H7125

Sigma-Aldrich

Histamine

≥97.0%

Synonym(s):
2-(4-Imidazolyl)ethylamine
Empirical Formula (Hill Notation):
C5H9N3
CAS Number:
Molecular Weight:
111.15
Beilstein/REAXYS Number:
2012
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

assay

≥97.0%

bp

167 °C/0.8 mmHg (lit.)

mp

83-84 °C (lit.)

storage temp.

−20°C

SMILES string

NCCc1cnHcn1

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

Gene Information

human ... CA1(759), CA2(760), HRH1(3269), HRH2(3274), HRH3(11255), HRH4(59340)
rat ... Hrh1(24448), Hrh3(85268)

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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

Packaging

1, 5, 25 g in glass bottle

Biochem/physiol Actions

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.
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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

22-36/37/38-42/43

Safety Statement

22-26-36/37

RIDADR

UN 2811 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Histamine in the nervous system
Haas HL, et al.
Physiological Reviews, 88(3), 1183-1241 (2008)
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)
Maikel Wijtmans et al.
Journal of medicinal chemistry, 54(6), 1693-1703 (2011-02-26)
The histamine H(3) (H(3)R) and H(4) (H(4)R) receptors attract considerable interest from the medicinal chemistry community. Given their relatively high homology yet widely differing therapeutic promises, ligand selectivity for the two receptors is crucial. We interrogated H(4)R/H(3)R selectivities using ligands...
Surfactants attenuate gas embolism-induced thrombin production
Eckmann DM and Diamond SL
Anesthesiology, 100(1), 77-84 (2004)
Protocols
HPLC Analysis of Biogenic Amines on Ascentis<sup>®</sup> RP-Amide
Read More

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