ephedrine

Ligand id: 556

Name: ephedrine

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(1R,2S)-2-methylamino-1-phenylpropan-1-ol
International Nonproprietary Names
INN number INN
6626 racephedrine
Comments
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.
Database Links
CAS Registry No. 299-42-3 (source: DrugBank)
ChEBI CHEBI:15407
ChEMBL Ligand CHEMBL211456
DrugBank Ligand DB01364
GtoPdb PubChem SID 135650234
PubChem CID 9294
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Wikipedia Ephedrine