155-41-9 Usage
Description
METHSCOPOLAMINE BROMIDE, also known as (±)-Scopolamine methyl bromide, is a quaternary ammonium salt that is derived from the reaction of the amino group of scopolamine with methyl bromide. It is a muscarinic antagonist that is structurally similar to acetylcholine and possesses anticholinergic properties.
Uses
Used in Pharmaceutical Industry:
METHSCOPOLAMINE BROMIDE is used as an anticholinergic agent for its ability to inhibit the peripheral cholinergic effects induced by pilocarpine in rats. This property makes it useful in the treatment of various conditions that involve overactivity of the parasympathetic nervous system.
Used in Gastroenterology:
METHSCOPOLAMINE BROMIDE is used as a medication for the treatment of peptic ulcers. It functions by reducing the acid secretion of the stomach, which helps in the healing process of the ulcers and alleviates the associated symptoms.
Used in Obstetrics:
METHSCOPOLAMINE BROMIDE is used as a treatment for morning sickness during pregnancy. Its anticholinergic properties help in reducing the symptoms of nausea and vomiting, providing relief to pregnant women experiencing this condition.
Originator
Pamine,Upjohn,US,1953
Manufacturing Process
In a one-liter separatory funnel, 94 g (0.215 mol) of scopolamine
hydrobromide trihydrate was dissolved in 250 ml of water, made alkaline by
shaking with 40 g (1 mol) of sodium hydroxide in 150 ml of water, and the
free base immediately extracted with ether. As scopolamine is somewhat
soluble in water, the aqueous layer was saturated with potassium carbonate
and again extracted with ether. The combined ether extracts were dried over
anhydrous magnesium sulfate and the ether removed by distillation, leaving
65 g (0.214 mol; 100% yield) of nearly colorless oil. Then 100 g (1.05 mols)
of cold methyl bromide was added to a chilled, 500-ml pressure flask
containing the 65 g of scopolamine, the flask stoppered tightly with a clamp,
and allowed to stand at room temperature for 96 hours.
The flask was cooled before opening, excess methyl bromide removed by
filtration, and the white solid washed thoroughly with dry ether. The yield of
crude scopolamine methyl bromide was 80g (94% yield; 93.5% over-all
yield).
The salt was recrystallized from 550 ml of alcohol; first crop, 70 g, MP 212° to
214°C; second crop, 6 g, MP 195° to 200°C. The combined crops were again
recrystallized from 500 ml of 3-A alcohol; MP 210° to 212°C. The third
recrystallization from 600 ml of alcohol yielded 64 g, MP 214° to 216°C, a
75% yield based on scopolamine hydrobromide trihydrate starting material.
Therapeutic Function
Spasmolytic
Biochem/physiol Actions
Competitive muscarinic acetylcholine receptor antagonist.
Check Digit Verification of cas no
The CAS Registry Mumber 155-41-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 5 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 155-41:
(5*1)+(4*5)+(3*5)+(2*4)+(1*1)=49
49 % 10 = 9
So 155-41-9 is a valid CAS Registry Number.
InChI:InChI=1/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