U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of HISTAMINE

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)

HIDE SMILES / InChI

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
HISTAMINE PHOSPHATE

Approved Use

Indications 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 Date

-9.6845758E11
Primary
Unknown

Approved Use

Unknown
Diagnostic
HISTAMINE PHOSPHATE

Approved Use

Histamine 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 Date

-9.6845758E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
1877 nM × min
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12 min
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

Doses

DosePopulationAdverse 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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[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
H2 histamine receptor-mediated increase in intracellular Ca2+ in cultured human keratinocytes.
1999 Sep
Distinct pharmacology of rat and human histamine H(3) receptors: role of two amino acids in the third transmembrane domain.
2000 Dec
Possible contribution of stem cell factor in psoriasis vulgaris.
2000 Dec
Cloning of rat histamine H(3) receptor reveals distinct species pharmacological profiles.
2000 Jun
Histamine up-regulates phosphodiesterase 4 activity and reduces prostaglandin E2-inhibitory effects in human neutrophils.
2000 Nov
Histamine alters gene expression in cultured human nasal epithelial cells.
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
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.
2001 Feb
The activation of synovial mast cells: modulation of histamine release by tryptase and chymase and their inhibitors.
2001 Feb 2
Involvement of central histaminergic neurons in polypnea induced by hyperthermia in rabbits.
2001 Feb 2
Altered processing of fibronectin in mice lacking heparin. a role for heparin-dependent mast cell chymase in fibronectin degradation.
2001 Feb 9
Comparison of montelukast and fexofenadine for chronic idiopathic urticaria.
2001 Jan
Urticaria induced by cetirizine.
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
Management of severe gastroesophageal reflux disease.
2001 Jan
Role of kinins in seasonal allergic rhinitis: icatibant, a bradykinin B2 receptor antagonist, abolishes the hyperresponsiveness and nasal eosinophilia induced by antigen.
2001 Jan
Allergic asthma induced in rhesus monkeys by house dust mite (Dermatophagoides farinae).
2001 Jan
Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s).
2001 Jan
Spinothalamic lamina I neurons selectively sensitive to histamine: a central 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
Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate.
2001 Jan
In vitro catabolism of histidine by mixed rumen bacteria and protozoa.
2001 Jan
Signaling pathways leading to the induction of ornithine decarboxylase: opposite effects of p44/42 mitogen-activated protein kinase (MAPK) and p38 MAPK inhibitors.
2001 Jan 1
Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients.
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
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
Questions regarding future research on aspirin and the gastrointestinal tract.
2001 Jan 8
Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity.
2001 Jan 8
Approaches to healing and prophylaxis of nonsteroidal anti-inflammatory drug-associated ulcers.
2001 Jan 8
Sunlight, immunosuppression and skin cancer: role of histamine and mast cells.
2001 Jan-Feb
Pharmacological characterization of the rat paw edema induced by Bothrops lanceolatus (Fer de lance) venom.
2001 Jun
Interactions of inflammatory mediators stimulating release of calcitonin gene-related peptide, substance P and prostaglandin E(2) from isolated rat skin.
2001 Mar
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.
2001 Mar 2
Extracts of ECL-cell granules/vesicles and of isolated ECL cells from rat oxyntic mucosa evoke a Ca2+ second messenger response in osteoblastic cells.
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
Patents

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 Wed Jul 05 22:42:33 UTC 2023
Edited
by admin
on Wed Jul 05 22:42:33 UTC 2023
Record UNII
820484N8I3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HISTAMINE
HSDB   MART.   MI   VANDF   WHO-DD  
Systematic Name English
ERGOTIDINE
Common Name English
ERGAMINE
Common Name English
NSC-33792
Code English
Histamine [WHO-DD]
Common Name English
HISTAMINE [MI]
Common Name English
5-IMIDAZOLEETHYLAMINE
Systematic Name English
HISTAMINE [MART.]
Common Name English
1H-IMIDAZOLE-4-ETHANAMINE
Systematic Name English
HISTAMINE [VANDF]
Common Name English
.BETA.-AMINOETHYLGLYOXALINE
Common Name English
4-IMIDAZOLEETHYLAMINE
Systematic Name English
.BETA.-AMINOETHYLIMIDAZOLE
Systematic Name English
2-(4-IMIDAZOLYL)ETHYLAMINE
Systematic Name English
HISTAMINE [HSDB]
Common Name English
Classification Tree Code System Code
LOINC 34316-0
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 33290-8
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 25439-1
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 2417-4
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 34317-8
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
NCI_THESAURUS C687
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
FDA ORPHAN DRUG 127199
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 2416-6
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
FDA ORPHAN DRUG 127399
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 13755-4
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 13756-2
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 9410-2
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 2415-8
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 25925-9
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
WHO-ATC L03AX14
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
NCI_THESAURUS C2139
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 35260-9
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 43577-6
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
LOINC 44371-3
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C73238
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
NSC
33792
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
FDA UNII
820484N8I3
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
DRUG BANK
DB05381
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-100-6
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
CAS
51-45-6
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
WIKIPEDIA
HISTAMINE
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
MESH
D006632
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
DRUG CENTRAL
1375
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
MERCK INDEX
M6026
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY Merck Index
PUBCHEM
774
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
CHEBI
18295
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
CHEBI
58432
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023125
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
HSDB
3338
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
SMS_ID
100000089506
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
DAILYMED
820484N8I3
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
RXCUI
5333
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY RxNorm
EVMPD
SUB14107MIG
Created by admin on Wed Jul 05 22:42:33 UTC 2023 , Edited by admin on Wed Jul 05 22:42:33 UTC 2023
PRIMARY
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