Histamine dihydrochloride Chemical Properties

Melting point:

249-252 °C(lit.)

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, clear, colorless

form 

powder

color 

white to off-white

Water Solubility 

SOLUBLE

Merck 

14,4719

BRN 

3624116

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

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

InChIKey

PPZMYIBUHIPZOS-UHFFFAOYSA-N

SMILES

C1(N=CNC=1)CCN.Cl.Cl

CAS DataBase Reference

56-92-8(CAS DataBase Reference)

EPA Substance Registry System

1H-Imidazole-4-ethanamine, dihydrochloride (56-92-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-42/43-42-22

Safety Statements 

22-26-36/37/39-45-37-36/37

RIDADR 

3335

WGK Germany 

2

RTECS 

MS1575000

F 

1-8-9

TSCA 

TSCA listed

HazardClass 

IRRITANT

HS Code 

29332900

Storage Class

11 - Combustible Solids

Hazard Classifications

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

MSDS

• Language:English Provider:2-(4-Imidazolyl)ethylamine dihydrochloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Histamine dihydrochloride Usage And Synthesis

Chemical Properties

white powder

Uses

Present in most mammalian tissues; primarily stored in mast cells and basophils. Exhibits multiple biological effects through at least 3 specific receptors. Induces bronchoconstriction and vasodilation; stimulates gastric acid secretion; and acts as a neurotransmitter.

Uses

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. It is a potent vasodilator and endogenous histamine receptor agonist.

Uses

Histamine dihydrochloride has been used:

• as a orthograde cotransmitter in producing excitatory postsynaptic potential (EPSP)
• to determine its level in fish using HPLC (high performance liquid chromatography)
• to assess the tracheal response to antigens in guinea-pigs

General Description

Histamine Dihydrochloride is a derivative of histamine, which is implicated in tumor cell apoptosis and prevents the relapse of acute myeloid leukemia in patients. It prevents the formation of ROS (reactive oxygen species) and inhibits the activation of T cells and natural killer cells.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Biological Activity

Endogenous agonist at histamine receptors (H 1-4 ). Released from mast cells and basophils and exhibits inflammatory, vasodilatory and bronchoconstrictory activity. Stimulates gastric acid secretion and acts as a neurotransmitter in vivo .

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.

Synthesis

A method for synthesizing histamine dihydrochloride was carried out as follows: 15 g of L-histidine, 1.5 g of cuprous bromide, 4 ml of p-methylacetophenone, and 120 ml of methylcyclohexanol were added to a 200 ml flask equipped with mechanical stirring and a thermometer, evacuated and then filled with nitrogen to protect it from light. The reaction was heated to 100-110??C for 10 hours. The temperature was lowered to below 30??C and hydrogen chloride gas was introduced, an ice bath was used to control the temperature below 30??C and the gas was introduced for 2 to 3 hours. The solid was filtered and washed with dichloromethane, and the filter cake was vacuum dried for 4 hours to obtain a white-like solid. The solid was dissolved in 85% methanol solution, and hydrogen chloride gas was introduced for the second time with stirring, and an ice bath was used to control the temperature below 30??. At the end of the reaction, Egret Z activated carbon was added to decolorize, and the filtrate was filtered to precipitate crystals at a reduced temperature. The solid was filtered and vacuum dried to obtain 4.11g of white solid with 23% yield. Related substances <0.2, single impurity <0.07%.

storage

Room temperature (desiccate)

Purification Methods

The dihydrochloride crystallises from aqueous EtOH. The phosphate (2H3PO4) [51-74-1] has m 132-133o (from H2O). [Beilstein 25 III/IV 2049.]

Histamine dihydrochloride(56-92-8)Related Product Information

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