EPINEPHRINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC A01AD01 B02BC09 C01CA24 R01AA14 R03AA01 S01EA01
UNII YKH834O4BH
EPA CompTox DTXSID5022986

Structure

InChI Key UCTWMZQNUQWSLP-VIFPVBQESA-N
Smiles CNC[C@H](O)c1ccc(O)c(O)c1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C9H13NO3
Molecular Weight 183.21
AlogP 0.35
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 3.0
Polar Surface Area 72.72
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 13.0

Bioactivity

Mechanism of Action Action Reference
Adrenergic receptor agonist AGONIST DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
15-436 17 630-631 200-14000 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - 55000 910 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 29
Assay Description Organism Bioactivity Reference
Displacement of [3H]clonidine from adrenergic alpha 2 receptor of rat cerebral cortical membranes Rattus norvegicus 38.0 nM
Binding affinity against adrenergic beta 2 receptor versus 1 nM [3H]dihydroalprenolol in rat cerebral cerebellar membranes None 720.0 nM
Binding affinity against Alpha adrenergic receptor using [3H]dihydroergocryptine radioligand in rat brain homogenate None 17.0 nM
Agonistic potency at alpha-1 adrenergic receptor for the amine-induced increase of phosphatidylinositol breakdown in synaptoneurosomes from guinea pig cerebral cortex Cavia porcellus 400.0 nM
Binding affinity against alpha 2-Adrenergic receptor in guinea pig cerebral cortical membranes by displacement of [3H]clonidine Cavia porcellus 5.0 nM
Inhibition of [3H]p-aminoclonidine (PAC) binding to alpha-2 adrenergic receptor of purified human platelet plasma membranes None 8.0 nM
Agonistic potency at alpha 2-Adrenergic receptor for inhibition of 10 uM forskolin-elicited stimulation of adenylate cyclase in human platelet membranes Homo sapiens 300.0 nM
Compound was evaluated for inhibition of [3H]prazosin binding to Alpha-1 adrenergic receptor in rat forebrain homogenate. None 200.0 nM
Effective dose for relaxation of guinea pig trachea. Cavia porcellus 15.0 nM Effective dose for relaxation of guinea pig trachea. Cavia porcellus 436.0 nM
Binding of [3H]dihydroalprenolol to beta-2 adrenergic receptor of rat cerebral cortical membranes None 660.0 nM
Agonistic potency at beta adrenergic receptor for the stimulation of accumulation of cyclic AMP in cultured C6 glioma cells None 230.0 nM
Agonistic potency at beta-1 adrenergic receptor for the percent maximal increase in contraction rate of isolated guinea pig atria Cavia porcellus 260.0 nM
Effective dose required to stimulate contractions in isolated guinea pig atrium. Cavia porcellus 15.0 nM Effective dose required to stimulate contractions in isolated guinea pig atrium. Cavia porcellus 436.0 nM
Stimulation of cyclic AMP accumulation in C6 glioma cells expressing adrenergic beta receptor Rattus norvegicus 230.0 nM
Effective concentration for stimulation of [3H]phosphoinositide formation in guinea pig synaptoneurosomes expressing alpha-1 receptor Cavia porcellus 400.0 nM
Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical membranes None 13.0 nM Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical membranes None 15.0 nM
Agonist activity at human adrenergic beta-3 receptor expressed in CHO cells assessed as cAMP levels by DELFIA method Homo sapiens 31.0 nM
Agonist activity at human adrenergic beta3 receptor expressed in CHO cells assessed as [3H]cAMP levels by radiolabeled ligand based assay Homo sapiens 49.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 29.1 %
Displacement of radioligand from rat alpha2 adrenergic receptor by liquid scintillation spectrometry Rattus norvegicus 160.0 nM
Binding affinity to human adrenergic beta2 receptor Homo sapiens 630.0 nM
Binding affinity to human beta-2 adrenergic receptor delta 5-C271 mutant expressed in Spodoptera frugiperda Sf9 cells Homo sapiens 110.0 nM
Binding affinity to human beta-2 adrenergic receptor delta 5-C271/W135 mutant expressed in Spodoptera frugiperda Sf9 cells Homo sapiens 100.0 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 628.0 nM DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 254.0 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 977.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 449.0 nM DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 221.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 737.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 276.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 869.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 397.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 356.0 nM
DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 284.0 nM DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) None 196.0 nM
DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 232.0 nM DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) Rattus norvegicus 154.0 nM
Binding affinity to beta-2 adrenergic receptor (unknown origin) at 1 to 10000 nM Homo sapiens 630.96 nM
Displacement of [3H]CGP12177 from human beta2 receptor expressed in CHO cells Homo sapiens 360.0 nM
Displacement of [3H]spiperone from human D2S receptor expressed in CHO cells Homo sapiens 910.0 nM
Displacement of [3H]RS-79948-197 from recombinant human alpha2A adrenoreceptor expressed in CHOK1 cell membrane by scintillation counting method Homo sapiens 160.0 nM
Agonist activity at recombinant human alpha2A adrenoreceptor expressed in CHOK1 cell membrane incubated for 30 mins by [35S]GTPgammaS binding assay Homo sapiens 30.2 nM
Agonist activity at human beta1 adrenergic receptor expressed in CHOK1 cells co-expressing Galpha15 assessed as increase in calcium influx by measuring fluorescence intensity by FLIPR assay Homo sapiens 290.0 nM
Agonist activity at human alpha1 beta adrenergic receptor expressed in CHOK1 cells co-expressing Galpha15 assessed as increase in calcium influx by measuring fluorescence intensity by FLIPR assay Homo sapiens 75.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -34.41 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.07 %

Related Entries

Cross References

Resources Reference
ChEBI 28918
ChEMBL CHEMBL679
DrugBank DB00668
DrugCentral 1028
FDA SRS YKH834O4BH
Human Metabolome Database HMDB0000068
Guide to Pharmacology 479
KEGG C00788
PDB ALE
PharmGKB PA449470
PubChem 5816
SureChEMBL SCHEMBL3814
ZINC ZINC000000039089
CONTENTS