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
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 |
|---|---|---|
| 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 |
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| H2 histamine receptor-mediated increase in intracellular Ca2+ in cultured human keratinocytes. | 1999 Sep |
|
| Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles. | 2000 Jun |
|
| Predictive markers of asthma exacerbation during stepwise dose reduction of inhaled corticosteroids. | 2001 Feb |
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| 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 |
|
| Chronic tobacco smoke exposure increases airway sensitivity to capsaicin in awake guinea pigs. | 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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| 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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| Interleukin-4-positive mast cells are highly associated with the extent of immediate allergic wheal reaction in the skin. | 2001 Jan |
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| Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma. | 2001 Jan |
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| Effects of cetirizine and epinastine on the skin response to histamine iontophoresis. | 2001 Jan |
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| Premedication with antihistamines may enhance efficacy of specific-allergen immunotherapy. | 2001 Jan |
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| Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s). | 2001 Jan |
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| Spinothalamic lamina I neurons selectively sensitive to histamine: a central neural pathway for itch. | 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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| Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate. | 2001 Jan |
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| The rat H3 receptor: gene organization and multiple isoforms. | 2001 Jan 12 |
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| Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
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| Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity. | 2001 Jan 8 |
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| Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin. | 2001 Mar |
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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
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.
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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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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
