Histamine

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 Structure
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
pka6.04(at 25℃)
form Solid
color White to light yellow
Water Solubility Soluble in water, alcohol, and hot chloroform.
Merck 13,4739
BRN 2012
Stability:Hygroscopic
InChIKeyNTYJJOPFIAHURM-UHFFFAOYSA-N
LogP-0.700
CAS DataBase Reference51-45-6(CAS DataBase Reference)
NIST Chemistry ReferenceHistamine(51-45-6)
EPA Substance Registry SystemHistamine (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
3-10-23
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 29332900
Hazardous Substances Data51-45-6(Hazardous Substances Data)
ToxicityLD50 i.p. in mice: 2020 mg/kg (Nagai)
MSDS Information
ProviderLanguage
4-(2-Aminoethyl)-1H-imidazole English
SigmaAldrich English
Histamine Usage And Synthesis
Chemical PropertiesWhite to slightly yellow powder
HistoryHistamine 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.
UsesH1&2 agonist, edema induction, gastric secretion stimulant
UsesHistamine 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.
IndicationsSinus problems, hay fever, bronchial asthma, hives, eczema, contact dermatitis, food allergies, and reactions to drugs are all allergic reactions associated with the release of histamine and other autocoids, such as serotonin, leukotrienes, and prostaglandins. Histamine release is frequently associated with various inflammatory states and may be increased in urticarial reactions, mastocytosis, and basophilia. Histamine also acts as a neurotransmitter in the central nervous system (CNS). Upon release from its storage sites, histamine exerts effects ranging from mild irritation and itching to anaphylactic shock and eventual death.
DefinitionChEBI: A member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group.
BiosynthesisVirtually all of the histamine found in individual organs and tissues is synthesized locally and stored in subcellular secretory granules. Within the tissues, the mast cells are the principal sites of storage; in the blood, the basophils serve this function. Histamine is also present in neurons of the CNS, where it acts as a neurotransmitter.
Histamine is synthesized from the amino acid histidine by an action of the enzyme histidine decarboxylase. Following synthesis, histamine is either rapidly inactivated or stored in the secretory granules of mast cells and basophils as an inactive complex with proteases and heparin sulfate or chondroitin sulfate.
Biological FunctionsHistamine occurs in the brain, particularly in certain hypothalamic neurons, and evidence is strong that histamine is a neurotransmitter. Distribution of histamine, its synthetic enzyme (histidine decarboxylase), and methyl histamine (the major brain metabolite) is not uniform. Possible roles for histamine in the regulation of food and water intake, thermoregulation, hormone release, and sleep have been suggested.
General DescriptionHistamine is a neurotransmitter produced by neurons of the posterior hypothalamus. In the brain, histamine is predominantly present in the gray matter.
Biochem/physiol ActionsHistamine 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 actionNon–Antigen-Mediated Release of Histamine Histamine may be released from mast cells by mechanisms that do not require prior sensitization of the immune system. Drugs, high-molecular-weight proteins, venoms, and other substances that damage or disrupt cell membranes can induce the release of histamine. Any thermal or mechanical stress of sufficient intensity also will result in histamine release. Cytotoxic compounds, may release histamine as the result of disruption of cell membranes.
PharmacologyHistamine is found in animal tissues and venoms and in many bacteria and plants.Within the human body, the largest histamine concentrations are in the skin, lungs, and gastrointestinal mucosa, while concentrations are smaller in almost all other organs and tissues.Histamine is present in human plasma at relatively low concentrations (usually less than 0.5 ng/mL); in contrast, wholeblood levels can be as high as 30-fold greater. Substantial quantities of histamine are present in urine, with excretion rates varying from 10 to 40μg per 24 hours.
Clinical UseHistamine has only minor uses in clinical medicine. In the past it was used to diagnose pernicious anemia, in which histamine fails to evoke the usual secretion of gastric acid. Histamine has been used to assess bronchial hyperreactivity, although this test may be quite hazardous for asthmatics. Today the main clinical use of histamine is as a positive control injection for allergy skin testing.
Side effectsSedation is the most frequent adverse reaction to the first-generation antihistamines. An additive effect on alertness and motor skills will result if alcohol or another depressant is taken with these drugs. Antimuscarinic effects caused by these drugs include dry mouth and respiratory passages, urinary retention, and dysuria. Nausea, vomiting, constipation or diarrhea, dizziness, insomnia, nervousness, and fatigue also have been reported. Drug allergy, especially after topical application, is fairly common.Tolerance to certain antihistamines may develop after prolonged administration. Teratogenic effects of the piperazine antihistamines have 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 referred to as nonsedating antihistamines; however, doses above the usual therapeutic level can cause sleepiness in certain individuals.A more serious adverse effect of some earlier second-generation antihistamines is cardiotoxicity.
SynthesisHistamine is synthesized in tissues by decarboxylation of amino acid L-histidine, a process catalyzed 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 MethodsIt crystallises from *benzene or chloroform. [Beilstein 25 I 628, 25 II 302, 25 III/IV 2049.]
Histamine Preparation Products And Raw materials
Raw materialsSulfuric acid-->Benzoyl chloride-->L-Histidine
Preparation ProductsL-Histidine-->DL-Histidine-->4-pyridin-2-yl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine(SALTDATA: H2O)
ethanamine HISTAMINE 1 RECEPTOR 1, RAT, 17AA NEAR CT ANTI-HISTAMINE RECEPTOR 3, N-TERMINAL L-HOMOCARNOSINE SULFATE HISTAMINE BISPHOSPHATE MONOHYDRATE H-GLY-HIS-GLY-OH 4-PREGNEN-3,20-DIONE-11ALPHA-HEMISUCCINATE-HISTAMINE HIPPURYL-HIS-LEU BZL-HIS(BZL)-OH N-OMEGA-ACETYLHISTAMINE D(+)-HISTIDINOL DIHYDROCHLORIDE L-1-Phenylethylamine 1-METHYLHISTAMINE DIHYDROCHLORIDE 1-Methyl-L-histidine N-Acetyl-L-histidine HISTAMINE ACID PHOSPHATE N-PHTHALOYL-DL-HISTIDINE DL-HISTIDINE DIHYDROCHLORIDE

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