CHEBI:15407 - (−)-ephedrine

ChEBI IDCHEBI:15407
ChEBI Name(−)-ephedrine
Stars
ASCII Name(-)-ephedrine
DefinitionA 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.
Secondary ChEBI IDsCHEBI:4801, CHEBI:10776, CHEBI:18483, CHEBI:132176
Last Modified22 February 2017
SubmitterKeeva, Marcus Ennis
DownloadsMolfile
FormulaC10H15NO
Net Charge0
Average Mass165.236
Monoisotopic Mass165.11536
SMILESCN[C@@H](C)[C@H](O)c1ccccc1
InChIInChI=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
InChIKeyKWGRBVOPPLSCSI-WPRPVWTQSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Ephedra equisetina (ncbitaxon:173280) - PubMed (21465337)
Pseudomonas putida DOT-T1E (ncbitaxon:1196325) - MetaboLights (MTBLS319)
Roles Classification
Chemical Roles:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
nasal decongestant  A drug used to relieve nasal congestion in the upper respiratory tract.
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.
ChEBI Ontology
Outgoing Relation(s)
(−)-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 Relation(s)
(−)-ephedrinium (CHEBI:57295) is conjugate acid of (−)-ephedrine (CHEBI:15407)
IUPAC Name 
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
Synonyms  Source
EphedrineKEGG COMPOUND
(-)-EphedrineKEGG COMPOUND
L-EphedrineKEGG COMPOUND
L(−)-ephedrineChemIDplus
L-erythro-2-(methylamino)-1-phenylpropan-1-olNIST Chemistry WebBook
(1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropaneChEBI
Manual XrefsDatabases
C01575KEGG COMPOUND
DB01364DrugBank
EphedrineWikipedia
C00001409KNApSAcK
D00124KEGG DRUG
4856ChemSpider
1024DrugCentral
2959VSDB
Registry NumbersSources
Gmelin:261389Gmelin
Reaxys:2208730Reaxys
CAS:299-42-3KEGG COMPOUND
CAS:299-42-3ChemIDplus
CAS:299-42-3NIST Chemistry WebBook
Citations