Scopolamine butylbromide Chemical Properties

Melting point:

142-1440C

alpha 

D20 -20.8° (c = 3 in water)

storage temp. 

2-8°C

solubility 

H₂O: 50 mg/mL

form 

powder

color 

white

optical activity

[α]25/D 20.8°, c = 3 in H2O(lit.)

CAS DataBase Reference

149-64-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

RTECS 

YM3500000

Toxicity

LD50 in mice (mg/kg): 15.6 i.v.; 74 i.p.; 570 s.c.; 3000 orally (Stockhaus, Wick)

MSDS

• Language:English Provider:Hyoscine N-butyl bromide
• Language:English Provider:SigmaAldrich

Scopolamine butylbromide Usage And Synthesis

Chemical Properties

Crystalline Solid

Originator

Butylscopolamine,China Pharm

Uses

Anticholinergic. Antispasmodic

Uses

(?)-Scopolamine N-butyl bromide was used as standard in designing a procedure for quantification of compounds using CE-MS.⁸

Manufacturing Process

1300 g of scopolamine base and 350 g of n-butylbromide in 600 ml acetonitrile is heated at 65°C for 160 hours. The oil obtained is dissolved in methanol. The solution is cooled and crystalline scopolamine N-n-butylbromide is filtered. After recrystallization from methanol was obtained scopolamine N-n-butylbromide with melting point 142-144°C and [α]d 20 = -20.5° (3% solution in water); yield 65%.

Therapeutic Function

Anticholinergic, Spasmolytic, Antitussive

Biochem/physiol Actions

Competitive muscarinic acetylcholine receptor antagonist; antispasmodic.

Clinical Use

Symptomatic relief of gastrointestinal or genitourinary disorders due to smooth muscle spasm Bowel colic
Excessive respiratory secretions

target

AChR

Drug interactions

Potentially hazardous interactions with other drugs
None known

Metabolism

The main metabolic pathway is the hydrolytic cleavage of the ester bond. Orally administered hyoscine butylbromide is excreted in the faeces and in the urine. Studies in man show that 2-5% of radioactive doses is eliminated renally after oral, and 0.7-1.6% after rectal administration. Approximately 90% of recovered radioactivity can be found in the faeces after oral administration. The urinary excretion of hyoscine butylbromide is less than 0.1% of the dose. The metabolites excreted via the renal route bind poorly to muscarinic receptors and are therefore not considered to contribute to the effect of the hyoscine butylbromide.

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