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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
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
Specialist databases
GPCRdb Ligand ephedrine
Other databases
CAS Registry No. 299-42-3 (source: DrugBank)
ChEMBL Ligand CHEMBL211456
DrugBank Ligand DB01364
DrugCentral Ligand 1024
GtoPdb PubChem SID 135650234
PubChem CID 9294
Search Google for chemical match using the InChIKey KWGRBVOPPLSCSI-WPRPVWTQSA-N
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UniChem Compound Search for chemical match using the InChIKey KWGRBVOPPLSCSI-WPRPVWTQSA-N
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Wikipedia Ephedrine