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H7125

Sigma-Aldrich

Histamine

≥97% (TLC), powder, H₁ and H₂ histamine receptor agonist

Synonym(s):

2-(4-Imidazolyl)ethylamine

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About This Item

Empirical Formula (Hill Notation):
C5H9N3
CAS Number:
Molecular Weight:
111.15
Beilstein:
2012
EC Number:
MDL number:
UNSPSC Code:
12352116
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.77

product name

Histamine, ≥97.0%

Quality Level

Assay

≥97.0%

bp

167 °C/0.8 mmHg (lit.)

mp

83-84 °C (lit.)

storage temp.

−20°C

SMILES string

NCCc1c[nH]cn1

InChI

1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)

InChI key

NTYJJOPFIAHURM-UHFFFAOYSA-N

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General description

Histamine is a neurotransmitter produced by neurons of the posterior hypothalamus. In the brain, histamine is predominantly present in the gray matter.

Application

Histamine has been used:
  • to stimulate regulated cellular secretion
  • in reaction mixture to activate blood for assaying thrombin (factor iia) activity by fluorimetry
  • to fill the luminal side of the chamber to investigate its effects on the TJ-related barrier and the expression of TJ (tight junction) markers in the vocal fold epithelium

Biochem/physiol Actions

Endogenous H1 and H2 histamine receptor agonist; H1 activation mobilizes Ca2+; H2 activation stimulates adenylate cyclase activity in neurons; activates nitric oxide synthetase; potent vasodilator.
Histamine participates in innate and acquired immune response, mediating allergy and inflammation. It helps in intestinal muscle contraction. During anaphylactic shock histamine causes bronchial constriction. Histamine is also involved in gastric acid secretion, epithelial and endothelial barrier control.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Phospholipase D1 is specifically required for regulated secretion of von Willebrand factor from endothelial cells
Disse J, et al.
Blood, 113(4), 973-980 (2009)
Rogier A Smits et al.
Journal of medicinal chemistry, 51(8), 2457-2467 (2008-03-25)
Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H 4R) from which 2-(4-methyl-piperazin-1-yl)-quinoxaline ( 3) was identified as a new lead structure for H
Endogenous histamine facilitates long-term potentiation in the hippocampus during walking
Luo T and Leung LS
The Journal of Neuroscience, 30(23), 7845-7852 (2010)
Tight junction-related barrier contributes to the electrophysiological asymmetry across vocal fold epithelium
Zhang Q and Fisher K
PLoS ONE, 7(3), e34017-e34017 (2012)
Histamine in the nervous system
Haas HL, et al.
Physiological Reviews, 88(3), 1183-1241 (2008)

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