CHEBI:80680 - (−)-norephedrine

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ChEBI Name (−)-norephedrine
ChEBI ID CHEBI:80680
ChEBI ASCII Name (-)-norephedrine
Definition An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C9H13NO
Net Charge 0
Average Mass 151.209
Monoisotopic Mass 151.09971
InChI InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
InChIKey DLNKOYKMWOXYQA-CBAPKCEASA-N
SMILES C[C@H](N)[C@H](O)C1=CC=CC=C1
Metabolite of Species Details
Catha edulis (NCBI:txid123405) See: PubMed
Ephedra sinica (NCBI:txid33152) See: PubMed
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): 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.
(via alkaloid )
Application(s): central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
(via amphetamines )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-norephedrine (CHEBI:80680) has role plant metabolite (CHEBI:76924)
(−)-norephedrine (CHEBI:80680) is a amphetamines (CHEBI:35338)
(−)-norephedrine (CHEBI:80680) is a phenethylamine alkaloid (CHEBI:38605)
IUPAC Name
(1R,2S)-2-amino-1-phenylpropan-1-ol
Synonyms Sources
(−)-norephedrin ChemIDplus
(1R,2S)-(−)-norephedrine ChemIDplus
(1R,2S)-2-amino-1-phenyl-1-propanol ChemIDplus
(1R,2S)-norephedrine ChemIDplus
(R,S)-(−)-norephedrine ChemIDplus
erythro-(1R,2S)-norephedrine ChemIDplus
L-(−)-norephedrine ChEBI
l-norephedrine ChemIDplus
l-phenylpropanolamine ChemIDplus
Manual Xrefs Databases
9875 ChemSpider
C00055789 KNApSAcK
C16719 KEGG COMPOUND
EP2055379 Patent
HMDB0243518 HMDB
WO0039071 Patent
View more database links
Registry Numbers Types Sources
2207678 Reaxys Registry Number Reaxys
492-41-1 CAS Registry Number ChemIDplus
492-41-1 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
14750795 PubMed citation Europe PMC
1639915 PubMed citation Europe PMC
20417943 PubMed citation Europe PMC
21924876 PubMed citation Europe PMC
22215969 PubMed citation Europe PMC
22495440 PubMed citation Europe PMC
22727117 PubMed citation Europe PMC
2320655 PubMed citation Europe PMC
23763204 PubMed citation Europe PMC
24818692 PubMed citation Europe PMC
25272887 PubMed citation Europe PMC
26531856 PubMed citation Europe PMC
32589765 PubMed citation Europe PMC
33357002 PubMed citation Europe PMC
8221134 PubMed citation Europe PMC
Last Modified
06 April 2022