HISTAMINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII 820484N8I3
EPA CompTox DTXSID4023125

Structure

InChI Key NTYJJOPFIAHURM-UHFFFAOYSA-N
Smiles NCCc1c[nH]cn1
InChI
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)

Physicochemical Descriptors

Property Name Value
Molecular Formula C5H9N3
Molecular Weight 111.15
AlogP -0.09
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 54.7
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 8.0
Assay Description Organism Bioactivity Reference
Compound was evaluated for mepyramine antagonism effects in guinea pig aorta (relaxation) at a mepyramine concentration of 100 nM Cavia porcellus 10.0 nM
Compound was evaluated for mepyramine antagonism effects in guinea pig ileum (contraction) at a mepyramine concentration of 100 nM Cavia porcellus 0.7762 nM
In vitro H1 agonistic activity by taking guinea pig ileum contraction Cavia porcellus 140.0 nM
In vitro chronotropic effect of histamine at 5 ug/mL in guinea pig atrium Cavia porcellus 980.0 nM
In vitro contractile response of histamine at 0.5 ug/mL in guinea pig ileum Cavia porcellus 240.0 nM
Full pA2 value of compound at 0.3-100 nM concentration of mepyramine in guinea pig ileum Cavia porcellus 0.8511 nM
Effective concentration for agonism activity in Endothelium-Denuded guinea pig aortic segment Cavia porcellus 316.23 nM
Effective concentration for agonism activity in guinea pig ileal whole segment Cavia porcellus 199.53 nM
Binding affinity towards histamine H3 receptor using [3H](R)-alpha-methylhistamine as radioligand in guinea pig cortical homogenates Cavia porcellus 0.1445 nM
Binding affinity towards histamine H3 receptor using [3H](R)-alpha-methylhistamine as radioligand in guinea pig ileum LMMP homogenates Cavia porcellus 10.47 nM
Inhibition of human Histamine H3 receptor using [3H]N-alpha-methyl histamine Homo sapiens 77.0 nM
Inhibition of the forskolin-stimulated cAMP production in SK-N-MC cells expressing human Histamine H3 receptor None 4.074 nM
Inhibitory activity determined by the inhibition of cAMP- stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H3 receptor None 9.772 nM
Histamine H3 receptor competition binding using [3H]Na-methylhistamine None 33.88 nM
Inhibitory activity measured by [3H]- N alpha- methyl-histamine binding to membranes of SK-N-MC cells expressing the human Histamine H3 receptor None 9.333 nM
Compound was evaluated for mepyramine antagonism effects in guinea pig aorta (contraction) at a mepyramine concentration of 100 nM Cavia porcellus 1.0 nM
Contractile effects antagonized by mepyramine (0.3-100 nM) against Histamine H1 receptor in guinea pig ileum Cavia porcellus 0.8511 nM
Compound was tested for the contractile effects antagonized by mepyramine (1-1000 nM) against Histamine H1 receptor of guinea pig aorta. Cavia porcellus 0.7762 nM
Relative potency against Histamine H1 receptor in endothelium-Denuded rings of guinea pig Aorta Cavia porcellus 1.0 nM
Effective concentration against histamine H1 receptor in endothelium-Denuded rings of guinea pig Aorta Cavia porcellus 162.18 nM
Effective concentration against histamine H1 receptor in guinea pig ileum Cavia porcellus 199.53 nM
Inhibition of human Histamine H1 receptor using [3H]pyrilamine Homo sapiens 13.0 nM
Inhibitory activity against human Histamine H1 receptor None 158.49 nM
Relative potency against Histamine H1 receptor in rat aorta None 10.0 nM
Inhibition of human Histamine H2 receptor using [3H]tiotidine Homo sapiens 463.0 nM
In vitro binding affinity was measured against Histamine H3 receptor on rat cerebral cortex. None 6.31 nM
Inhibition of human Histamine H4 receptor Homo sapiens 75.0 nM
Inhibition of the forskolin-stimulated cAMP production in SK-N-MC cells expressing human Histamine H4 receptor None 20.89 nM
Inhibitory activity determined by the inhibition of cAMP- stimulated beta-galactosidase transcription in SK-N-MC cells expressing the human Histamine H4 receptor None 54.95 nM
Inhibition of [3H]-histamine binding to membranes of SK-N-MC cells expressing the human Histamine H4 receptor Homo sapiens 14.45 nM
Compound was evaluated for mepyramine antagonism effects in guinea pig ileum (contraction) at a mepyramine concentration of 100 nM Cavia porcellus 0.8511 nM
In vitro H3 agonistic activity against K+ induced histamine in slices of rat brain cortex. Rattus norvegicus 62.0 nM
Binding affinity towards human histamine H4 receptor was determined by [3H]Na-methylhistamine binding to SK-N-MC cell membranes Homo sapiens 7.943 nM
Agonist activity at histamine H1 receptor in guinea pig ileum Cavia porcellus 199.53 nM
Agonist activity at human H1 receptor expressed in 293-EBNA cells by luciferase reporter gene assay Homo sapiens 45.0 nM
Agonist activity at human H2 receptor expressed in 293-EBNA cells by luciferase reporter gene assay Homo sapiens 650.0 nM
Agonist activity at human H3 receptor expressed in 293-EBNA cells by luciferase reporter gene assay Homo sapiens 88.0 nM
Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK293T cells Homo sapiens 12.02 nM
Activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay Homo sapiens 190.0 nM
Activity at human recombinant histamine H3 receptor expressed in Sf9 cells coexpressing Galphai, G-beta-1-gamma-2 and RGS4 by steady-state GTPase activity assay Homo sapiens 25.1 nM
Activity at human recombinant histamine H4 receptor-RGS4 fusion protein expressed in Sf9 cells coexpressing Galphai2 and G-beta-1-gamma-2 by steady-state GTPase activity assay Homo sapiens 11.6 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 4.1 %
Displacement of [3H]histamine from human histamine H4 receptor expressed in SK-NM-C cells Homo sapiens 13.4 nM
Agonist activity at human H1 receptor expressed in insect Sf9 cells co-expressing RGS4 assessed as gamma[32P]GTP binding by liquid scintillation counting Homo sapiens 190.55 nM
Agonist activity at human H3 receptor expressed in insect Sf9 cells co-expressing Gialpha2, Gbeta1gamma2 and RGS4 assessed as gamma[32P]GTP binding by liquid scintillation counting Homo sapiens 25.12 nM
Agonist activity at human H4 receptor expressed in insect Sf9 cells co-expressing RGS19 fusion protein and Gialpha2, Gbeta1gamma2 assessed as gamma[32P]GTP binding by liquid scintillation counting Homo sapiens 12.02 nM
Displacement of 3-([1,1,1-3H]methyl)-2-(4-{[3-(1-pyrrolidinyl)propyl]oxy}phenyl)-4(3H)-quinazolinone from mouse histamine H3 receptor expressed in HEK293 cells Mus musculus 68.0 nM
Agonist activity at human histamine H4 receptor expressed in Sf9 cells co-expressing Galphai2 and Gbeta1gamma2 assessed as stimulation of [35S]GTPgammaS binding Homo sapiens 13.8 nM
Agonist activity at human histamine H4 receptor expressed in Sf9 cells co-expressing Galphai2 and Gbeta1gamma2 assessed as stimulation of GTPase by [gamma-32P]GTP spontaneous degradation assay Homo sapiens 11.75 nM
Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK293T cells Homo sapiens 12.02 nM
Agonist activity at human histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase assay Homo sapiens 190.55 nM
Agonist activity at human histamine H3 receptor expressed in Sf9 cells coexpressing Gialpha-2-Gbeta-1-gamma-2 and RGS4 proteins protein by steady-state GTPase assay Homo sapiens 25.12 nM
Agonist activity at human histamine H4 receptor expressed in Sf9 cells coexpressing RGS19 protein by steady-state GTPase assay Homo sapiens 12.02 nM
Activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay Homo sapiens 190.55 nM
Activity at human recombinant histamine H3 receptor expressed in Sf9 cells coexpressing Galphai, Gbeta1gamma2 and RGS4 by steady-state GTPase activity assay Homo sapiens 12.88 nM
Activity at human recombinant GAIP-fused histamine H4 receptor expressed in Sf9 cells coexpressing Galphai, Gbeta1gamma2 by steady-state GTPase activity assay Homo sapiens 9.12 nM
Displacement of [3H[N-alpha-methylhistamine form human recombinant histamine H3 receptor expressed in CHO cells after 1 hr by liquid scintillation counting Homo sapiens 5.2 nM
Agonist activity at human recombinant histamine H3 receptor expressed in CHO cells assessed as [35S]GTPgammaS binding after 1 hr by liquid scintillation counting Homo sapiens 640.0 nM
Displacement of [3H]histamine from human recombinant histamine H4 receptor Homo sapiens 60.0 nM
Agonist activity at rat histamine H4 receptor by luciferase reporter gene assay Rattus norvegicus 158.49 nM
Binding affinity to dog histamine H4 receptor expressed in COS7 cells by radioligand displacement assay Canis lupus familiaris 63.1 nM
Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 by steady-state GTPase activity assay Homo sapiens 199.53 nM
Displacement of [3H]-histamine from human histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 Homo sapiens 7.943 nM
Agonist activity at human recombinant histamine H4 receptor expressed in Sf9 cells coexpressing RGS19, Galphai2, Gbeta1gamma2 by steady-state GTPase activity assay Homo sapiens 12.59 nM
Displacement of [3H]Nalpha-methylhistamine from human histamine H3 receptor expressed in human SK-N-MC cells Homo sapiens 10.0 nM
Agonist activity at human histamine H3 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay Homo sapiens 5.012 nM
Agonist activity at human histamine H4 receptor expressed in human SK-N-MC cells by CRE-beta galactosidase reporter gene assay Homo sapiens 19.95 nM
Binding affinity to human recombinant histamine H4 receptor expressed in human SK-N-MC cells by radioligand displacement assay Homo sapiens 12.59 nM
Agonist activity at human recombinant histamine H4 receptor expressed in human SK-N-MC cells co-expressing SRE-Luc by luciferase reporter gene assay Homo sapiens 79.43 nM
Binding affinity to mouse histamine H4 receptor expressed in human SK-N-MC cells by radioligand displacement assay Mus musculus 79.43 nM
Binding affinity to rat histamine H4 receptor expressed in human SK-N-MC cells by radioligand displacement assay Rattus norvegicus 63.1 nM
Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by firefly luciferase reporter gene assay Plasmodium falciparum 660.0 nM
Displacement of [3H]N-alpha-methylhistamine from human histamine H3 receptor expressed in HEK293 cells after 60 mins by liquid scintillation counting Homo sapiens 11.75 nM
Displacement of [3H]histamine from human histamine H4 receptor expressed in HEK293 cells after 60 mins by liquid scintillation counting Homo sapiens 12.02 nM
Agonist activity at human histamine H4 receptor expressed in HEK293 cells assessed by forskolin induced cAMP response element activation by luciferase reporter gene assay Homo sapiens 25.12 nM
Agonist activity at human histamine H3 receptor expressed in HEK293 cells assessed by forskolin induced cAMP response element activation by luciferase reporter gene assay Homo sapiens 15.85 nM
Displacement of [3H]histamine from human H3 receptor expressed in HEK293 cells after 1 to 1.5 hrs by scintillation counting Homo sapiens 6.31 nM
Displacement of [3H]histamine from human H4 receptor expressed in HEK293 cells after 1 to 1.5 hrs by scintillation counting Homo sapiens 15.85 nM
Displacement of [3H]histamine from human H4 receptor expressed in HEK cell membranes Homo sapiens 9.0 nM
Displacement of [3H]histamine from wild type human histamine H4 receptor transfected in HEK293T cells after 1 hr by liquid scintillation counting analysis Homo sapiens 19.95 nM
Agonist activity at human recombinant histamine H4 receptor-RGS19 fusion protein expressed in Sf9 cells coexpressing Galphai2,Gbeta1gamma2 assessed as [35S]GTPgammaS binding after 90 mins by liquid scintillation counting Homo sapiens 20.42 nM
Agonist activity at human recombinant histamine H3 receptor expressed in Sf9 cells coexpressing Galphai2,Gbeta1gamma2 and RGS4 assessed as [35S]GTPgammaS binding after 90 mins by liquid scintillation counting Homo sapiens 12.88 nM
Agonist activity at human recombinant histamine H4 receptor-RGS19 fusion protein expressed in Sf9 cells coexpressing Galphai2,Gbeta1gamma2 preincubated for 2 mins before [gamma32P]GTP addition measured after 20 mins by steady-state GTPase activity assay Homo sapiens 12.02 nM
Agonist activity at human recombinant histamine H3 receptor expressed in Sf9 cells coexpressing Galphai2,Gbeta1gamma2 and RGS4 preincubated for 2 mins before [gamma32P]GTP addition measured after 20 mins by steady-state GTPase activity assay Homo sapiens 25.12 nM
Agonist activity at human recombinant histamine H1 receptor expressed in Sf9 cells coexpressing RGS4 preincubated for 2 mins before [gamma32P]GTP addition measured after 20 mins by steady-state GTPase activity assay Homo sapiens 190.55 nM
Binding affinity to histamine H4 receptor (unknown origin) Homo sapiens 8.0 nM
Binding affinity to histamine H3 receptor (unknown origin) Homo sapiens 16.0 nM
Binding affinity to human histamine H4 receptor Homo sapiens 4.8 nM
Binding affinity to guinea pig histamine H4 receptor Cavia porcellus 6.0 nM
Binding affinity to mouse histamine H4 receptor Mus musculus 42.0 nM
Binding affinity to rat histamine H4 receptor Rattus norvegicus 136.0 nM
Displacement of [3H]-histamine from human histamine H4 receptor expressed in human SK-N-MC cells after 1 hr Homo sapiens 15.85 nM
Antagonist activity at human histamine 4 receptor expressed in Sf9 cell membranes co-expressing Galphai2 and Gbeta1gamma2 assessed as [35S]GTPgammaS binding by scintillation counting Homo sapiens 7.943 nM
Agonist activity at human histamine H3 receptor expressed in sf9 cell membrane co-expressing mammalian Galphai2 and Gbeta1gamma2 incubated for 90 mins by [35S]GTPgammaS binding assay Homo sapiens 13.0 nM
Agonist activity at human histamine H4 receptor expressed in sf9 cell membrane co-expressing mammalian Galphai2 and Gbeta1gamma2 incubated for 90 mins by [35S]GTPgammaS binding assay Homo sapiens 11.0 nM
Agonist activity at human histamine H1 receptor expressed in sf9 cell membrane co-expressing RGS4 or RGS9 assessed as increase in 32Pi level incubated for 20 mins by liquid scintillation counting in presence of [gamma32P]GTP Homo sapiens 190.0 nM
Agonist activity at human SF-His6-tagged histamine H4 receptor expressed in HEK293 cells assessed as inhibition of forskolin-stimulated response incubated for 5 hrs by luciferase reporter gene assay Homo sapiens 13.0 nM
Agonist activity at mouse SF-His6-tagged histamine H4 receptor expressed in HEK293 cells assessed as inhibition of forskolin-stimulated response incubated for 5 hrs by luciferase reporter gene assay Mus musculus 94.0 nM
Binding affinity to histamine H4 receptor (unknown origin) Homo sapiens 1.6 nM
Binding affinity to histamine H3 receptor (unknown origin) Homo sapiens 12.8 nM
Binding affinity to human H4R Homo sapiens 5.0 nM
Binding affinity to mouse H4R Mus musculus 42.0 nM
Binding affinity to rat H4R Rattus norvegicus 134.0 nM
Agonist activity at human H4R by [35S]-GTPgammaS-binding assay Homo sapiens 7.413 nM
Agonist activity at human H4R expressed in HEK293-SF-hH4R-His6-CRE-Luc cells incubated for 5 hrs by luciferase reporter gene assay Homo sapiens 16.98 nM
Agonist activity at human H4R expressed in HEK293T-beta-arr2-hH4R cells by beta-arrestin2 recruitment assay Homo sapiens 33.88 nM
Agonist activity at mouse H4R expressed in HEK293-SF-mH4R-His6-CRE-Luc cells incubated for 5 hrs by luciferase reporter gene assay Mus musculus 87.1 nM
Agonist activity at rat H4R expressed in HEK293-SF-rH4R-His6-CRE-Luc cells incubated for 5 hrs by luciferase reporter gene assay Rattus norvegicus 295.12 nM
Displacement of [3H]NAMH from human H3R expressed in HEK293T cells incubated for 2 hrs by microbeta scintillation counting analysis Homo sapiens 12.59 nM
Agonist activity at human H3R expressed on HEK293T cells assessed as inhibition of forskolin-induced CRE-driven luciferase activity co-incubated with forskolin for 6 hrs and measured after 30 mins by CRE-luciferase reporter gene assay Homo sapiens 2.512 nM
Agonist activity at human H3R expressed on HEK293T cells by [35S]GTPgammaS binding assay Homo sapiens 63.1 nM
Displacement of [3H]-N-alpha-methylhistamine from human histamine H3 receptor expressed in SK-N-MC cells incubated for 40 min by liquid scintillation counting analysis Homo sapiens 10.0 nM
Agonist activity at human H3R expressed on SK-N-MC cells assessed as inhibition of forskolin-induced beta galactosidase activity preincubated with forskolin for 6 hrs followed compound addition by CRE-luciferase reporter gene assay Homo sapiens 5.012 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 19.79 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.67 %
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 0.03 % 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 0.3 % 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 0.03 % 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 0.3 %
Displacement of [3H]UR-DE257 from Gsalphas-coupled human H2R expressed in baculovirus infected Sf9 cells incubated for 60 mins by scintillation counting method Homo sapiens 295.12 nM
Agonist activity at human H3 receptor stably transfected in CHO-DUKX cells assessed as increase in cAMP accumulation by measuring reduction in forskolin level by HitHunter-cAMP assay Homo sapiens 30.0 nM
Agonist activity at human H3 receptor expressed in CHO cells assessed as increase in cAMP accumulation by measuring reduction in forskolin level incubated for 4 hrs by CRE/MRE-luciferase reporter gene assay Homo sapiens 4.0 nM
Displacement of [3H]-Histamine from human histamine 4 receptor transfected in HEK293T cells incubated for 16 hrs by liquid scintillation counter analysis Homo sapiens 1.0 nM
Displacement of [3H]-Histamine from human histamine 3 receptor transfected in HEK293T cells incubated for 16 hrs by liquid scintillation counter analysis Homo sapiens 2.512 nM
Displacement of [3H]UR-DE257 from human histamine H2 receptor expressed in sf9 insect cell membranes co-expressing GSalphaS incubated for 60 mins by microbeta scintillation counting method Homo sapiens 263.03 nM
Displacement of [3H]UR-P129 from human histamine H3 receptor expressed in sf9 insect cell membranes co-expressing Galphai2/Gbeta1gamma2 incubated for 60 mins by microbeta scintillation counting method Homo sapiens 25.7 nM
Displacement of [3H]histamine from human histamine H4 receptor expressed in sf9 insect cell membranes co-expressing Galphai2/Gbeta1gamma2 incubated for 60 mins by microbeta scintillation counting method Homo sapiens 25.12 nM
Agonist activity at guinea pig right atrium histamine H2 receptor assessed as increase in heart rate incubated for 30 mins in presence of cimetidine Cavia porcellus 691.83 nM
Agonist activity at human histamine receptor expressed in sf9 insect cell membranes co-exprssing GsalphaS incubated for 90 mins [35S]GTPgammaS binding based microbeta scintillation counting analysis Homo sapiens 977.24 nM
Binding affinity in Nluc-hH3R assessed in HEK293 cells by NanoBRET binding assay Homo sapiens 588.84 nM
Binding affinity in Nluc-hH3R assessed in HEK293T cells by NanoBRET binding assay Homo sapiens 501.19 nM
Agonist activity at human H2 receptor expressed in HEK293T-ARRB2 cells assessed as stimulation of beta-arrestin 2 recruitment Homo sapiens 114.82 nM
Displacement of [3H]UR-DE257 from Gsalphas-coupled human H2R expressed in Sf9 cell membranes by competitive binding assay Homo sapiens 263.03 nM

Cross References

Resources Reference
ChEBI 18295
ChEMBL CHEMBL90
DrugBank DB05381
DrugCentral 1375
FDA SRS 820484N8I3
Human Metabolome Database HMDB0000870
Guide to Pharmacology 1247
KEGG C00388
PDB HSM
PubChem 774
SureChEMBL SCHEMBL2279
ZINC ZINC000000388081
CONTENTS