DESIPRAMINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC N06AA01
UNII TG537D343B
EPA CompTox DTXSID6022896

Structure

InChI Key HCYAFALTSJYZDH-UHFFFAOYSA-N
Smiles CNCCCN1c2ccccc2CCc2ccccc21
InChI
InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H22N2
Molecular Weight 266.39
AlogP 3.53
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 15.27
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 20.0
Assay Description Organism Bioactivity Reference
Displacement of [3H]ketanserin from 5-hydroxytryptamine 2A receptor expressed NIH3T3 cells None 160.0 nM
Compound was tested for its inhibitory activity against 5-hydroxytryptamine receptor Rattus norvegicus 350.0 nM
Compound was tested for its binding affinity towards brain (Hippocampus) Adenylate cyclase Cavia porcellus 350.0 nM
Compound was tested for its binding affinity towards brain (neocortex) Adenylate cyclase Cavia porcellus 320.0 nM
Compound was tested for its inhibitory activity against Alpha-1 adrenergic receptor None 0.25 nM
In vitro competitive binding versus [N-methyl-3H]WIN-35428 in murine kidney cells transfected with cDNA for human dopamine transporter (DAT) None 0.49 nM
Compound tested for its inhibitory activity against Histamine H1 receptor None 0.8 nM
Inhibition of binding of [3H]imipramine to imipramine receptor in rat brain None 130.0 nM
In vitro activity for the ability to inhibit the uptake of Norepinephrine into mouse cortical slices. Mus musculus 70.0 nM
In vitro inhibition of accumulation of (-)-[3H]Norepinephrine (NA) in mouse brain slices None 70.0 nM
Ability to inhibit reuptake of norepinephrine ([3H]NE) at norepinephrine transporter of rat parietal/occipital region None 7.36 nM
Compound was tested for its inhibitory activity against Noradrenaline receptor Rattus norvegicus 2.0 nM
Tested for in vitro reuptake inhibition of [3H]-5-hydroxy tryptamine in pig frontal synaptosomes. Sus scrofa 420.0 nM
Tested for in vitro reuptake inhibition of [3H]norepinephrine in pig occipital synaptosomes. Sus scrofa 3.2 nM
Compound was tested for inhibition of uptake of [14C]5-HT (5-HT) into rat whole brain, in vitro. Rattus norvegicus 11.0 nM
Compound was tested for inhibition of uptake of [14C]norepinephrine (NE) into rat brain hypothalamus, in vitro. Rattus norvegicus 25.0 nM
Inhibition of uptake of tritiated norepinephrine (NE) into rat brain synaptosomes None 150.0 nM
Ability to inhibit the uptake of norepinephrine (NE) by crude synaptosomes from rat whole brain Rattus norvegicus 80.0 nM
Compound was tested in vitro for beta -adrenergic sensitivity and administered to rats at 10 mg/kg, perorally, twice daily for 10 days. Rattus norvegicus -50.0 %
Inhibitory activity of compound against ability of NE to enhance the inhibition produced by GABA after 1 i.p. injection of 10 mg/kg administered (acute treatment) Rattus norvegicus 68.0 %
Inhibitory activity of compound against ability of NE to enhance the inhibition produced by GABA after ip injection of 10 mg/kg administered once a day for 21 days (chronic treatment) Rattus norvegicus 49.0 %
Percent inhibitory activity caused by norepinephrine after 1 i.p. injection of 10 mg/kg administered (acute treatment) Rattus norvegicus 3.5 %
Percent inhibitory activity caused by norepinephrine after ip injection of 10 mg/kg administered once a day for 21 days (chronic treatment) Rattus norvegicus 7.8 %
Inhibition of uptake of tritiated norepinephrine (NE) in rat synaptosomes None 0.65 nM
Inhibition the uptake of tritiated serotonin (5-HT) by the serotonin transporter SERT in rat synaptosomes None 182.0 nM
Ability to inhibit reuptake of serotonin ([3H]5-HT) at serotonin transporter of rat midbrian None 163.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 80.3 %
Inhibitory constant against reuptake of [3H]NE at norepinephrine transporter of rat parietal-occipital cortex Rattus norvegicus 7.36 nM
Inhibitory constant against reuptake of [3H]5-HT at serotonin transporter of rat midbrain cortex Rattus norvegicus 163.0 nM
Binding affinity at NET Homo sapiens 1.0 nM
Inhibition of [3H]serotonin uptake in human wild type SERT transfected HEK293 cells Homo sapiens 108.0 nM
Inhibition of [3H]serotonin uptake in human SERT K490T mutant transfected HEK293 cells Homo sapiens 52.4 nM
Displacement of [3H]DMI from norepinephrine transporter None 580.0 nM
Displacement of [3H]nisoxetine from human norepinephrine transporter expressed in MDCK-Net6 cells Homo sapiens 2.1 nM
Inhibition of norepinephrine uptake at human norepinephrine transporter expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Inhibition of [3H]5HT uptake at human SERT expressed in HEK293 cells Homo sapiens 64.0 nM
Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells Homo sapiens 4.2 nM
Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Inhibition of [3H]NE uptake at human NET EL2 chimera mutant expressed in african green monkey COS1 cells after 48 hrs Homo sapiens 0.7413 nM
Displacement of [125I]RTI-55 from human NET expressed in MDCK cell membrane Homo sapiens 0.93 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 84.3 %
Inhibition of norepinephrine uptake at human NET expressed in MDCK cells Homo sapiens 3.9 nM
Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Antagonist activity at human 5HT3A receptor expressed in HEK293 cells assessed as inhibition of serotonin-induced inward Na+ current at >= 10 uM Homo sapiens 50.0 %
Inhibition of [3H]norepinephrine reuptake at norepinephrine transporter None 5.11 nM
Inhibition of [3H]norepinephrine uptake at human NET expressed in MDCK-Net6 cells by scintillation counting Homo sapiens 3.4 nM
Inhibition of [3H]nisoxetine binding to human NET expressed in MDCK-Net6 cells by plate scintillation counting Homo sapiens 2.1 nM
Inhibition of human NET expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Inhibition of norepinephrine reuptake at human NET expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Inhibition of norepinephrine reuptake at NET None 0.6 nM
Inhibition of norepinephrine uptake at human NET expressed in MDCK-Net6 cells Homo sapiens 3.4 nM
Displacement of [3H]nisoxetine from human NET expressed in MDCK-Net6 cells Homo sapiens 3.3 nM
Inhibition of human NET transfected in MDCK-Net6 cells Homo sapiens 3.4 nM
Inhibition of human NET-mediated norepinephrine uptake in MDCK-Net6 cells Homo sapiens 3.4 nM
Displacement of [3H]nisoxetine from human NET expressed in MDCK-Net6 cells Homo sapiens 2.1 nM
Displacement of [3H]nisoxetine from rat NET in rat cerebral cortex Rattus norvegicus 0.78 nM
Inhibition of human NET Homo sapiens 0.83 nM
Inhibition of SERT None 20.0 nM
Inhibition of human NET expressed in MDCK-Net6 cells assessed as inhibition of norepinephrine uptake Homo sapiens 3.4 nM
Displacement of [3H]nisoxetine from human NET expressed in MDCK-Net6 cells Homo sapiens 2.1 nM
TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation (Calcein-AM: ? uM, Desipramine: 100 uM) in MDR1-expressing MDCKII cells None 12.8 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 25.9 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 3.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens -4.4 %
Inhibition of human SERT expressed in HEK293-MSR cells by 5-HT uptake assay Homo sapiens 560.0 nM
Displacement of [125I]RTI55 from human recombinant norepinephrine transporter expressed in MDCK cells after 3 hrs Homo sapiens 0.92 nM Displacement of [125I]RTI55 from human recombinant norepinephrine transporter expressed in MDCK cells after 3 hrs Homo sapiens 0.93 nM
Displacement of [125I]RTI55 from human recombinant norepinephrine transporter expressed in MDCK cells at 10 uM after 3 hrs relative to control Homo sapiens 49.0 %
Displacement of [3H]Nisoxetine from human recombinant NET over-expressed in dog MDCK cells Homo sapiens 1.5 nM
Displacement of [3H]Nisoxetine from norepinephrine transporter (unknown origin) Homo sapiens 1.148 nM Displacement of [3H]Nisoxetine from norepinephrine transporter (unknown origin) Homo sapiens 1.1 nM
Antidepressant activity in ip dosed NMRI albino mouse assessed as inhibition of [3H]5-HT accumulation in hypothalamus after 0.5 hrs Mus musculus 23.0 %
Antidepressant activity in ip dosed NMRI albino mouse assessed as inhibition of [3H]DA accumulation in hypothalamus after 0.5 hrs Mus musculus 0.0 %
Displacement of [3H]nisoxetine from human NET expressed in HEK293 cells measured after 30 mins Homo sapiens 2.5 nM
Displacement of [3H]nisoxetine from human NET expressed in HEK293 cells at 10 uM measured after 30 mins Homo sapiens 50.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.09 %
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 0.02 % 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 0.02 %
Inhibition of norepinephrine transporter (unknown origin) Homo sapiens 3.917 nM
Displacement of [3H]-Nisoxetine from human NET expressed in HEK cell membrane assessed as inhibition constant by radioligand binding assay Homo sapiens 3.0 nM
Displacement of [3H]-Nisoxetine from human NET expressed in HEK cell membrane at 10 uM by radioligand binding assay relative to control Homo sapiens 50.0 %

Related Entries

Cross References

Resources Reference
ChEBI 47781
ChEMBL CHEMBL72
DrugBank DB01151
DrugCentral 812
FDA SRS TG537D343B
Human Metabolome Database HMDB0015282
Guide to Pharmacology 2399
KEGG C06943
PDB DSM
PharmGKB PA449233
PubChem 2995
SureChEMBL SCHEMBL34384
ZINC ZINC000001530611
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