51-45-6 Usage
Chemical Description
Histamine is used in the synthesis of the radioiodinated derivative of DES, and DES is the compound of interest for the radioimmunoassay.
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
Different sources of media describe the Uses of 51-45-6 differently. You can refer to the following data:
1. 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.
2. 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 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.
Biosynthesis
Virtually 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 Functions
Histamine 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 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 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.
Pharmacology
Histamine 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 Use
Histamine 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 effects
Sedation 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.
Synthesis
Histamine 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 Methods
It crystallises from *benzene or chloroform. [Beilstein 25 I 628, 25 II 302, 25 III/IV 2049.]
Check Digit Verification of cas no
The CAS Registry Mumber 51-45-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 51-45:
(4*5)+(3*1)+(2*4)+(1*5)=36
36 % 10 = 6
So 51-45-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H9N3/c1-4(6)5-2-7-3-8-5/h2-4H,6H2,1H3,(H,7,8)
51-45-6Relevant articles and documents
The metabolism of histamine-beta-C.
BOUTHILLIER,GOLDNER
, p. 251 - 252 (1953)
-
-
Chang,Snell
, p. 2005,2010 (1968)
-
The intrinsic basicity of 4(5)-2′-aminoethylimidazole (histamine)
Hernández-Laguna,Abboud,Notario,Homan,Smeyers
, p. 1450 - 1454 (1993)
The gas-phase basicity (GB) of histamine (1) relative to ammonia (defined as the standard Gibbs energy change for reaction 1) has been measured by means of Fourier transform ion cyclotron resonance spectroscopy (FT-ICR): 1H+(g) + NH3(g) ? 1(g) + NH4+(g). The various tautomer/conformers of 1H+(g) were studied by means of ab initio SCF-LCAO-MO calculations at the 6-31G//6-31G level. The calculated proton affinity agrees well with that estimated from FT-ICR results. Ring protonation is slightly preferred over side-chain protonation. Chelation provides a major contribution to the stability of 1H+(g). Comparison of these results with aqueous solution data reveals dramatic differences due to solvation.
A single amino acid substitution converts a histidine decarboxylase to an imidazole acetaldehyde synthase
Takeshima, Daiki,Mori, Ayaka,Ito, Hideyuki,Komori, Hirofumi,Ueno, Hiroshi,Nitta, Yoko
, (2020)
Histidine decarboxylase (HDC; EC 4.1.1.22), an enzyme that catalyzes histamine synthesis with high substrate specificity, is a member of the group II pyridoxal 5′-phosphate (PLP) -dependent decarboxylase family. Tyrosine is a conserved residue among group II PLP-dependent decarboxylases. Human HDC has a Y334 located on a catalytically important loop at the active site. In this study, we demonstrated that a HDC Y334F mutant is capable of catalyzing the decarboxylation-dependent oxidative deamination of histidine to yield imidazole acetaldehyde. Replacement of the active-site Tyr with Phe in group II PLP-dependent decarboxylases, including mammalian aromatic amino acid decarboxylase, plant tyrosine/DOPA decarboxylase, and plant tryptophan decarboxylase, is expected to result in the same functional change, given that a Y-to-F substitution at the corresponding residue (number 260) in the HDC of Morganella morganii, another group II PLP-dependent decarboxylase, yielded the same effect. Thus, it was suggested that the loss of the OH moiety from the active-site Tyr residue of decarboxylase uniquely converts the enzyme to an aldehyde synthase.
Interaction pattern of histidine, carnosine and histamine with methylglyoxal and other carbonyl compounds
Ghassem Zadeh, Raheleh,Yaylayan, Varoujan
, (2021)
The ability of histidine to scavenge sugar-derived 1,2-dicarbonyl compounds was investigated using aqueous methanolic model systems containing histidine or histamine in the presence of glucose, methylglyoxal, or glyoxal. The samples were prepared either a
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
