ephedrine   Click here for help

GtoPdb Ligand ID: 556

Synonyms: Emerphed® (ephedrine sulfate injection)
Approved drug
ephedrine is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: Ephedrine is a sympathomimetic amine, hypothesised to act principally as a β-adrenoceptor agonist. Natural ephedrine is used in Chinese traditional medicine as a treatment for asthma and bronchitis.
Chemically, ephedirine can exist as four stereoisomers: the (1R,2S) and (1S,2R) pair of enantiomers is known as ephedrine ( with the INN racephedrine aknowledging the racemic mixture), while (1R,2R) and (1S,2S) pair is known as pseudoephedrine. The (1R,2S) isomer is also named (-)-ephedrine or D-ephedrine. The (1S,2S) isomer being (+)-ephedrine or L-ephedrine. Pseudoephedrine is much less active than ephedrine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 32.26
Molecular weight 165.12
XLogP 1.39
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(C(c1ccccc1)O)C
Isomeric SMILES CN[C@H]([C@@H](c1ccccc1)O)C
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
InChI Key KWGRBVOPPLSCSI-WPRPVWTQSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(1R,2S)-2-methylamino-1-phenylpropan-1-ol
International Nonproprietary Names Click here for help
INN number INN
6626 racephedrine
Synonyms Click here for help
Emerphed® (ephedrine sulfate injection)
Database Links Click here for help
CAS Registry No. 299-42-3 (source: DrugBank)
ChEBI CHEBI:15407
ChEMBL Ligand CHEMBL211456
DrugBank Ligand DB01364
DrugCentral Ligand 1024
GtoPdb PubChem SID 135650234
PubChem CID 9294
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Wikipedia Ephedrine