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Merck
CN

53300

Histamine dihydrochloride

≥99.0% (AT), powder or crystals, endogenous histamine receptor agonist

Synonym(s):

2-(4-Imidazolyl)ethylamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C5H9N3 · 2HCl
CAS Number:
Molecular Weight:
184.07
NACRES:
NA.77
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352116
EC Number:
200-298-4
MDL number:
Beilstein/REAXYS Number:
3624116
Assay:
≥99.0% (AT)
Form:
powder or crystals
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Product Name

Histamine dihydrochloride, ≥99.0% (AT)

assay

≥99.0% (AT)

form

powder or crystals

ign. residue

≤0.2%

loss

≤0.2% loss on drying, 20 °C (HV)

mp

244-247 °C, 249-252 °C (lit.)

solubility

H2O: 0.1 g/mL, clear, colorless

anion traces

sulfate (SO42-): ≤200 ppm

cation traces

Ca: ≤10 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤5 mg/kg, Fe: ≤5 mg/kg, K: ≤50 mg/kg, Mg: ≤5 mg/kg, Mn: ≤5 mg/kg, Na: ≤50 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

SMILES string

Cl[H].Cl[H].NCCc1c[nH]cn1

InChI

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

InChI key

PPZMYIBUHIPZOS-UHFFFAOYSA-N

Gene Information

human ... HRH1(3269)

General description

Histamine is a hydrophilic amine derived from the decarboxylation of histidine by the enzyme L-histidine decarboxylase. Histamine has been shown to play a role in many physiological processes such as gastric secretion, neurotransmission, immune response, vasodialation, and inflammation. Additionally, studies have reported a role for histamine dihydrochloride with interleukin-2 (IL-2) in treatment of acute myeloid leukemia and in protection against alcohol-induced liver injury in rats.

Biochem/physiol Actions

Endogenous H1 and H2 histamine receptor agonist; activates nitric oxide synthetase; potent vasodilator.
Histamine dihydrochloride has been shown to activate nitric oxide synthetase and suppress or inhibit the generation of reactive oxygen species (ROS). Inhibition of ROS by histamine dihydrochloride allows activation of T cells and NK cells by IL-2. In a rat model, histamine dihydrochloride suppressed ROS generated by Kupffer cells through the H2 histamine receptor.

Other Notes

Substrate for the assay of histamine-N-methyltransferase (EC 2.1.1.8); Ion-pair extraction of histamine from biological fluids for its determination by HPLC with fluorescence detection.


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pictograms

Health hazardExclamation mark

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves



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J. Axelrod
Methods in Enzymology, 17B, 766-766 (1971)
D Tsikas et al.
Journal of chromatography, 614(1), 37-41 (1993-04-21)
A procedure for the selective ion-pair extraction of histamine from various biological fluids and tissues by using the ion-pairing agent bis(2-ethylhexyl)hydrogen-phosphoric acid has been developed. This procedure enabled routine determination of histamine in plasma, urine and tissue samples of humans
Stephen C Hornyak et al.
Inflammation, 27(5), 317-327 (2003-11-26)
Inflammation of the liver may be caused by a variety of factors that include infectious agents and toxins. Reactive oxygen species (ROS) generated by the NADPH oxidase in Kupffer cells and infiltrating leukocytes play an important role in the pathogenesis



Global Trade Item Number

SKUGTIN
W514500-10KG-K04061837521126
PHR1081-10G04061835232888
PHR1081-1G04061837883965
437379-100ML04061832118727
1477943-400MG04061838737540
W514500-1KG-K04061837521133
W514500-SAMPLE-K04061837521140
52184-1ML04061832547404
53300-5G04061835258147
53300-1G04061832559100
53300-25G04061832559117