HISTAMINE DIHYDROCHLORIDE

US Approved Allergenic Extract (1995)

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H9N3.2ClH
Molecular Weight	184.067
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.NCCC1=CNC=N1

InChI

InChIKey=PPZMYIBUHIPZOS-UHFFFAOYSA-N

InChI=1S/C5H9N3.2ClH/c6-2-1-5-3-7-4-8-5;;/h3-4H,1-2,6H2,(H,7,8);2*1H

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084539 | https://www.drugs.com/pro/histamine-phosphate.html | https://www.drugs.com/mmx/histamine-phosphate.html

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16648669	Agonist 2678
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084539	Agonist 2678
Histamine H3 receptor 44 Target ID: CHEMBL264 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17652997	Agonist 2678
Histamine H4 receptor 20 Target ID: CHEMBL3759 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26084539	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Allergenic skin 4 Sources: https://www.drugs.com/pro/histamine-phosphate.html	Diagnostic	Not Provided 504	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 1939
Multiple sclerosis 104 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20493888	Primary	Basic research	Unknown Approved Use Unknown
Gastric acid secretory 4 Sources: https://www.drugs.com/mmx/histamine-phosphate.html	Diagnostic	Approved 8429	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 1939

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/16695374	unhealthy n = 4 Health Status: unhealthy Condition: asthma Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/16695374	Sources: https://pubmed.ncbi.nlm.nih.gov/16695374
0.2 mg single, intramuscular Highest studied dose Dose: 0.2 mg Route: intramuscular Route: single Dose: 0.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/16695374	unhealthy n = 1 Health Status: unhealthy Condition: asthma Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/16695374	Sources: https://pubmed.ncbi.nlm.nih.gov/16695374

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCT2 355 OCT3 80

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT2 355	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/jphs/advpub/0/advpub_0_0604270010/_article/-char/ja/ Page: -	yes
OCT3 80	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/jphs/advpub/0/advpub_0_0604270010/_article/-char/ja/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY557484	https://www.001chemical.com/chem/51-45-6
3B Scientific (Wuhan) Corp	3B3-033520	http://www.3bsc.com/index/pro_info.php?id=54784
AA Blocks	AA0037B9	http://www.aablocks.com/goods/Goods/detail?id=AA0037B9
AHH Chemical co.,ltd	MB-01356	http://www.ahhchemical.com/product/MB-01356.html
AHH Chemical co.,ltd	MT-52563	http://www.ahhchemical.com/product/MT-52563.html
AK Scientific, Inc. (AKSCI)	Y9749	http://www.aksci.com/item_detail.php?cat=Y9749
Aaron Chemicals	AR003831	http://www.aaronchem.com/51-45-6
AbMole Bioscience	M5692	http://www.abmole.com/products/histamine.html
Acadechem	ACDS-017396	http://www.acadechemical.com/product/92095
Accela ChemBio Inc	SY041787	http://www.accelachem.com/cn/search.html?keyword=SY041787&attname=GoodsCode
Achemo Scientific Limited	AC-45306	http://www.achemo.com/search/?Keyword=51-45-6
Achemtek	0104-056461	http://www.achemtek.com/51-45-6
Acros Organics	AC411710010	https://www.fishersci.com/shop/products/histamine-97-acros-organics/AC411710010
Acros Organics	AC411710050	https://www.fishersci.com/shop/products/histamine-97-acros-organics/AC411710050
Acros Organics	AC411710250	https://www.fishersci.com/shop/products/histamine-97-acros-organics/AC411710250
Alfa Chemistry	AP51456-A	https://reagents.alfa-chemistry.com/product/histamine-cas-51-45-6-12315.html
Alfa Chemistry	AP51456-B	https://reagents.alfa-chemistry.com/product/histamine-free-base-cas-51-45-6-cas-51-45-6-12316.html
Alfa Chemistry	51-45-6	https://www.alfa-chemistry.com/histamine-cas-51-45-6-item-292336.htm
Alichem	69004288	http://www.alichem.com/en/products/65592-96-3.html
Alinda	ALBB-005968	http://alinda.ru/finechem_en_.html?i=ALBB-005968
Ambeed	A804010	https://www.ambeed.com/products/51-45-6.html
Ambinter	Amb1101977	http://www.ambinter.com/reference/1101977
Angene	AGN-PC-007FY2	http://www.angenechemical.com/productshow/AGN-PC-007FY2.html
Angene	AGN-PC-0TH9T7	http://www.angenechemical.com/productshow/AGN-PC-0TH9T7.html
Anward	ANW-50461	http://www.anward.com/pro_result/36912
Aurora Fine Chemicals LLC	A00.704.248	http://online.aurorafinechemicals.com/info?ID=A00.704.248
Aurora Fine Chemicals LLC	K01.795.228	http://online.aurorafinechemicals.com/info?ID=K01.795.228
Aurum Pharmatech LLC	C-5322	http://www.Aurumpharmatech.com/Product/ProductDetails/C_5322
Avantor Inc	101186-436	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101186-436
BLD Pharm	BD41747	http://www.bldpharm.com/products/51-45-6.html
BLD Pharm	BD61796	http://www.bldpharm.com/products/65592-96-3.html
BOC Sciences	344299-48-5	https://isotope.bocsci.com/product/histamine-d4-dihydrochloride-cas-344299-48-5-110348.html
BioCrick	BCN2188	http://www.biocrick.com/Histamine-BCN2188.html
BioSynth	J-505349	https://www.biosynth.com/en/products/all-products/products/J-505349.html
Boerchem	BC205752	http://www.boerchem.com/?product_34681.html
BroadPharm	BP-11484	http://www.broadpharm.com/products/Amines/BP-11484/
CSNpharm	CSN16747	https://www.csnpharm.com/products/histamine.html
Calbiochem	3779	http://www.emdbiosciences.com/product/3779
Chem Scene	CS-4697	http://www.chemscene.com/51-45-6.html
ChemFaces	CFN90029	http://www.chemfaces.com/natural/Histamine-CFN90029.html
ChemMol	30102836	http://www.chemmol.com/chemmol/30102836.html
ChemMol	44002277	http://www.chemmol.com/chemmol/44002277.html
ChemMol	49403308	http://www.chemmol.com/chemmol/49403308.html
ChemMol	49417190	http://www.chemmol.com/chemmol/49417190.html
ChemMol	49425866	http://www.chemmol.com/chemmol/49425866.html
Chemenu	CM117809	http://www.chemenu.com/products/CM117809
Chemspace	CSSB00000756591	https://chem-space.com/CSSB00000756591
Clearsynth	CS-M-25829	https://www.clearsynth.com/en/CSM25829.html
EMD Millipore	3779	http://www.emdbiosciences.com/product/3779
Finetech	FT-0627839	http://www.finetechnology-ind.com/prod/detail/pub/51-45-6.html
Glentham Life Sciences	GL9196	http://www.glentham.com/products/product/GL9196/
Hairui	HR122599	http://www.hairuichem.com/en/product/51-45-6.html
Lab Network	LN00011223	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00011223
Matrix Scientific	133714	https://www.matrixscientific.com/133714.html
MedChem Express	HY-B1204	https://www.medchemexpress.com/Histamine.html
Molcore	MC557484	https://www.molcore.com/product/51-45-6
MuseChem	I003852	https://www.musechem.com/product/I003852.html
OChem	11930	http://www.ocheminc.com/index.php?act=psearch&pid=056H928
OChem	3670	http://www.ocheminc.com/index.php?act=psearch&pid=714I940
Oakwood	78943	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64117&ExtHyperLink=1
Otava	2816948	https://search.otavachemicals.com/#!/search?query=2816948&type=code&base=dbb
Parchem	Histamine	http://www.parchem.com/chemical-supplier-distributor/Histamine-029572.aspx
Parchem	29572	https://www.parchem.com/chemical-supplier-distributor/Histamine-029572.aspx
Renno Tech	RP00535	http://www.rennotech.com/product_show.asp?id=6925
Selleck Chemicals	S3968	http://www.selleckchem.com/products/histamine.html
Sigma-Aldrich	53290_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/53290?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	59964_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/59964?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0001779_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0001779?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	H7125_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/h7125?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	V900396_VETEC	https://www.sigmaaldrich.com/catalog/product/vetec/v900396?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S001739	http://www.sinfoobiotech.com/product/1005137
Smolecule	S590017	https://www.smolecule.com/products/s590017
THE BioTek	bt-301933	https://www.thebiotek.com/product/others/bt-301933
VladaChem	VL270045-1G	https://www.vladachem.com/product.php?products=51-45-6
Yuhao Chemical	HL1018	http://www.chemyuhao.com/51-45-6.html
abcr GmbH	AB349089	http://www.abcr.com/shop/en/AB349089
abcr GmbH	AB511890	http://www.abcr.com/shop/en/AB511890
eNovation Chemicals	D382889	http://www.enovationchem.com/productDetails.asp?productID=D382889
eNovation Chemicals	D914693	https://www.enovationchem.com/ProductDetails.asp?ProductID=D914693
eNovation Chemicals	K66466	https://www.enovationchem.com/ProductDetails.asp?ProductID=K66466
eNovation Chemicals	Y1043716	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1043716
iChemical	EBD6913	http://www.ichemical.com/products/51-45-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-4970362785	https://mcule.com/MCULE-4970362785/

PubMed

Title	Date	PubMed
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	10051702
Involvement of glutamate in transmission of afferent constrictive inputs from the airways to the nucleus tractus solitarius in ferrets.	2000 Apr 12	10742536
Identification of a histamine H(3)-like receptor in the zebrafish (Danio rerio) brain.	2000 Aug	10899947
Possible contribution of stem cell factor in psoriasis vulgaris.	2000 Dec	11084298
Histamine H(3) receptors depress synaptic transmission in the corticostriatal pathway.	2001	11077076
Predictive markers of asthma exacerbation during stepwise dose reduction of inhaled corticosteroids.	2001 Feb	11179114
Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial.	2001 Feb	11174228
No correlation between wine intolerance and histamine content of wine.	2001 Feb	11174207
Acquisition and alteration of adhesion molecules during cultured human mast cell differentiation.	2001 Feb	11174197
Inhibitory action of water soluble fraction of Terminalia chebula on systemic and local anaphylaxis.	2001 Feb	11167031
Chronic tobacco smoke exposure increases airway sensitivity to capsaicin in awake guinea pigs.	2001 Feb	11160071
A human tissue-engineered vascular media: a new model for pharmacological studies of contractile responses.	2001 Feb	11156967
Ontogeny of modulatory inputs to motor networks: early established projection and progressive neurotransmitter acquisition.	2001 Feb 15	11160402
The activation of synovial mast cells: modulation of histamine release by tryptase and chymase and their inhibitors.	2001 Feb 2	11166285
Food-deprived activity stress decreased the activity of the histaminergic neuron system in rats.	2001 Feb 9	11164807
Comparison of montelukast and fexofenadine for chronic idiopathic urticaria.	2001 Jan	11176678
Preclinical profile of the monodisperse iodinated macromolecular blood pool agent P743.	2001 Jan	11176260
Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis.	2001 Jan	11167952
The treatment of rhinovirus infections: progress and potential.	2001 Jan	11166856
Inhibition by glucocorticoids of the mast cell-dependent weal and flare response in human skin in vivo.	2001 Jan	11156588
Effect of the long-acting tachykinin NK(1) receptor antagonist MEN 11467 on tracheal mucus secretion in allergic ferrets.	2001 Jan	11156577
Effects of cetirizine and epinastine on the skin response to histamine iontophoresis.	2001 Jan	11154865
Acidification of formula reduces bacterial translocation and gut colonization in a neonatal rabbit model.	2001 Jan	11150438
Regulatory effect of histamine H1 receptor antagonist on the expression of messenger RNA encoding CC chemokines in the human nasal mucosa.	2001 Jan	11150001
Role of kinins in seasonal allergic rhinitis: icatibant, a bradykinin B2 receptor antagonist, abolishes the hyperresponsiveness and nasal eosinophilia induced by antigen.	2001 Jan	11149999
Premedication with antihistamines may enhance efficacy of specific-allergen immunotherapy.	2001 Jan	11149995
Expression and biological significance of Ca2+-activated ion channels in human keratinocytes.	2001 Jan	11149902
Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s).	2001 Jan	11137352
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.	2001 Jan	11133355
Identification of rat H3 receptor isoforms with different brain expression and signaling properties.	2001 Jan	11125017
delta-opioid receptors inhibit neurogenic intestinal secretion evoked by mast cell degranulation and type I hypersensitivity.	2001 Jan 1	11108937
Luminal Nalpha-methyl histamine stimulates gastric acid secretion in duodenal ulcer patients via releasing gastrin.	2001 Jan 26	11165229
Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity.	2001 Jan 8	11165994
Approaches to healing and prophylaxis of nonsteroidal anti-inflammatory drug-associated ulcers.	2001 Jan 8	11165992
Complement-dependent immune complex-induced bronchial inflammation and hyperreactivity.	2001 Mar	11159035
Decreased brain histamine-releasing factor protein in patients with Down syndrome and Alzheimer's disease.	2001 Mar 2	11172935
Glycine receptor mediated responses in rat histaminergic neurons.	2001 Mar 2	11172926
Correlation between neutral endopetidase (NEP) 3.4.24.11 in serum and the degree of the bronchial hyperreactivity.	2001 Mar 2	11164954
Regulation of tight junction permeability and occludin phosphorylation by Rhoa-p160ROCK-dependent and -independent mechanisms.	2001 Mar 30	11139571
Transcriptional activation of the rat vesicular monoamine transporter 2 promoter in gastric epithelial cells: regulation by gastrin.	2001 Mar 9	11113118

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 17:17:19 GMT 2023` Edited by `admin` on `Fri Dec 15 17:17:19 GMT 2023`
Record UNII	3POA0Q644U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HISTAMINE DIHYDROCHLORIDE

Official Name

English

HISTAMINE DIHYDROCHLORIDE [USAN]

Common Name

English

PEREMIN

Brand Name

English

HISTAMINE HYDROCHLORIDE [MART.]

Common Name

English

1H-IMIDAZOLE-5-ETHANAMINE, HYDROCHLORIDE (1:2)

Systematic Name

English

Histamine hydrochloride [WHO-DD]

Common Name

English

HISTAMINE DIHYDROCHLORIDE [USP-RS]

Common Name

English

2-(4-IMIDAZOLYL)ETHYLAMINE DIHYDROCHLORIDE

Systematic Name

English

1H-IMIDAZOLE-4-ETHANAMINE DIHYDROCHLORIDE

Systematic Name

English

CEPLENE

Brand Name

English

HISTAMINE DIHYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

HISTAMINE DIHYDROCHLORIDE [EMA EPAR]

Common Name

English

ALLERGEN SCRATCH EXTRACT POSITIVE CONTROL 'TORII' HISTAMINE DIHYDROCHLORIDE

Brand Name

English

HISTAMINUM HYDROCHLORICUM [HPUS]

Common Name

English

HISTAMINE DIHYDROCHLORIDE [MI]

Common Name

English

HISTAMINUM HYDROCHLORICUM

Common Name

English

NSC-257873

Code

English

HISTAMINE HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

EMA ASSESSMENT REPORTS

CEPLENE (AUTHORIZED: LEUKEMIA, MYELOID, ACUTE)