(±)-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
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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
Classification Click here for help
Compound class Metabolite or derivative
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.
Prodrug dipivefrine
IUPAC Name Click here for help
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
Specialist databases
GPCRdb Ligand (plusmn)-adrenaline
Other databases
BindingDB Ligand 50019058
CAS Registry No. 329-65-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1740
DrugCentral Ligand 4508
GtoPdb PubChem SID 135651547
PubChem CID 838
Search Google for chemical match using the InChIKey UCTWMZQNUQWSLP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UCTWMZQNUQWSLP
Search PubMed clinical trials racepinefrine
Search PubMed titles racepinefrine
Search PubMed titles/abstracts racepinefrine
UniChem Compound Search for chemical match using the InChIKey UCTWMZQNUQWSLP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UCTWMZQNUQWSLP-UHFFFAOYSA-N
Wikipedia Epinephrine