CHEBI:61276 - scopolamine methobromide

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ChEBI Name scopolamine methobromide
ChEBI ID CHEBI:61276
Definition A quaternary ammonium salt resulting from the reaction of the amino group of scopolamine with methyl bromide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H24BrNO4
Net Charge 0
Average Mass 398.29100
Monoisotopic Mass 397.08887
InChI InChI=1S/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
InChIKey CXYRUNPLKGGUJF-RAFJPFSSSA-M
SMILES [Br-].C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)c1ccccc1
Roles Classification
Biological Role(s): muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
Application(s): muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
antispasmodic drug
A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
parasympatholytic
Any cholinergic antagonist that inhibits the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the muscarinic antagonists.
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ChEBI Ontology
Outgoing scopolamine methobromide (CHEBI:61276) has functional parent scopolamine (CHEBI:16794)
scopolamine methobromide (CHEBI:61276) has role antiemetic (CHEBI:50919)
scopolamine methobromide (CHEBI:61276) has role antispasmodic drug (CHEBI:53784)
scopolamine methobromide (CHEBI:61276) has role muscarinic antagonist (CHEBI:48876)
scopolamine methobromide (CHEBI:61276) has role parasympatholytic (CHEBI:50370)
scopolamine methobromide (CHEBI:61276) is a bromide salt (CHEBI:22925)
scopolamine methobromide (CHEBI:61276) is a quaternary ammonium salt (CHEBI:35273)
IUPAC Name
(1R,2R,4S,5S,7s)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane
INN Source
hyoscine methobromide KEGG DRUG
Synonyms Sources
(−)-(1S,3s,5R,6R,7S)-6,7-epoxy-8-methyl-3-[(S)-tropoyloxy]tropanium bromide ChEBI
(−)-scopolamine methobromide ChEBI
(−)-scopolamine methyl bromide ChemIDplus
(S)-6β,7β-epoxy-8-methyl-3α-(−)-tropoyloxy-1αH,5αH-tromanium bromide ChemIDplus
hyoscine methyl bromide ChemIDplus
methscopolamine bromide ChemIDplus
methylscopolamine bromide ChemIDplus
N-methylhyoscine bromide DrugBank
N-methylscopolammonium bromide ChemIDplus
scopolamine methyl bromide ChEBI
Brand Name Source
Pamine KEGG DRUG
Manual Xrefs Databases
D00715 KEGG DRUG
DB00462 DrugBank
DB00747 DrugBank
US2753288 Patent
View more database links
Registry Numbers Types Sources
155-41-9 CAS Registry Number KEGG DRUG
155-41-9 CAS Registry Number ChemIDplus
8173227 Reaxys Registry Number Reaxys
Last Modified
27 June 2011
General Comment
2011-02-08 Scopolamine is an antimuscarinic tropane alkaloid found in the Solanaceae (nightshade) family of plants and first isolated in 1880. The butyl bromide, methobromide and other quaternary ammonium salts are used in conditions associated with visceral spasms. In addition, the methobromide has been used in the prevention of motion sickness and as an adjunct in the treatment of peptic ulcer disease by reducing stomach acid secretion.