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Methscopolamine bromide

Product Name
Methscopolamine bromide
CAS No.
155-41-9
Chemical Name
Methscopolamine bromide
Synonyms
blocan;diopal;nutrop;pamine;ampyrox;holopan;holopon;mescopil;paraspan;-tropate
CBNumber
CB0746986
Molecular Formula
C18H24BrNO4
Formula Weight
398.29
MOL File
155-41-9.mol
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Methscopolamine bromide Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H400Very toxic to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
S8502
Product name
(?)-Scopolamine methyl bromide
Purity
≥98% (HPLC), powder
Packaging
1g
Price
$81.4
Updated
2024/03/01
Sigma-Aldrich
Product number
1421009
Product name
Methscopolamine bromide
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
S0231
Product name
Scopolamine Methyl Bromide
Purity
>98.0%(T)
Packaging
1g
Price
$73
Updated
2024/03/01
Cayman Chemical
Product number
23862
Product name
Methylscopolamine (bromide)
Purity
≥98%
Packaging
500mg
Price
$40
Updated
2024/03/01
Cayman Chemical
Product number
23862
Product name
Methylscopolamine (bromide)
Purity
≥98%
Packaging
1g
Price
$72
Updated
2024/03/01
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Methscopolamine bromide Chemical Properties,Usage,Production

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.

Methscopolamine bromide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Methscopolamine bromide manufacturers

Career Henan Chemical Co
Product
METHSCOPOLAMINE BROMIDE 155-41-9
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

155-41-9, Methscopolamine bromideRelated Search:

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

  • 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)
  • 3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane,7-(3-hydroxy-1-oxo-2-phenyl-
  • 3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane,7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9
  • 5-alpha-h-tropanium,6-beta,7-beta-epoxy-3-alpha-hydroxy-8-methyl-1-alpha-b
  • 5-alpha-h-tropanium,6-beta,7-beta-epoxy-3-alpha-hydroxy-8-methyl-1-alpha-br
  • 6beta,7beta-epoxy-3alpha-hydroxy-8-methyl-1alphah,5alphah-tropaniumbromide(-)
  • 7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9,9-dimethyl-3-oxo-9-azoniatricyclo-[3.3.1
  • -9,9-dimethyl-,bromide,(7(s)-(1alpha,2bet///
  • ampyrox
  • blocan
  • diopal
  • epoxymethaminebromide
  • epoxytropinetropatemethylbromide
  • holopan
  • holopon
  • lescopinebromide
  • mescopil
  • methoscopylaminebromide
  • methylbromidescopolamine
  • methylscopolaminebromide
  • methylscopolaminehydrobromide
  • neo-avagal
  • n-methylhyoscinebromide
  • n-methylscopolammoniumbromide
  • nutrop
  • omide,(-)-tropate(ester)
  • pamine
  • paminebromide
  • N-methylhyoscinium bromide
  • (-)-SCOPOLAMINE METHYL BROMIDE CHOLINERG IC ANTAGONIS
  • Hyoscine methobromide
  • Hyoscine methyl bromide, Methscopolamine bromide
  • (-)-Tropate(ester)
  • 1.alpha.-H,5.alpha.H-Tropanium, 6.beta.,7.beta.-epoxy-3.alpha.-hydroxy-8-methyl-, bromide, (-)-tropate
  • 1.alpha.H,5.alpha.H-Tropanium, 6.beta.,7.beta.-epoxy-3.alpha.-hydroxy-8-methyl-, bromide, (-)-tropate
  • 3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane, 7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9,9-dimethyl-, bromide, [7(S)-(1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)]-
  • Methscopolamine Bromide (200 mg)
  • 3-Oxa-9-azoniatricyclo3.3.1.02,4nonane, 7-(2S)-3-hydroxy-1-oxo-2-phenylpropoxy-9,9-dimethyl-, bromide, (1.alpha.,2.beta.,4.beta.,5.alpha.,7.beta.)-
  • (-)-Scopolaminmethylbromid
  • HYOSCINE METHYL BROMIDE
  • Hyoscine Butylbromide Impurity C
  • (1α,2β,4β,5α,7β)-7-[(2S)-3-hydroxy-1-oxo-2-phenylpropoxy]-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane, bromide (1:1)
  • paraspan
  • proscomide
  • restropin
  • romide,(-)-tropate(ester)
  • scopolaminemethobromide
  • -tropate
  • Hyoscine Hydrobromide EP Impurity C
  • Oxitropium bromide impurity B CRS
  • Homatropine Methylbromide EP Impurity D