ephedrine   

GtoPdb Ligand ID: 556

Synonyms: Emerphed® (ephedrine sulfate injection)
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.
2D Structure
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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
SMILES / InChI / InChIKey
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
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
(1R,2S)-2-methylamino-1-phenylpropan-1-ol
International Nonproprietary Names
INN number INN
6626 racephedrine
Synonyms
Emerphed® (ephedrine sulfate injection)
Database Links
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