CHEBI:16794 - scopolamine

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ChEBI Name scopolamine
ChEBI ID CHEBI:16794
Definition A tropane alkaloid that is the (S)-tropic acid ester of 6β,7β-epoxy-1αH,5αH-tropan-3α-ol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9056, CHEBI:15066, CHEBI:26610
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Formula C17H21NO4
Net Charge 0
Average Mass 303.35290
Monoisotopic Mass 303.147
InChI InChI=1S/C17H21NO4/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/t11-,12-,13-,14+,15-,16+/m1/s1
InChIKey STECJAGHUSJQJN-FWXGHANASA-N
SMILES 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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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): 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.
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.
adjuvant
Any pharmacological or immunological agent that modifies the effect of other agents such as drugs or vaccines while having few if any direct effects when given by itself.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing scopolamine (CHEBI:16794) has functional parent (S)-tropic acid (CHEBI:30766)
scopolamine (CHEBI:16794) has role adjuvant (CHEBI:60809)
scopolamine (CHEBI:16794) has role anaesthesia adjuvant (CHEBI:60807)
scopolamine (CHEBI:16794) has role antidepressant (CHEBI:35469)
scopolamine (CHEBI:16794) has role antiemetic (CHEBI:50919)
scopolamine (CHEBI:16794) has role antispasmodic drug (CHEBI:53784)
scopolamine (CHEBI:16794) has role metabolite (CHEBI:25212)
scopolamine (CHEBI:16794) has role muscarinic antagonist (CHEBI:48876)
scopolamine (CHEBI:16794) has role mydriatic agent (CHEBI:50513)
scopolamine (CHEBI:16794) is a epoxide (CHEBI:32955)
scopolamine (CHEBI:16794) is a propanoate ester (CHEBI:36243)
scopolamine (CHEBI:16794) is a tertiary amino compound (CHEBI:50996)
scopolamine (CHEBI:16794) is a tropane alkaloid (CHEBI:37332)
scopolamine (CHEBI:16794) is conjugate base of scopolamine(1+) (CHEBI:61269)
Incoming scopolamine methobromide (CHEBI:61276) has functional parent scopolamine (CHEBI:16794)
scopolamine(1+) (CHEBI:61269) is conjugate acid of scopolamine (CHEBI:16794)
IUPAC Name
(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (2S)-3-hydroxy-2-phenylpropanoate
Synonyms Sources
(−)-hyoscine ChemIDplus
(−)-scopolamine ChemIDplus
(-)-Hyoscine KEGG COMPOUND
(1S,3S,5R,6R,7S)-6,7-epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate ChEBI
6,7-Epoxytropine tropate ChemIDplus
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate ChemIDplus
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester ChemIDplus
Hyoscine ChemIDplus
scopine (−)-tropate ChemIDplus
Scopolamine KEGG COMPOUND
scopolamine UniProt
Brand Name Source
Transderm-Scop KEGG DRUG
Database Links Databases
C00002292 KNApSAcK
C01851 KEGG COMPOUND
D00138 KEGG DRUG
DB00747 DrugBank
HMDB0003573 HMDB
Scopolamine Wikipedia
SCOPOLAMINE MetaCyc
View more database links
Registry Numbers Types Sources
51-34-3 CAS Registry Number KEGG COMPOUND
51-34-3 CAS Registry Number ChemIDplus
51-34-3 CAS Registry Number NIST Chemistry WebBook
91904 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11718188 PubMed citation Europe PMC
23334071 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-02-07 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, while the butylbromide and other quaternary ammonium derivatives are used as antispasmodics to relieve the pain of smooth muscle spasm associated with the gastrointestinal tract.