Methscopolamine bromide Chemical Properties

Melting point:

214-217 °C (decomp)

refractive index 

-24 ° (C=1, H2O)

storage temp. 

Store at -20°C

solubility 

H₂O: 50 mg/mL

form 

powder

color 

white

optical activity

[α]25/D 25°, c = 5 in H2O(lit.)

Merck 

14,6003

Stability:

Hygroscopic

CAS DataBase Reference

155-41-9

EPA Substance Registry System

3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane, 7-[(2S)-3-hydroxy-1-oxo-2-phenylpropoxy]-9,9-dimethyl-, bromide (1:1), (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)- (155-41-9)

Safety Information

Hazard Codes 

T,N,Xn

Risk Statements 

23/24/25-50/53-20/21/22-20/21

Safety Statements 

36/37/39-45-61-60-36/37

RIDADR 

UN 1544 6.1/PG 3

WGK Germany 

3

RTECS 

YM3675000

HazardClass 

6.1

PackingGroup 

III

HS Code 

29399990

MSDS

• Language:English Provider:SigmaAldrich

Methscopolamine bromide Usage And Synthesis

Chemical Properties

Methscopolamine Bromide is an anticholinergic, which occurs as white crystals, or as a white odorless crystalline powder. It melts at about 225°C with decomposition. The drug is freely soluble in water, slightly soluble in alcohol, and insoluble in acetone and in chloroform.

Originator

Pamine,Upjohn,US,1953

Uses

Methscopolamine bromide is the methylated derivative of Scopolamine, a muscarinic antagonist that is similar to acetylcholine. It have been used for the treatment of peptic ulcers by reducing acid secretion of the stomach and is used to treat morning sickness.

Definition

ChEBI: Scopolamine methyl bromide is a quaternary ammonium salt resulting from the reaction of the amino group of scopolamine with methyl bromide. It has a role as a muscarinic antagonist, an antiemetic, an antispasmodic drug and a parasympatholytic. It is a quaternary ammonium salt and a bromide salt. It is functionally related to a scopolamine.

Application

(-)-Scopolamine methyl bromide was administered to rats to inhibit the peripheral cholinergic effects induced by pilocarpine.

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.

Mode of action

methscopolamine bromide is used to treat gastrointestinal disorders such as peptic ulcers, irritable bowel syndrome, and stomach cramps. Its mechanism of action involves blocking the action of acetylcholine on smooth muscle cells in the digestive tract, thereby reducing spasms and increasing motility.

References

[1] ANDRé ROBERT JAMES E N. Effect of an anti-acetylcholine drug, methscopolamine bromide, on ulcer formation and gastric mucus[J]. Journal of Pharmacy and Pharmacology, 1964, 16 10: 690-695. DOI:10.1111/j.2042-7158.1964.tb07388.x.
[2] M A WASSERMAN R L G. Bronchospasmolytic effects of methscopolamine bromide.[J]. Journal of Pharmacology and Experimental Therapeutics, 1979, 211 1: 159-166.
[3] J A DANIEL. Methscopolamine bromide blocks hypothalamic-stimulated release of growth hormone in ewes.[J]. Journal of animal science, 1997, 75 5: 1359-1362. DOI:10.2527/1997.7551359x.

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