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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 Chemical Properties |
| Melting point | 214-217 °C (decomp) | | refractive index | -24 ° (C=1, H2O) | | solubility | H2O: 50 mg/mL | | form | powder | | color | white | | optical activity | [α]25/D 25°, c = 5 in H2O(lit.) | | Merck | 14,6003 | | 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) |
| METHSCOPOLAMINE BROMIDE Usage And Synthesis |
| Originator | Pamine,Upjohn,US,1953 | | Uses | (?)-Scopolamine methyl bromide was administered to rats to inhibit the peripheral cholinergic effects induced by pilocarpine.10,11 | | Uses | anticholinergic | | Uses | METHSCOPOLAMINE BROMIDE is the methylated derivative of Scopolamine (S200000), a muscarinic antagonist that is similar to acetylcholine. METHSCOPOLAMINE BROMIDE 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: A quaternary ammonium salt resulting from the reaction of the amino group of scopolamine with methyl bromide. | | 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. |
| METHSCOPOLAMINE BROMIDE Preparation Products And Raw materials |
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