CHEBI:61272 - scopolamine hydrobromide trihydrate

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ChEBI Name scopolamine hydrobromide trihydrate
ChEBI ID CHEBI:61272
Definition A hydrate that is the trihydrate form of scopolamine hydrobromide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H28BrNO7
Net Charge 0
Average Mass 438.31100
Monoisotopic Mass 437.10492
InChI InChI=1S/C17H21NO4.BrH.3H2O/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10;;;;/h2-6,11-16,19H,7-9H2,1H3;1H;3*1H2/t11-,12-,13-,14+,15-,16+;;;;/m1..../s1
InChIKey LACQPOBCQQPVIT-SEYKEWMNSA-N
SMILES O.O.O.Br.CN1[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.
Application(s): 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.
mydriatic agent
Agent that dilates the pupil. Used in eye diseases and to facilitate eye examination. It may be either a sympathomimetic or parasympatholytic. The latter cause cycloplegia or paralysis of accommodation at high doses and may precipitate glaucoma.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
anaesthesia adjuvant
Any substance that possesses little anaesthetic effect by itself, but which enhances or potentiates the anaesthetic action of other drugs when given at the same time.
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.
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ChEBI Ontology
Outgoing scopolamine hydrobromide trihydrate (CHEBI:61272) has part scopolamine hydrobromide (anhydrous) (CHEBI:61271)
scopolamine hydrobromide trihydrate (CHEBI:61272) has role anaesthesia adjuvant (CHEBI:60807)
scopolamine hydrobromide trihydrate (CHEBI:61272) has role antiemetic (CHEBI:50919)
scopolamine hydrobromide trihydrate (CHEBI:61272) has role antispasmodic drug (CHEBI:53784)
scopolamine hydrobromide trihydrate (CHEBI:61272) has role muscarinic antagonist (CHEBI:48876)
scopolamine hydrobromide trihydrate (CHEBI:61272) has role mydriatic agent (CHEBI:50513)
scopolamine hydrobromide trihydrate (CHEBI:61272) is a hydrate (CHEBI:35505)
IUPAC Names
(1R,2R,4S,5S,7s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrobromide—water (1/3)
(1R,2R,4S,5S,7s,9s)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9-methyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane bromide—water (1/3)
Synonyms Sources
(−)-scopolamine hydrobromide trihydrate ChemIDplus
hyoscine hydrobromide trihydrate ChemIDplus
scopolamine hydrobromide
Note: (2011-02-08) Note that the name scopolamine hydrobromide is also used to refer to anhydrous scopolamine hydrobromide.
ChemIDplus
scopolaminium bromide trihydrate ChEBI
scopolammonium bromide trihydrate ChEBI
Brand Names Sources
Hysco KEGG DRUG
Isopto hyoscine KEGG DRUG
Manual Xrefs Databases
D02071 KEGG DRUG
DB00747 DrugBank
View more database links
Registry Numbers Types Sources
6533-68-2 CAS Registry Number ChemIDplus
6533-68-2 CAS Registry Number KEGG DRUG
Last Modified
27 June 2011
General Comment
2011-02-08 Scopolamine is a tropane alkaloid found in the Solanaceae (nightshade) family of plants and first isolated in 1880. An antimuscarinic, scopolamine and its hydrobromide trihydrate salt are used for the prevention of motion sickness and of postoperative nausea and vomiting. The hydrobromide trihydrate is also used for eye disorders as a mydriatic (it has a faster onset and shorter duration of action than atropine) and as an antispasmodics to relieve the pain of smooth muscle spasm associated with the gastrointestinal tract.