Synonyms
Status
Molecule Category Free-form
ATC N04BC02
UNII 24MJ822NZ9
EPA CompTox DTXSID2023438

Structure

InChI Key YEHCICAEULNIGD-MZMPZRCHSA-N
Smiles CCCN1C[C@H](CSC)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21
InChI
InChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,18-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H26N2S
Molecular Weight 314.5
AlogP 4.27
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 19.03
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 22.0
Assay Description Organism Bioactivity Reference
Binding affinity against 5-hydroxytryptamine 1A receptor from bovine hippocampus, used [3H]8-OH-DPAT as radioligand None 1.8 nM
Binding affinity towards Serotonin 5-hydroxytryptamine 1A receptor by displacement of [3H]-(+)-8-OH-DPAT. Homo sapiens 4.0 nM
In vitro affinity for alpha adrenergic receptor by displacement of 3[H]clonidine in calf cerebral cortex Bos taurus 41.0 nM
Alpha-2 adrenergic receptor activity assessed in vitro for displacement of [3H]clonidine from specific binding sites on rat striatal membranes None 41.0 nM
In vitro inhibitory activity against alpha-1 adrenergic receptor from whole rat brain using [3H]WB-4101 as radioligand None 550.0 nM
In vitro inhibitory activity against alpha-2 adrenergic receptor from rat brain minus cerebellum using [3H]clonidine as radioligand None 170.0 nM
Compound was tested for neuronal inhibition of postganglionic cardio accelerator nerve stimulation in anaesthetized cat at 2 Hz frequency at 10 mg/kg Felis catus 59.0 %
Compound was tested for neuronal inhibition of postganglionic cardio accelerator nerve stimulation in anaesthetized cat at 2 Hz frequency at 30 mg/kg Felis catus 80.0 %
Compound was tested for neuronal inhibition of postganglionic cardio accelerator nerve stimulation in anaesthetized cat at 2 Hz frequency at 3 mg/kg Felis catus 23.0 %
Inhibitory activity against Dopamine receptor D2 in calf corpus striatum using [3H]spiperone as radioligand None 48.0 nM
Dopamine receptor binding affinity by displacing the radioligand [3H]-dopamine from dopamine receptor. Bos taurus 18.0 nM
Dopamine receptor binding affinity by displacing the radioligand [3H]spiroperidol from dopamine receptor. Bos taurus 145.0 nM
In vitro inhibitory activity against dopamine receptor from calf caudate using [3H]dopamine as radioligand None 18.0 nM
In vitro inhibitory activity against dopamine receptor from calf caudate using [3H]spiperone as radioligand None 145.0 nM
Dopaminergic activity assessed in vitro for displacement of [3H]apomorphine from specific binding sites on rat striatal membranes None 3.1 nM
In vitro affinity for dopamine receptor by displacement of [3H]- apomorphine in rat striatal membranes Rattus norvegicus 3.1 nM
Affinity towards Dopamine receptor D2 None 50.0 nM
Binding affinity towards Dopamine receptor D2 by displacement of [3H]U-86170. Homo sapiens 4.0 nM
Inhibitory activity against Dopamine receptor D2 in rat corpus striatum using [3H]Apomorphine as radioligand None 1.6 nM
In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes. None 4.0 nM
In vitro affinity at mutant D2 receptor (S194A) in C6 (glioma) cell membranes. None 45.0 nM
In vitro affinity at mutant D2 receptor (S197A) in C6 (glioma) cell membranes. None 40.0 nM
In vitro affinity at wild type Dopamine receptor D2 on C6 (glioma) cell membranes. None 30.0 nM
Compound was tested for antagonistic activity against D2 receptor from rat striatum, used [3H]raclopride as radioligand None 1.0 nM
Binding affinity towards Dopamine receptor D3 by displacement of [3H](+)-7-OH-DPAT. Homo sapiens 4.0 nM
Evaluated for the prolactin inhibition at the dose 50 ug/kg administered intraperitoneally Rattus norvegicus 95.0 %
Evaluated for the prolactin inhibition at the dose 50 ug/kg administered intraperitoneally (treatment) Rattus norvegicus 1.6 ng ml-1
Inhibition of serum prolactin concentration in rats when 5 mg/Kg was administered intraperitoneally Rattus norvegicus 88.0 %
In vitro inhibitory activity against serotonin receptor from rat frontal cortex using [3H]spiperone as radioligand Rattus norvegicus 140.0 nM
In vitro inhibitory activity against serotonin receptor from whole rat brain using [3H]5-HT as radioligand Rattus norvegicus 385.0 nM
Inhibition of [3H]apomorphine binding to dopamine receptor of rat corpus striatum None 1.6 nM
Inhibition of [3H]dopamine binding to dopamine receptor of rat corpus striatum None 4.1 nM
Inhibition of [3H]spiperone binding to dopamine receptor of rat corpus striatum None 48.0 nM
Inhibition constant against [3H]-spiperone binding to human Dopamine receptor D3 expressed in CHO cells Homo sapiens 0.8511 nM
Inhibition of human ERG Homo sapiens 120.23 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 15.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1A radioligand binding (ligand: [3H] 8-OH-DPAT) None 8.468 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 87.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT1B radioligand binding (ligand: [125I] Cyanopindolol) Rattus norvegicus 40.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 14.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 3.904 nM
DRUGMATRIX: Alpha-1A adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 781.0 nM
DRUGMATRIX: Alpha-1D adrenergic receptor radioligand binding (ligand: prazosin) None 744.0 nM
DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 264.0 nM DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) None 99.0 nM
DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 64.0 nM DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscine) None 29.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 205.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 76.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 49.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 379.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: [3H] Mesulergine) None 199.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 39.0 nM DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 18.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 913.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 887.0 nM
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 200.0 nM
DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 679.0 nM DRUGMATRIX: Dopamine D1 radioligand binding (ligand: [3H] SCH-23390) None 339.0 nM
DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 111.0 nM DRUGMATRIX: Dopamine D2L radioligand binding (ligand: [3H] Spiperone) None 37.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 5.393 nM DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 1.832 nM
Agonist activity at Rattus norvegicus (rat) dopamine D2/D3 receptor transfected in african green monkey COS7 cells assessed as inhibition of forskolin-stimulated adenylyl cyclase activity after 10 min Rattus norvegicus 4.31 nM
Agonist activity at Rattus norvegicus (rat) dopamine D2 receptor transfected in african green monkey COS7 cells assessed as inhibition of forskolin-stimulated adenylyl cyclase activity after 10 min Rattus norvegicus 7.86 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) wild type dopamine D3 receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 5.12 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D3 trunk/D3 tail receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 2.41 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D3 trunk/D2 tail receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 5.85 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D2 trunk/D3 tail receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 5.59 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) wild type dopamine D2 receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 32.0 nM
Displacement of [3H]nemonapride from Rattus norvegicus (rat) chimeric dopamine D2 trunk/D2 tail receptor transfected in african green monkey COS7 cells after 1 hr by beta scintillation counting Rattus norvegicus 27.5 nM
Displacement of [125]iodosulpride from human recombinant dopamine D2L receptor expressed in CHO cells after 30 mins Homo sapiens 26.0 nM Displacement of [125]iodosulpride from human recombinant dopamine D2L receptor expressed in CHO cells after 30 mins Homo sapiens 25.7 nM
Agonist activity at dopamine D2 receptor short isoform (unknown origin) expressed in mouse NIH/3T3 cells by R-SAT assay Homo sapiens 0.3548 nM
Agonist activity at 5HT2A receptor (unknown origin) expressed in mouse NIH/3T3 cells by R-SAT assay Homo sapiens 8.913 nM
Agonist activity at 5HT2C receptor VGV isoform (unknown origin) expressed in mouse NIH/3T3 cells by R-SAT assay Homo sapiens 218.78 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 17.72 %
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 0.27 % 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 0.27 %

Cross References

Resources Reference
ChEBI 63617
ChEMBL CHEMBL531
DrugBank DB01186
DrugCentral 2105
FDA SRS 24MJ822NZ9
Human Metabolome Database HMDB0015317
Guide to Pharmacology 48
KEGG C07425
PharmGKB PA450873
PubChem 47811
SureChEMBL SCHEMBL26921
ZINC ZINC000003786466