CHEBI:8093 - phenylephrine

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ChEBI Name phenylephrine
ChEBI ID CHEBI:8093
Definition A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C9H13NO2
Net Charge 0
Average Mass 167.20500
Monoisotopic Mass 167.095
InChI InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChIKey SONNWYBIRXJNDC-VIFPVBQESA-N
SMILES CNC[C@H](O)c1cccc(O)c1
Roles Classification
Biological Role(s): sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
Application(s): cardiotonic drug
A drug that has a strengthening effect on the heart or that can increase cardiac output.
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.
protective agent
Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
nasal decongestant
A drug used to relieve nasal congestion in the upper respiratory tract.
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing phenylephrine (CHEBI:8093) has role α-adrenergic agonist (CHEBI:35569)
phenylephrine (CHEBI:8093) has role cardiotonic drug (CHEBI:38147)
phenylephrine (CHEBI:8093) has role mydriatic agent (CHEBI:50513)
phenylephrine (CHEBI:8093) has role nasal decongestant (CHEBI:77715)
phenylephrine (CHEBI:8093) has role protective agent (CHEBI:50267)
phenylephrine (CHEBI:8093) has role sympathomimetic agent (CHEBI:35524)
phenylephrine (CHEBI:8093) has role vasoconstrictor agent (CHEBI:50514)
phenylephrine (CHEBI:8093) is a phenols (CHEBI:33853)
phenylephrine (CHEBI:8093) is a phenylethanolamines (CHEBI:25990)
phenylephrine (CHEBI:8093) is a secondary amino compound (CHEBI:50995)
phenylephrine (CHEBI:8093) is conjugate base of phenylephrine(1+) (CHEBI:132294)
Incoming phenylephrine(1+) (CHEBI:132294) is conjugate acid of phenylephrine (CHEBI:8093)
IUPAC Name
3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
INNs Sources
fenilefrina ChemIDplus
phenylephrine ChemIDplus
phenylephrinum ChemIDplus
Synonyms Sources
(−)-m-hydroxy-α-(methylaminomethyl)benzyl alcohol NIST Chemistry WebBook
Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (R)- NIST Chemistry WebBook
Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)- ChemIDplus
Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)- ChemIDplus
l-(3-Hydroxyphenyl)-N-methylethanolamine NIST Chemistry WebBook
Phenylephrine KEGG COMPOUND
R(-)-Phenylephrine ChemIDplus
Database Links Databases
2146 DrugCentral
C07441 KEGG COMPOUND
D08365 KEGG DRUG
DB00388 DrugBank
HMDB0002182 HMDB
LSM-15380 LINCS
Phenylephrine Wikipedia
US1932347 Patent
US1954389 Patent
View more database links
Registry Numbers Types Sources
3198815 Reaxys Registry Number Reaxys
59-42-7 CAS Registry Number ChemIDplus
59-42-7 CAS Registry Number NIST Chemistry WebBook
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Last Modified
19 June 2017