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Methscopolamine bromide

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Methscopolamine bromide Basic information
Product Name:Methscopolamine bromide
Synonyms:METHSCOPOLAMINE BROMIDE;(-)SCOPOLAMINE METHYL BROMIDE;SCOPOLAMINE METHYL BROMIDE;(-)-tropate;,9-dimethyl-,bromide,[7(s)-(1alpha,2beta,4beta,5alpha,7beta)]-;.0(2,4)]nonanebromide;1alphah,5alphah-tropanium,6beta,7beta-epoxy-3alpha-hydroxy-8-methyl-,bromide,;3-oxa-9-azoniatricyclo(3.3.1.0(2,4))nonane,7-(3-hydroxy-1-oxo-2-phenylpropoxy)
CAS:155-41-9
MF:C18H24BrNO4
MW:398.29
EINECS:205-844-5
Product Categories:Alkaloids;Biochemistry;Tropane Alkaloids;PAMINE
Mol File:155-41-9.mol
Methscopolamine bromide Structure
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 Rotation[α]25/D 25°, c = 5 in H2O(lit.)
Water Solubility H2O: 50mg/mL
Merck 14,6003
Stability:Hygroscopic
InChIKeyCXYRUNPLKGGUJF-RAFJPFSSSA-M
SMILES[Br-].[H][C@]12C[C@@H](C[C@]([H])([C@@]3([H])O[C@@]13[H])[N+]2(C)C)OC(=O)[C@H](CO)c4ccccc4
CAS DataBase Reference155-41-9
EPA Substance Registry System3-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
TSCA TSCA listed
HazardClass 6.1
PackingGroup III
HS Code 29399990
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Aquatic Acute 1
MSDS Information
ProviderLanguage
SigmaAldrich English
Methscopolamine bromide Usage And Synthesis
Chemical PropertiesMethscopolamine 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.
OriginatorPamine,Upjohn,US,1953
UsesMethscopolamine 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.
DefinitionChEBI: 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 ProcessIn 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 FunctionSpasmolytic
Biochem/physiol ActionsCompetitive muscarinic acetylcholine receptor antagonist.
Mode of actionmethscopolamine 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.
Methscopolamine bromide Preparation Products And Raw materials
Raw materialsMethyl bromide-->Scopolamine Hydrobromide Trihydrate
Tag:Methscopolamine bromide(155-41-9) Related Product Information
Scopolamine Hydrobromide Trihydrate N-METHYLPIPERIDINE-2-ETHANOL (S)-(+)-1-Methyl-3-pyrrolidinol HYOSCYAMINE HYDROBROMIDE ATROPINE METHYL BROMIDE Cimetropium bromide (S)-3-Hydroxypyrrolidine ANISODAMINE HYDROBROMIDE (R)-(+)-PIPERIDINE-2-ETHANOL Methscopolamine bromide 3S-3-METHYLMORPHOLINE L-Hyoscyamine 1-Methyl-2-pyrrolidineethanol 2-Piperidineethanol Scopolamine hydrobromide Scopine 3-methylmorpholine Atropine

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