(-)-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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: adrenaline

2D Structure
Click here for structure editor
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
Natural/Endogenous Targets
Target
α1A-adrenoceptor
α1B-adrenoceptor
α1D-adrenoceptor
α2A-adrenoceptor
α2B-adrenoceptor
α2C-adrenoceptor
β1-adrenoceptor
β2-adrenoceptor
β3-adrenoceptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Monoamine oxidase A
Phenylethanolamine N-methyltransferase
Monoamine oxidase B
Catechol-O-methyltransferase
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Vesicular monoamine transporter 1 1
Vesicular monoamine transporter 2 1
DAT
NET
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
α1D-adrenoceptor Hs Agonist Full agonist 7.2 pKi - 4,9
pKi 7.2 [4,9]
α2A-adrenoceptor Hs Agonist Full agonist 5.8 – 7.4 pKi - 6,8
pKi 5.8 – 7.4 [6,8]
α1B-adrenoceptor Hs Agonist Full agonist 6.5 pKi - 9
pKi 6.5 [9]
α1A-adrenoceptor Hs Agonist Full agonist 6.3 – 6.5 pKi - 4,9
pKi 6.3 – 6.5 [4,9]
α1D-adrenoceptor Rn Agonist Full agonist 6.3 pKi - 7
pKi 6.3 [7]
β2-adrenoceptor Hs Agonist Full agonist 6.0 – 6.2 pKi - 2-3,5
pKi 6.0 – 6.2 [2-3,5]
α2C-adrenoceptor Hs Agonist Agonist 5.8 pKi - 6
pKi 5.8 [6]
β1-adrenoceptor Hs Agonist Agonist 5.4 – 6.0 pKi - 2-3
pKi 5.4 – 6.0 [2-3]
α2B-adrenoceptor Hs Agonist Agonist 5.2 pKi - 6
pKi 5.2 [6]
β3-adrenoceptor Hs Agonist Agonist 3.9 pKi - 3
pKi 3.9 [3]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
carbonic anhydrase 1 Hs Activator Activation - - - 10
KA 90 nM [10]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Ligand mentioned in the following text fields