Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H9N3.ClH |
| Molecular Weight | 147.606 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCCC1=CNC=N1
InChI
InChIKey=IVCJGQQPPHYHBS-UHFFFAOYSA-N
InChI=1S/C5H9N3.ClH/c6-2-1-5-3-7-4-8-5;/h3-4H,1-2,6H2,(H,7,8);1H
| Molecular Formula | C5H9N3 |
| Molecular Weight | 111.1451 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Histamine is a depressor amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and a centrally acting neurotransmitter. Phosphate salt of jistamine was used as a diagnostic aid for evaluation of gastric acid secretory function. In addition, this compound is used as a positive control in evaluation of allergenic (immediate hypersensitivity or "Type I") skin testing. In addition, histamine is being studied for treatment of multiple sclerosis. It was approved, that histamine physiological functions are mediated by four 7-transmembrane G protein-coupled receptors (H1R, H2R, H3R, H4R) that are all targets of pharmacological intervention. The receptors display molecular heterogeneity and constitutive activity. H1R antagonists are long known antiallergic and sedating drugs, whereas the H2R led to the development of H2R-antagonists that revolutionized stomach ulcer treatment. The H3R is an auto receptor and heteroreceptor providing negative feedback on histaminergic and inhibition on other neurons. The H4R occurs on immuncompetent cells and the development of anti-inflammatory drugs is anticipated.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
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Target ID: CHEMBL1941 |
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Target ID: CHEMBL264 |
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Target ID: CHEMBL3759 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | HISTAMINE PHOSPHATE Approved UseIndications and Usage Uses temporarily relieves symptoms due to sinus discomforts associated with inflamed sinuses, hay fever or upper respiratory allergies: sinus pain and pressure runny nose sinus headaches sore throat nasal congestion dry mucus membranes sneezing itchy, burning eyes Reference image sinus.jpg Launch Date1939 |
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| Primary | Unknown Approved UseUnknown |
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| Diagnostic | HISTAMINE PHOSPHATE Approved UseHistamine phosphate is indicated as a diagnostic aid for evaluation of gastric acid secretory function. Anacidity (achlorhydria) in response to histamine may indicate pernicious anemia, atrophic gastritis, adenomatous polyps of stomach, or gastric carcinoma. Gastric hypersecretion in response to histamine may indicate duodenal ulcer or the Zollinger-Ellison syndrome. Launch Date1939 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1877 nM × min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12092744 |
1 mg single, subcutaneous dose: 1 mg route of administration: Subcutaneous experiment type: SINGLE co-administered: |
HISTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.03 mg single, intravenous Highest studied dose Dose: 0.03 mg Route: intravenous Route: single Dose: 0.03 mg Sources: |
unhealthy n = 4 Health Status: unhealthy Condition: asthma Sex: M Population Size: 4 Sources: |
|
0.2 mg single, intramuscular Highest studied dose Dose: 0.2 mg Route: intramuscular Route: single Dose: 0.2 mg Sources: |
unhealthy n = 1 Health Status: unhealthy Condition: asthma Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Pharmacological studies of antipsychotic drug, penfluridol. 2. General pharmacological properties]. | 1976 Jul |
|
| Diesel exhaust particulates upregulate histamine receptor mRNA and increase histamine-induced IL-8 and GM-CSF production in nasal epithelial cells and endothelial cells. | 1999 Jan |
|
| Selective substrates for non-neuronal monoamine transporters. | 1999 Jul |
|
| Histamine and histamine-receptor antagonists modify gene expression and biosynthesis of interferon gamma in peripheral human blood mononuclear cells and in CD19-depleted cell subsets. | 1999 Nov 1 |
|
| H2 histamine receptor-mediated increase in intracellular Ca2+ in cultured human keratinocytes. | 1999 Sep |
|
| Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets. | 2000 Apr 12 |
|
| Identification of a histamine H(3)-like receptor in the zebrafish (Danio rerio) brain. | 2000 Aug |
|
| Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain. | 2000 Dec |
|
| Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles. | 2000 Jun |
|
| Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells. | 2000 Jun |
|
| Histamine up-regulates phosphodiesterase 4 activity and reduces prostaglandin E2-inhibitory effects in human neutrophils. | 2000 Nov |
|
| Predictive markers of asthma exacerbation during stepwise dose reduction of inhaled corticosteroids. | 2001 Feb |
|
| Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial. | 2001 Feb |
|
| Acquisition and alteration of adhesion molecules during cultured human mast cell differentiation. | 2001 Feb |
|
| Histamine prevents polyamine accumulation in mouse C57.1 mast cell cultures. | 2001 Feb |
|
| Double-blind, placebo-controlled food challenge with apple. | 2001 Feb |
|
| Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells. | 2001 Feb |
|
| Nedocromil sodium inhibits histamine-induced itch and flare in human skin. | 2001 Feb |
|
| Ontogeny of modulatory inputs to motor networks: early established projection and progressive neurotransmitter acquisition. | 2001 Feb 15 |
|
| IL-13 overexpression predisposes to anaphylaxis following antigen sensitization. | 2001 Feb 15 |
|
| Involvement of central histaminergic neurons in polypnea induced by hyperthermia in rabbits. | 2001 Feb 2 |
|
| Comparison of montelukast and fexofenadine for chronic idiopathic urticaria. | 2001 Jan |
|
| Preclinical profile of the monodisperse iodinated macromolecular blood pool agent P743. | 2001 Jan |
|
| Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis. | 2001 Jan |
|
| Combination therapy with anti-mediator drugs in allergic disease. | 2001 Jan |
|
| Urticaria induced by cetirizine. | 2001 Jan |
|
| Interleukin-4-positive mast cells are highly associated with the extent of immediate allergic wheal reaction in the skin. | 2001 Jan |
|
| Effects of BP 2-94, a selective H(3)-receptor agonist, on blood flow and vascular permeability of the rat mandibular incisor pulp. | 2001 Jan |
|
| Effect of the long-acting tachykinin NK(1) receptor antagonist MEN 11467 on tracheal mucus secretion in allergic ferrets. | 2001 Jan |
|
| Antihistamines. | 2001 Jan |
|
| Dysregulation of the IgE/Fc epsilon RI network in HIV-1 infection. | 2001 Jan |
|
| Potentiation by histamine of synaptically mediated excitotoxicity in cultured hippocampal neurones: a possible role for mast cells. | 2001 Jan |
|
| Spinothalamic lamina I neurons selectively sensitive to histamine: a central neural pathway for itch. | 2001 Jan |
|
| A neural pathway for itch. | 2001 Jan |
|
| Expression of humanized Fab fragments that recognize the IgE-binding domain of human Fc(epsilon)RIalpha in COS and CHO cells. | 2001 Jan |
|
| Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores. | 2001 Jan |
|
| In vitro catabolism of histidine by mixed rumen bacteria and protozoa. | 2001 Jan |
|
| Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. | 2001 Jan 1 |
|
| delta-opioid receptors inhibit neurogenic intestinal secretion evoked by mast cell degranulation and type I hypersensitivity. | 2001 Jan 1 |
|
| The rat H3 receptor: gene organization and multiple isoforms. | 2001 Jan 12 |
|
| Nitric oxide synthase inhibitors have opposite effects on acute inflammation depending on their route of administration. | 2001 Jan 15 |
|
| Luminal Nalpha-methyl histamine stimulates gastric acid secretion in duodenal ulcer patients via releasing gastrin. | 2001 Jan 26 |
|
| Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
|
| Pharmacological characterization of the rat paw edema induced by Bothrops lanceolatus (Fer de lance) venom. | 2001 Jun |
|
| Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport. | 2001 Mar |
|
| Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin. | 2001 Mar |
|
| Complement-dependent immune complex-induced bronchial inflammation and hyperreactivity. | 2001 Mar |
|
| Decreased brain histamine-releasing factor protein in patients with Down syndrome and Alzheimer's disease. | 2001 Mar 2 |
|
| Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens. | 2001 Mar 30 |
|
| Transcriptional activation of the rat vesicular monoamine transporter 2 promoter in gastric epithelial cells: regulation by gastrin. | 2001 Mar 9 |
Sample Use Guides
The skin in the test area should be cleansed with alcohol and air dried.
The histamine control skin test solution should be placed at the same site with the other skin test antigens, either on the patient's back or on the volar surface of the forearm. The patient should be placed in a comfortable position before the testing is begun.
For the prick test, a sharp needle is used to puncture the skin, but not to draw blood. If the scratch test is used, carefully break or scratch the skin with a sterile scarifier. Do not draw blood. Each scratch should be about 2 mm - 4 mm in length.
A small drop of the histamine base 1 mg/mL (Histamine Phosphate 2.75 mg/mL) is placed on the abraded skin site no closer than 4 or 5 cm from an adjacent test site. Some physicians prefer to place the solution on the test area and then prick through the drop with a sharp needle.
Route of Administration:
Parenteral
Histamine prevented monocytic apoptosis induced by serum deprivation, CD95/Fas ligation, or dexamethasone in a dose- and time-dependent fashion. The inhibitory effects of histamine on monocytic apoptosis were blocked by an H2R antagonist, and mimicked by an H2R agonist. Histamine also up-regulated the expression of Bcl-2 and Mcl-1, and inhibited the activation of caspase-3. The culture supernatants from histamine-treated monocytes inhibited monocytic apoptosis, which was partly reversed by the removal of IL-10. Monocytes cultured with anti-IL-10 mAb and histamine did not exhibit an inhibitory effect on apoptosis. The histamine-induced anti-apoptotic effect was attenuated when monocytes were cultured in the presence of a cAMP inhibitor.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:12:43 GMT 2023
by
admin
on
Fri Dec 15 19:12:43 GMT 2023
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| Record UNII |
F9I23AC4PQ
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| Record Status |
Validated (UNII)
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| Record Version |
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55-36-7
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SUB25473
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F9I23AC4PQ
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100000089482
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120160
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
