Services
Research
Training
Industry
About us
ChEBI
Examples:
iron*
,
InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
Advanced
Home
Advanced Search
Browse
Documentation
Download
Tools
About ChEBI
Submit
Contact us
DiNA
Statistics
Entity of the Month
Periodic Table
Ontology
Train online
User Manual
Annotation Manual
Developer Manual
FAQ's
BiNChE
libChEBI
Web Services
ChEBI
> Main
CHEBI:80680 - (−)-norephedrine
Main
ChEBI Ontology
Automatic Xrefs
Reactions
Pathways
Models
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 1
R
,2
S
-stereoisomer). It is a plant alkaloid.
Stars
This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download
Molfile
XML
SDF
Find compounds which contain this structure
Find compounds which resemble this structure
Take structure to the Advanced Search
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 (Br
o
nsted 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
(1
R
,2
S
)-2-amino-1-phenylpropan-1-ol
Synonyms
Sources
(−)-norephedrin
ChemIDplus
(1
R
,2
S
)-(−)-norephedrine
ChemIDplus
(1
R
,2
S
)-2-amino-1-phenyl-1-propanol
ChemIDplus
(1
R
,2
S
)-norephedrine
ChemIDplus
(
R
,
S
)-(−)-norephedrine
ChemIDplus
erythro
-(1
R
,2
S
)-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
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