2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE
Histamine dihydrochloride
CAS: 56-92-8
Molecular Formula: C5H11Cl2N3
2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE - Names and Identifiers
| Name | Histamine dihydrochloride |
| Synonyms | histamine dihcl TIMTEC-BB SBB003722 HISTAMINE DICHLORHYDRATE Histamine dihydrochloride Histamine-alpha,alpha,??d4?HCl)2 2-(1H-IMIDAZOL-4-YL)-ETHYLAMINE 2HCL 1H-IMIDAZOLE-4-ETHANAMINE DIHYDROCHLORIDE 2-imidazol-4-ylethylamine dihydrochloride 2-[4-IMIDAZOYL]-ETHYLAMINE DIHYDROCHLORIDE 2-(4-Imidazolyl)ethylamine dihydrochloride 2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE 2-(1H-Imidazol-4-yl)ethylamine dihydrochloride |
| CAS | 56-92-8 |
| EINECS | 200-298-4 |
| InChI | InChI=1/C5H9N3.ClH/c6-2-1-5-3-7-4-8-5;/h3-4H,1-2,6H2,(H,7,8);1H/p-1 |
| InChIKey | PPZMYIBUHIPZOS-UHFFFAOYSA-N |
2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE - Physico-chemical Properties
| Molecular Formula | C5H11Cl2N3 |
| Molar Mass | 184.07 |
| Melting Point | 249-252°C(lit.) |
| Water Solubility | SOLUBLE |
| Solubility | H2O: 0.1g/mL, clear, colorless |
| Appearance | White Crystals |
| Color | white to off-white |
| Merck | 14,4719 |
| BRN | 3624116 |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| MDL | MFCD00012703 |
| Use | The natural isomer of the direct precursor of dopamine (dopamine), the product of tyrosine hydroxylase |
| In vitro study | Histamine inhibits the production of ROS through the type 2 Histamine receptor (H2 receptor). Histamine inhibits the production and release of reactive oxygen species (ROS) in monocytes/macrophages (MO) during burst respiration. Histamine and interleukin-2 (IL-2) act synergistically to activate the cytotoxicity of NK cells (NKCC). Histamine in combination with IL-2 can improve response rates and disease-free survival by protecting cells of the immune system from damage by oxidative stress and inducing innate endogenous immune cell toxicity. |
| In vivo study | In a rat model of early alcoholic liver injury, Histamine treatment (0.5 mg/kg or 5.0 mg/kg twice daily) prevented liver injury, normalized serum transaminase levels, and significantly reduce the proportion of liver pathology. The protective effect of Histamine was blocked by ranitidine (10 mg/kg) and H2 receptor antagonists, suggesting that histamine effects are mediated primarily through H2 receptors. In the nucleus accumbens of male rats, Histamine (30 picograms/rat, ICV) increased both the accumulation of 3,4-dihydroxyphenylalanine and the concentration of 3,4-dihydroxyphenylalanine, and the effect was not affected by the H2 antagonist zolantidine, suggesting that histamine stimulates brain limbic DA neurons through its action on H1 receptors. Histamine (0.5 mg/kg S.C.) reduced liver tumor weight by 46% and subcutaneous tumor weight by 41% compared to rats injected subcutaneously with normal saline. The antitumor effect of subcutaneous histamine injection was inhibited by ranitidine (50 mg/kg, subcutaneously) in rat malignancies. In Sprague-Dawley rats, Histamine (1000 mg/kg, S.C.) showed acute tissue damage after 24 h and pathological inflammation at the injection site on days 5 and 28. In male Sprague-Dawley rats, Histamine (1000 mg/kg, subcutaneously) resulted in a C max of 167 mM, a t max of 0.5 H, a t 1/2 of 0.95,AUC is 186 mmol-h/L. |
2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R42/43 - May cause sensitization by inhalation and skin contact. R42 - May cause sensitization by inhalation R22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37 - Wear suitable gloves. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | 3335 |
| WGK Germany | 2 |
| RTECS | MS1575000 |
| FLUKA BRAND F CODES | 1-8-9 |
| TSCA | Yes |
| HS Code | 29332900 |
| Hazard Class | IRRITANT |
2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE - Reference
| Reference Show more | 1. Wu Xiaohe, Geng Xiaojie, Zhang Jianxu, etc. Study on microbiology and physicochemical properties of Huanghua shrimp paste [J]. Food Research and Development, 2019, v.40;No.361(12):83-89. 2. [IF = 0.868] Zhang Y. C. et al."Aerobic oxidation of alcohol by copper(I)/benzoxazine ligand/TEMPO under mild and base-free conditions." Russ J Gen Chem . 2015 Aug;85(8):1965-1972 |
2-(1H-IMIDAZOL-4-YL)ETHYLAMINE DIHYDROCHLORIDE - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Application | histamine dihydrochloride for sustained remission and prevention of acute myeloid leukemia (AML) relapse after first remission treatment in adult patients. The drug reduces oxygen production from phagocytic cells, inhibits nicotinamide adenine dinucleotide phosphate oxidase and prevents interleukin-2 from activating NK cells and T cells. Histamine dihydrochloride injection is approved for marketing on the basis that its combination with interleukin-2 in complete remission significantly reduces relapse in AML patients. |
| preparation | a method for the synthesis of histamine dihydrochloride, the specific steps are as follows: to be equipped with mechanical stirring, the 200ml flask of the thermometer was charged with 15g of L-histidine, 1.5g of cuprous bromide, 4ml of p-methyl acetophenone and 120ml of methyl cyclohexanol, evacuated and filled with nitrogen to protect from light. The mixture was heated to 100-110 °c for 10 hours. The temperature is lowered to below 30 ° C., hydrogen chloride gas is introduced, the temperature is controlled to below 30 ° C. By using an ice bath, and the gas is introduced for 2-3 hours. The solid was filtered and washed with dichloromethane, and the filter cake was dried under vacuum for 4 hours to give an off-white solid. The solid was dissolved in 85% methanol solution, and hydrogen chloride gas was introduced twice with stirring, and the temperature was controlled to be below 30 ° C. By using an ice bath. After completion of the reaction, White Heron Z activated carbon was added to decolorize, and the filtrate was cooled and crystallized after filtration. The solid was suction-filtered and vacuum-dried to obtain 4.11g of a white solid in a yield of 23%. Related substances <0.2, single impurity <0.07%. |
| biological activity | Histamine 2HCl is an organic nitrogen compound, it acts on target cells in the mammalian brain by stimulation of histamine 1/2. |
| Target | Value |
| Use | A Biochemical reagent used as a substrate for the determination of histaminase. As a pharmaceutical intermediate, it is used for pharmaceutical manufacturing and other purposes. natural isomer of the direct precursor of dopamine, product of tyrosine hydroxylase |
Last Update：2024-04-10 22:29:15
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