CHEBI:15407 - (−)-ephedrine

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ChEBI Name (−)-ephedrine
ChEBI ID CHEBI:15407
ChEBI ASCII Name (-)-ephedrine
Definition A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4801, CHEBI:10776, CHEBI:18483, CHEBI:132176
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Formulae C10H15NO
C10H15NO
Net Charge 0
Average Mass 165.23220
Monoisotopic Mass 165.115
InChI InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
InChIKey KWGRBVOPPLSCSI-WPRPVWTQSA-N
SMILES CN[C@@H](C)[C@H](O)c1ccccc1
Metabolite of Species Details
Pseudomonas putida DOT-T1E (NCBI:1196325) See: MetaboLights Study
Ephedra equisetina (NCBI:173280) See: PubMed
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(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.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
nasal decongestant
A drug used to relieve nasal congestion in the upper respiratory tract.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-ephedrine (CHEBI:15407) has role bacterial metabolite (CHEBI:76969)
(−)-ephedrine (CHEBI:15407) has role environmental contaminant (CHEBI:78298)
(−)-ephedrine (CHEBI:15407) has role nasal decongestant (CHEBI:77715)
(−)-ephedrine (CHEBI:15407) has role plant metabolite (CHEBI:76924)
(−)-ephedrine (CHEBI:15407) has role sympathomimetic agent (CHEBI:35524)
(−)-ephedrine (CHEBI:15407) has role vasoconstrictor agent (CHEBI:50514)
(−)-ephedrine (CHEBI:15407) has role xenobiotic (CHEBI:35703)
(−)-ephedrine (CHEBI:15407) is a phenethylamine alkaloid (CHEBI:38605)
(−)-ephedrine (CHEBI:15407) is a phenylethanolamines (CHEBI:25990)
(−)-ephedrine (CHEBI:15407) is conjugate base of (−)-ephedrinium (CHEBI:57295)
Incoming (−)-ephedrinium (CHEBI:57295) is conjugate acid of (−)-ephedrine (CHEBI:15407)
IUPAC Name
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
Synonyms Sources
(-)-Ephedrine KEGG COMPOUND
(1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane ChEBI
Ephedrine KEGG COMPOUND
L(−)-ephedrine ChemIDplus
L-Ephedrine KEGG COMPOUND
l-ephedrine ChemIDplus
L-erythro-2-(methylamino)-1-phenylpropan-1-ol NIST Chemistry WebBook
Database Links Databases
1024 DrugCentral
4856 Chemspider accession
C00001409 KNApSAcK
C01575 KEGG COMPOUND
D00124 KEGG DRUG
DB01364 DrugBank
Ephedrine Wikipedia
View more database links
Registry Numbers Types Sources
2208730 Reaxys Registry Number Reaxys
261389 Gmelin Registry Number Gmelin
299-42-3 CAS Registry Number ChemIDplus
299-42-3 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
13359219 PubMed citation Europe PMC
13809594 PubMed citation Europe PMC
21465337 PubMed citation Europe PMC
25660335 PubMed citation Europe PMC
27662264 PubMed citation Europe PMC
27846433 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag