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53300

Sigma-Aldrich

Histamine dihydrochloride

≥99.0% (AT)

Synonym(s):
2-(4-Imidazolyl)ethylamine dihydrochloride
Empirical Formula (Hill Notation):
C5H9N3 · 2HCl
CAS Number:
Molecular Weight:
184.07
Beilstein:
3624116
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.77

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)

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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.

Packaging

1, 5, 25 g in glass bottle

Biochem/physiol Actions

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

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Yogesh Dahiya et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(40), 7934-7946 (2019-08-16)
Memory formation is crucial for the survival of animals. Here, we study the effect of different crh-1 [Caenorhabditis elegans homolog of mammalian cAMP response element binding protein 1 (CREB1)] isoforms on the ability of C. elegans to form long-term memory...
Isabel Sanz-Vicente et al.
Analytical and bioanalytical chemistry, 412(18), 4261-4271 (2020-05-14)
Diamino-oxidase (DAO), horseradish peroxidase (HRP), and tetramethylbenzidine (TMB) have been immobilized into cellulose to obtain circular cellulose test supports (CCTSs) for the determination of cadaverine (Cad) and putrescine (Put). During the enzymatic reaction, TMB is oxidized and a blue spot...
Kevin B Freeman et al.
Psychopharmacology, 231(12), 2395-2403 (2014-01-09)
Recent research has demonstrated that the drug, histamine, can function as a punisher of cocaine self-administration. However, little is known about how drug punishers affect the maximum reinforcing effectiveness of drugs as reinforcers. The goal of the present study was...

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