CHEBI:16684 - atropine

ChEBI IDCHEBI:16684
ChEBI Nameatropine
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:2917, CHEBI:13866, CHEBI:22674, CHEBI:24754
Last Modified6 March 2020
DownloadsMolfile
FormulaC17H23NO3
Net Charge0
Average Mass289.375
Monoisotopic Mass289.16779
SMILESCN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(CO)c1ccccc1)C2
InChIInChI=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?
InChIKeyRKUNBYITZUJHSG-SPUOUPEWSA-N
Species of MetaboliteComponentSourceComments
Datura stramonium (ncbitaxon:4076) - PubMed (15374592)
Roles Classification
Biological Roles:
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.
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Applications:
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.
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.
muscarinic antagonist  A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
antidote to sarin poisoning  A role borne by a molecule that acts to counteract or neutralise the nerve agent sarin.
antidote to organophosphate poisoning  A role borne by a molecule that acts to counteract or neutralise the deleterious effects of organophosphates or acetylcholinesterase inhibitors (nerve agents).
oneirogen  Any substance that produces or enhances dream-like states of consciousness.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
bronchodilator agent  An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
hyperglycemic agent  A drug which increases the blood glucose level.
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.
vasoconstrictor agent  Drug used to cause constriction of the blood vessels.
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.
antidote  Any protective agent counteracting or neutralizing the action of poisons.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
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 analgesic (CHEBI:35480)
atropine (CHEBI:16684) has role anti-arrhythmia drug (CHEBI:38070)
atropine (CHEBI:16684) has role antibacterial agent (CHEBI:33282)
atropine (CHEBI:16684) has role antidote (CHEBI:50247)
atropine (CHEBI:16684) has role antidote to organophosphate poisoning (CHEBI:90753)
atropine (CHEBI:16684) has role antidote to sarin poisoning (CHEBI:136860)
atropine (CHEBI:16684) has role antineoplastic agent (CHEBI:35610)
atropine (CHEBI:16684) has role bronchodilator agent (CHEBI:35523)
atropine (CHEBI:16684) has role cardiovascular drug (CHEBI:35554)
atropine (CHEBI:16684) has role hyperglycemic agent (CHEBI:76916)
atropine (CHEBI:16684) has role insulin-sensitizing drug (CHEBI:50864)
atropine (CHEBI:16684) has role muscarinic antagonist (CHEBI:48876)
atropine (CHEBI:16684) has role mydriatic agent (CHEBI:50513)
atropine (CHEBI:16684) has role oneirogen (CHEBI:146270)
atropine (CHEBI:16684) has role ophthalmology drug (CHEBI:66981)
atropine (CHEBI:16684) has role parasympatholytic (CHEBI:50370)
atropine (CHEBI:16684) has role plant metabolite (CHEBI:76924)
atropine (CHEBI:16684) has role vasoconstrictor agent (CHEBI:50514)
atropine (CHEBI:16684) is a racemate (CHEBI:60911)
Incoming Relation(s)
(6S)-6-hydroxyhyoscyamine (CHEBI:15645) has functional parent atropine (CHEBI:16684)
atropine sulfate (CHEBI:233047) 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  Source
[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoateIUPHAR
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateChEBI
8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropateNIST Chemistry WebBook
AtropinChemIDplus
atropinaChEBI
Brand Names  Source
AtrojectChEMBL
AtropenChEMBL
AtrophateChEMBL
Atropine (autoinjector)ChEMBL
Atropine component of atnaaChEMBL
Atropine component of duodoteChEMBL
Manual XrefsDatabases
C01479KEGG COMPOUND
D00113KEGG DRUG
DB00572DrugBank
HMDB0014712HMDB
Registry NumbersSources
Reaxys:1545928Reaxys
Beilstein:4236545Beilstein
CAS:51-55-8ChemIDplus
CAS:51-55-8KEGG COMPOUND
CAS:51-55-8NIST Chemistry WebBook
Citations