cyclopentolate (CHEBI:4024)

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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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C17H25NO3

Net Charge

Average Mass

291.38530

Monoisotopic Mass

291.18344

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.

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

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

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.