Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H9N3 |
Molecular Weight | 111.1451 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC1=CNC=N1
InChI
InChIKey=NTYJJOPFIAHURM-UHFFFAOYSA-N
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
Molecular Formula | C5H9N3 |
Molecular Weight | 111.1451 |
Charge | 0 |
Count |
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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 |
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Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16648669 |
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Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084539 |
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Target ID: CHEMBL264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17652997 |
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Target ID: CHEMBL3759 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084539 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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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 |
PubMed
Title | Date | PubMed |
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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 |
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Selective substrates for non-neuronal monoamine transporters. | 1999 Jul |
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Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets. | 2000 Apr 12 |
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Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles. | 2000 Jun |
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Assessment and treatment of laboratory animal allergy. | 2001 |
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Predictive markers of asthma exacerbation during stepwise dose reduction of inhaled corticosteroids. | 2001 Feb |
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Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial. | 2001 Feb |
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IL-18 might reflect disease activity in mild and moderate asthma exacerbation. | 2001 Feb |
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Histamine prevents polyamine accumulation in mouse C57.1 mast cell cultures. | 2001 Feb |
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Inhibitory action of water soluble fraction of Terminalia chebula on systemic and local anaphylaxis. | 2001 Feb |
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Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells. | 2001 Feb |
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A human tissue-engineered vascular media: a new model for pharmacological studies of contractile responses. | 2001 Feb |
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IL-13 overexpression predisposes to anaphylaxis following antigen sensitization. | 2001 Feb 15 |
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Selective down-regulation of high-affinity IgE receptor (FcepsilonRI) alpha-chain messenger RNA among transcriptome in cord blood-derived versus adult peripheral blood-derived cultured human mast cells. | 2001 Feb 15 |
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Involvement of central histaminergic neurons in polypnea induced by hyperthermia in rabbits. | 2001 Feb 2 |
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Food-deprived activity stress decreased the activity of the histaminergic neuron system in rats. | 2001 Feb 9 |
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Comparison of montelukast and fexofenadine for chronic idiopathic urticaria. | 2001 Jan |
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Preclinical profile of the monodisperse iodinated macromolecular blood pool agent P743. | 2001 Jan |
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The dyspepsia alphabet: DU, GU, GERD, NERD, NUD/FD and UD. | 2001 Jan |
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Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis. | 2001 Jan |
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Combination therapy with anti-mediator drugs in allergic disease. | 2001 Jan |
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Urticaria induced by cetirizine. | 2001 Jan |
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The treatment of rhinovirus infections: progress and potential. | 2001 Jan |
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Effect of acute metabolic acid/base shifts on the human airway calibre. | 2001 Jan |
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Antihistamines. | 2001 Jan |
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Effects of cetirizine and epinastine on the skin response to histamine iontophoresis. | 2001 Jan |
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Management of severe gastroesophageal reflux disease. | 2001 Jan |
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Acidification of formula reduces bacterial translocation and gut colonization in a neonatal rabbit model. | 2001 Jan |
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Cortical acetylcholine release elicited by stimulation of histamine H1 receptors in the nucleus basalis magnocellularis: a dual-probe microdialysis study in the freely moving rat. | 2001 Jan |
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Expression of humanized Fab fragments that recognize the IgE-binding domain of human Fc(epsilon)RIalpha in COS and CHO cells. | 2001 Jan |
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Identification of rat H3 receptor isoforms with different brain expression and signaling properties. | 2001 Jan |
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Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. | 2001 Jan 1 |
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Approaches to healing and prophylaxis of nonsteroidal anti-inflammatory drug-associated ulcers. | 2001 Jan 8 |
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Pharmacological characterization of the rat paw edema induced by Bothrops lanceolatus (Fer de lance) venom. | 2001 Jun |
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Decreased brain histamine-releasing factor protein in patients with Down syndrome and Alzheimer's disease. | 2001 Mar 2 |
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Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal. | 2001 Mar 2 |
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Peptide leucine arginine, a potent immunomodulatory peptide isolated and structurally characterized from the skin of the Northern Leopard frog, Rana pipiens. | 2001 Mar 30 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/histamine-phosphate.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17359382
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
Mon Mar 31 17:49:15 GMT 2025
by
admin
on
Mon Mar 31 17:49:15 GMT 2025
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Record UNII |
820484N8I3
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Record Status |
Validated (UNII)
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Record Version |
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34316-0
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33290-8
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C687
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127199
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2416-6
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127399
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25925-9
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WHO-ATC |
L03AX14
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C2139
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35260-9
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43577-6
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HISTAMINE
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SUB14107MIG
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
IC50
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> AGONIST |
CHO-H1 cells, histamine stimulation resulted in a concentration-dependent increase in [Ca2+]i with an EC50 of 170±30 nM.
EC50
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
MAJOR
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ACTIVE MOIETY |
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