CHEBI:4024 - cyclopentolate

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ChEBI Name cyclopentolate
ChEBI ID CHEBI:4024
Definition A carboxylic ester resulting from the formal condensation of (1-hydroxycyclopentyl)(phenyl)acetic acid with N,N-dimethylethanolamine. A tertiary amine antimuscarinic with actions similar to atropine, it is used as its hydrochloride salt to produce mydriasis (excessive dilation of the pupil) and cycloplegia (paralysis of the ciliary muscle of the eye) for opthalmic diagnostic procedures. It acts more quickly than atropine and has a shorter duration of action.
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Formula C17H25NO3
Net Charge 0
Average Mass 291.38530
Monoisotopic Mass 291.183
InChI InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
InChIKey SKYSRIRYMSLOIN-UHFFFAOYSA-N
SMILES CN(C)CCOC(=O)C(c1ccccc1)C1(O)CCCC1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
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): 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
diagnostic agent
A substance administered to aid diagnosis of a disease.
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ChEBI Ontology
Outgoing cyclopentolate (CHEBI:4024) has functional parent (1-hydroxycyclopentyl)phenylacetic acid (CHEBI:59684)
cyclopentolate (CHEBI:4024) has functional parent N,N-dimethylethanolamine (CHEBI:271436)
cyclopentolate (CHEBI:4024) has role diagnostic agent (CHEBI:33295)
cyclopentolate (CHEBI:4024) has role muscarinic antagonist (CHEBI:48876)
cyclopentolate (CHEBI:4024) has role mydriatic agent (CHEBI:50513)
cyclopentolate (CHEBI:4024) has role parasympatholytic (CHEBI:50370)
cyclopentolate (CHEBI:4024) is a carboxylic ester (CHEBI:33308)
cyclopentolate (CHEBI:4024) is a tertiary alcohol (CHEBI:26878)
cyclopentolate (CHEBI:4024) is a tertiary amino compound (CHEBI:50996)
Incoming cyclopentolate hydrochloride (CHEBI:4025) has part cyclopentolate (CHEBI:4024)
(R)-cyclopentolate (CHEBI:59688) is a cyclopentolate (CHEBI:4024)
(S)-cyclopentolate (CHEBI:59689) is a cyclopentolate (CHEBI:4024)
IUPAC Name
2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate
INNs Sources
ciclopentolato ChemIDplus
cyclopentolate WHO MedNet
cyclopentolate ChemIDplus
cyclopentolatum ChemIDplus
Synonyms Sources
(±)-cyclopentolate ChEBI
1-hydroxy-α-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl ester ChEBI
2-(dimethylamino)ethyl 1-hydroxy-α-phenylcyclopentaneacetate ChemIDplus
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate ChEBI
2-phenyl-2-(1-hydroxycyclopentyl)ethanoic acid β-(dimethylamino)ethyl ester ChEBI
α-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl ester ChEBI
β-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetate NIST Chemistry WebBook
β-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate ChEBI
Cyclopentolate KEGG COMPOUND
Manual Xrefs Databases
757 DrugCentral
C06932 KEGG COMPOUND
Cyclopentolate Wikipedia
D07759 KEGG DRUG
DB00979 DrugBank
HMDB0015114 HMDB
LSM-1800 LINCS
US2554511 Patent
View more database links
Registry Numbers Types Sources
2147087 Beilstein Registry Number Beilstein
2147087 Reaxys Registry Number Reaxys
512-15-2 CAS Registry Number NIST Chemistry WebBook
512-15-2 CAS Registry Number ChemIDplus
Last Modified
22 February 2017
General Comment
2014-05-01 Cyclopentolate can be found in blood and urine samples of individuals who have taken this drug.