(±)-adrenaline   

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.
2D Structure
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Physico-chemical Properties
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
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
Compound class Metabolite or derivative
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Prodrug dipivefrine
IUPAC Name
4-(1-hydroxy-2-methylaminoethyl)benzene-1,2-diol
International Nonproprietary Names
INN number INN
4553 racepinefrine
Synonyms
adrenaline | epinephrine
Database Links
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