Histamine CAS 51-45-6
Introduction：Basic information about Histamine CAS 51-45-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Histamine Basic information
| Product Name: | Histamine |
| Synonyms: | 2-(4-Imidazolyl)ethanamine;β-Aminoethylglyoxaline;1H-Imidazole-4-ethanamine (9CI);Eramine;Histamine (8CI);4-(2-aminoethyl)-imidazol;4-Imidazoleethylamine;5-Imidazoleethylamine |
| CAS: | 51-45-6 |
| MF: | C5H9N3 |
| MW: | 111.15 |
| EINECS: | 200-100-6 |
| Product Categories: | Bioactive Small Molecules;Building Blocks;C3 to C8;Cell Biology;Chemical Synthesis;H;Heterocyclic Building Blocks;Imidazoles;MI;Halogenated Heterocycles ,Quinoxalines ,Quinolines ,Quinazolines;Inhibitors |
| Mol File: | 51-45-6.mol |
Histamine Chemical Properties
| Melting point | 83-84 °C (lit.) |
| Boiling point | 167 °C/0.8 mmHg (lit.) |
| density | 0.9902 (rough estimate) |
| refractive index | 1.4690 (estimate) |
| storage temp. | -20°C |
| solubility | DMSO: 20 mg/ml; Ethanol: 10 mg/ml; PBS (pH 7.2): 10 mg/ml |
| form | Solid |
| pka | 6.04(at 25℃) |
| color | White to light yellow |
| Water Solubility | Soluble in water, alcohol, and hot chloroform. |
| Merck | 13,4739 |
| BRN | 2012 |
| Stability: | Hygroscopic |
| InChI | 1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8) |
| InChIKey | NTYJJOPFIAHURM-UHFFFAOYSA-N |
| SMILES | NCCc1c[nH]cn1 |
| LogP | -0.700 |
| CAS DataBase Reference | 51-45-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Histamine(51-45-6) |
| EPA Substance Registry System | Histamine (51-45-6) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38-42/43 |
| Safety Statements | 22-26-36/37 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | MS1050000 |
| F | 3-10-23 |
| TSCA | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29332900 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Eye Irrit. 2 Resp. Sens. 1 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 51-45-6(Hazardous Substances Data) |
| Toxicity | LD50 i.p. in mice: 2020 mg/kg (Nagai) |
| Chemical Properties | White to slightly yellow powder |
| History | Histamine is an important protein involved in many allergic reactions. Allergies are caused by an immune response to a normally innocuous substance (i.e. pollen, dust) that comes in contact with lymphocytes specific for that substance, or antigen. The history of histamine and the development of antihistamines have been reviewed in [Drugs of Today (1986) and the Journal of Allergy & Clinical Immunology]. Histamine was the first to be characterized of a series of biogenic amines that are released in the inflammatory process. As early as 1910, it was shown that histamine caused constriction of isolated guinea pig ileum and, subsequently, it was found that histamine induced a shock-like syndrome. In 1927 the presence of histamine in normal tissues was demonstrated. Attempts to reduce histamine manifestations led to the report, in 1933, that certain phenolic ethers inhibited histamine action. Toxicity precluded clinical use. In 1942 phenbenzamine (Antergan), C17H22N2, was the first antihistamine to be successfully used in humans. In 1966, the name H1 was proposed for receptors blocked by the at that time known antihistamines. It was also speculated that the other actions of histamine were likely to be mediated by other histamine receptors. The existence of the H2 receptor was accepted in 1972 and the H3 receptor was recognized in rat brain in 1983. H3 receptors in the brain appear to be involved in the feedback control of both histamine synthesis and release, whereas release of various other neurotransmitters, eg, serotinin (5-HT), dopamine, noradrenaline, and acetylcholine, is also modulated. H3 receptor effects have also been demonstrated in various peripheral tissues and H3 agonists and antagonists are undergoing intensive study for therapeutic applications. |
| Uses | Histamine inhibits the synthesis of IL-2 and γ-IFN in peripheral blood mononuclear cells and lipopolysaccharide-induced synthesis of TNF-α in monocytes via H2?receptor activation. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. |
| Uses | H1&2 agonist, edema induction, gastric secretion stimulant |
| Definition | ChEBI: A member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group. |
| Indications | Sinus problems, hay fever, bronchial asthma, hives,eczema, contact dermatitis, food allergies, and reactionsto drugs are all allergic reactions associated with the releaseof histamine and other autocoids, such as serotonin,leukotrienes, and prostaglandins. Histamine releaseis frequently associated with various inflammatorystates and may be increased in urticarial reactions, mastocytosis,and basophilia. Histamine also acts as a neurotransmitterin the central nervous system (CNS).Upon release from its storage sites, histamine exerts effectsranging from mild irritation and itching to anaphylacticshock and eventual death. |
| Biosynthesis | Virtually all of the histamine found in individual organsand tissues is synthesized locally and stored in subcellularsecretory granules. Within the tissues, the mast cellsare the principal sites of storage; in the blood, the basophils serve this function. Histamine is also present inneurons of the CNS, where it acts as a neurotransmitter. Histamine is synthesized from the amino acid histidineby an action of the enzyme histidine decarboxylase. Following synthesis, histamine is either rapidlyinactivated or stored in the secretory granules ofmast cells and basophils as an inactive complex withproteases and heparin sulfate or chondroitin sulfate. |
| Biological Functions | Histamine occurs in the brain, particularly in certainhypothalamic neurons, and evidence is strong that histamineis a neurotransmitter. Distribution of histamine,its synthetic enzyme (histidine decarboxylase), andmethyl histamine (the major brain metabolite) is notuniform. Possible roles for histamine in the regulationof food and water intake, thermoregulation, hormonerelease, and sleep have been suggested. |
| General Description | Histamine is a neurotransmitter produced by neurons of the posterior hypothalamus. In the brain, histamine is predominantly present in the gray matter. |
| 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. |
| Mechanism of action | Non–Antigen-Mediated Release of HistamineHistamine may be released from mast cells by mechanismsthat do not require prior sensitization of the immunesystem. Drugs, high-molecular-weight proteins,venoms, and other substances that damage or disruptcell membranes can induce the release of histamine.Any thermal or mechanical stress of sufficient intensityalso will result in histamine release. Cytotoxic compounds,may release histamine as the result of disruptionof cell membranes. |
| Pharmacology | Histamine is found in animal tissues and venoms andin many bacteria and plants.Within the human body, thelargest histamine concentrations are in the skin, lungs,and gastrointestinal mucosa, while concentrations aresmaller in almost all other organs and tissues.Histamineis present in human plasma at relatively low concentrations(usually less than 0.5 ng/mL); in contrast, wholebloodlevels can be as high as 30-fold greater. Substantialquantities of histamine are present in urine, with excretionrates varying from 10 to 40μg per 24 hours. |
| Clinical Use | Histamine has only minor uses in clinical medicine. Inthe past it was used to diagnose pernicious anemia, inwhich histamine fails to evoke the usual secretion ofgastric acid. Histamine has been used to assessbronchial hyperreactivity, although this test may bequite hazardous for asthmatics. Today the main clinicaluse of histamine is as a positive control injection for allergyskin testing. |
| Side effects | Sedation is the most frequent adverse reaction to thefirst-generation antihistamines. An additive effect onalertness and motor skills will result if alcohol or anotherdepressant is taken with these drugs. Antimuscariniceffects caused by these drugs include drymouth and respiratory passages, urinary retention, anddysuria. Nausea, vomiting, constipation or diarrhea,dizziness, insomnia, nervousness, and fatigue also havebeen reported. Drug allergy, especially after topical application,is fairly common.Tolerance to certain antihistaminesmay develop after prolonged administration.Teratogenic effects of the piperazine antihistamineshave been shown in animal studies. Epidemiological studies have not shown such an association in humans.The effects of toxic doses of first-generation antihistamines,similar to those seen following atropine administration,include excitement, hallucinations, dry mouth,dilated pupils, flushing, convulsions, urinary retention,sinus tachycardia, coma, and death. The second-generation H1-antagonists are often referredto as nonsedating antihistamines; however, dosesabove the usual therapeutic level can cause sleepinessin certain individuals.A more serious adverse effect ofsome earlier second-generation antihistamines is cardiotoxicity. |
| Synthesis | Histamine is synthesized in tissues by decarboxylation of amino acid L-histidine, a processcatalyzed by the pyridoxalphosphate-dependent enzyme L-histidinedecarboxylase.Histamine can enter the organism with food; it also can be generated by bacteria of the gastrointestinal tract. |
| Purification Methods | It crystallises from *benzene or chloroform. [Beilstein 25 I 628, 25 II 302, 25 III/IV 2049.] |
Histamine Preparation Products And Raw materials
| Raw materials | Sulfuric acid-->Benzoyl chloride-->L-Histidine |
| Preparation Products | L-Histidine-->DL-Histidine-->4-pyridin-2-yl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine(SALTDATA: H2O) |
