(-)-adrenaline   

GtoPdb Ligand ID: 479

Synonyms: adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
(-)-adrenaline is an approved drug (FDA (no history prior to 1951))
Comment: Agonist at alpha and beta adrenoceptors. In addition to being assigned the INN epinephrine in its own right, (-)-adrenaline is also one of the enantiomers found in the INN-assigned compound (±)-adrenaline.
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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 CNC[C@@H](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/t9-/m0/s1
InChI Key UCTWMZQNUQWSLP-VIFPVBQESA-N
Classification
Compound class Metabolite or derivative
Approved drug? Yes (FDA (no history prior to 1951))
IUPAC Name
4-[(1R)-1-hydroxy-2-methylaminoethyl]benzene-1,2-diol
International Nonproprietary Names
INN number INN
2142 epinephrine
4553 racepinefrine
Synonyms
adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
Database Links
BindingDB Ligand 50029050
CAS Registry No. 51-43-4
ChEBI CHEBI:28918
ChEMBL Ligand CHEMBL679
DrugBank Ligand DB00668
DrugCentral Ligand 1028
GtoPdb PubChem SID 135651430
Immunopaedia Search epinephrine
PubChem CID 5816
RCSB PDB Ligand ALE
Search Google for chemical match using the InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
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Search PubMed clinical trials racepinefrine
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Search PubMed titles/abstracts racepinefrine
Search UniChem for chemical match using the InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
Search UniChem for chemicals with the same backbone UCTWMZQNUQWSLP
SynPHARM 1862 (in complex with β2-adrenoceptor)
Wikipedia Epinephrine