Molecular Formular: C21H30BrNO4
• Molecular Mass: 440.3712
• Monoisotopic Mass: 439.13582045
• SMILES: [Br-].c1c(cccc1)[C@H](C(=O)O[C@H]1C[C@H]2[C@H]3[C@@H]([C@H]([N+]2(CCCC)C)C1)O3)CO
• Canonical SMILES: CCCC[N+]1(C)[C@@H]2C[C@H](C[C@H]1[C@H]1[C@@H]2O1)OC(=O)[C@@H](c1ccccc1)CO.[Br-]
• InChI: InChI=1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15-,16-,17?,18?,19-,20+,22?;/m1./s1
• InChIKey: HOZOZZFCZRXYEK-DNBOENQGSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 149-64-4
• EC Number: 205-744-1
• MDL Number: MFCD00078561
• PubChem SID: 24277872; 162037922
• PubChem CID: 6852391

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.9434853
• LogD (pH = 7.4): -1.9434851
• Log P: -1.9434853
• Molar Refractivity: 109.5085 cm^3
• Polarizability: 39.308178 Å^3
• Polar Surface Area: 59.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder
• Optical Rotation: [α]25/D -20.8°, c = 3 in H2O(lit.)

Safety Information

• Storage Condition: -20°C
• RTECS: YM3500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: ≥98% (TLC)
• Salt Data: bromide

DETAILS

Selleck Chemicals - S2378

Research Area: Neurological Disease
Biological Activity:
Butylscopolamine bromide, is a peripherally acting antimuscarinic, anticholinergic agent used as an abdominal-specific antispasmodic. It is a quaternary ammonium compound and a semisynthetic derivative of scopolamine.Butylscopolamine is used to treat pain and discomfort caused by abdominal cramps, menstrual cramps, or other spasmodic activity in the digestive system. It is also effective at preventing bladder spasms. [1]

Sigma Aldrich - S7882

Biochem/physiol Actions
Competitive muscarinic acetylcholine receptor antagonist; antispasmodic.

REFERENCES

• http://en.wikipedia.org/wiki/Butylscopolamine