CHEBI:16684 - atropine

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ChEBI Name atropine
ChEBI ID CHEBI:16684
Definition A racemate composed of equimolar concentrations of (S)- and (R)-atropine . It is obtained from deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2917, CHEBI:13866, CHEBI:22674, CHEBI:24754
Supplier Information
Download Molfile XML SDF
Formula C17H23NO3
Net Charge 0
Average Mass 289.36946
Monoisotopic Mass 289.168
InChI InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
InChIKey RKUNBYITZUJHSG-SPUOUPEWSA-N
SMILES CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)c1ccccc1
Metabolite of Species Details
Datura stramonium (NCBI:4076) See: PubMed
Roles Classification
Biological Role(s): 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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
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.
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.
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.
bronchodilator agent
An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
antidote to sarin poisoning
A role borne by a molecule that acts to counteract or neutralise the nerve agent sarin.
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 atropine (CHEBI:16684) has part (R)-atropine (CHEBI:48882)
atropine (CHEBI:16684) has part (S)-atropine (CHEBI:17486)
atropine (CHEBI:16684) has role anaesthesia adjuvant (CHEBI:60807)
atropine (CHEBI:16684) has role anti-arrhythmia drug (CHEBI:38070)
atropine (CHEBI:16684) has role antidote to sarin poisoning (CHEBI:136860)
atropine (CHEBI:16684) has role bronchodilator agent (CHEBI:35523)
atropine (CHEBI:16684) has role muscarinic antagonist (CHEBI:48876)
atropine (CHEBI:16684) has role mydriatic agent (CHEBI:50513)
atropine (CHEBI:16684) has role parasympatholytic (CHEBI:50370)
atropine (CHEBI:16684) has role plant metabolite (CHEBI:76924)
atropine (CHEBI:16684) is a racemate (CHEBI:60911)
Incoming (6S)-6-hydroxyhyoscyamine (CHEBI:15645) has functional parent atropine (CHEBI:16684)
hyoscyamine sulfate dihydrate (CHEBI:28486) has functional parent atropine (CHEBI:16684)
IUPAC Names
rac-(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate
rac-tropan-3α-yl 3-hydroxy-2-phenylpropanoate
Synonyms Sources
(±)-atropine NIST Chemistry WebBook
(±)-hyoscyamine NIST Chemistry WebBook
(+,−)-tropyl tropate ChemIDplus
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropate ChEBI
8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate ChEBI
8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropate NIST Chemistry WebBook
[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoate IUPHAR
Atropin ChemIDplus
atropina ChEBI
Atropine KEGG COMPOUND
dl-Hyoscyamine KEGG COMPOUND
dl-tropyltropate ChemIDplus
tropine tropate ChemIDplus
Database Links Databases
C01479 KEGG COMPOUND
D00113 KEGG DRUG
DB00572 DrugBank
HMDB0014712 HMDB
View more database links
Registry Numbers Types Sources
1545928 Reaxys Registry Number Reaxys
1545928 Beilstein Registry Number Beilstein
4236545 Beilstein Registry Number Beilstein
51-55-8 CAS Registry Number ChemIDplus
51-55-8 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
15374592 PubMed citation Europe PMC
18369575 PubMed citation Europe PMC
Last Modified
20 April 2017