(±)-adrenaline   Click here for help

GtoPdb Ligand ID: 509

Synonyms: adrenaline | epinephrine
Comment: The preparation of adrenaline/epinephrine assigned the INN racepinefrine is an racemic mixture of the enantiomers (+)-adrenaline and (-)-adrenaline. The structure shown here does not specify stereochemistry and represents the mixture.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 72.72
Molecular weight 183.09
XLogP 0.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNCC(c1ccc(c(c1)O)O)O
Isomeric SMILES CNCC(c1ccc(c(c1)O)O)O
InChI InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3
InChI Key UCTWMZQNUQWSLP-UHFFFAOYSA-N
Classification Click here for help
Compound class Metabolite or derivative
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Prodrug dipivefrine
IUPAC Name Click here for help
4-(1-hydroxy-2-methylaminoethyl)benzene-1,2-diol
International Nonproprietary Names Click here for help
INN number INN
4553 racepinefrine
Synonyms Click here for help
adrenaline | epinephrine
Database Links Click here for help
BindingDB Ligand 50019058
CAS Registry No. 329-65-7 (source: Scifinder)
ChEBI CHEBI:33568
ChEMBL Ligand CHEMBL1740
DrugCentral Ligand 4508
GtoPdb PubChem SID 135651547
PubChem CID 838
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Wikipedia Epinephrine