histamine
American Heritage Dictionary:
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his·ta·mine
(hĭs'tə-mēn', -mĭn) 
n.
A physiologically active amine, C5H9N3, found in plant and animal tissue and released from mast cells as part of an allergic reaction in humans. It stimulates gastric secretion and causes dilation of capillaries, constriction of bronchial smooth muscle, and decreased blood pressure.
n.
A physiologically active amine, C5H9N3, found in plant and animal tissue and released from mast cells as part of an allergic reaction in humans. It stimulates gastric secretion and causes dilation of capillaries, constriction of bronchial smooth muscle, and decreased blood pressure.
[HIST(IDINE) + AMINE.]
histaminic his'ta·min'ic (-mĭn'ĭk) adj.Britannica Concise Encyclopedia:
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histamine
Organic compound found in nearly all animal tissues, in microorganisms, and in some plants. Its release stimulates many smooth muscles to contract, such as those in the gastrointestinal tract, uterus, and the bronchi. It causes fine blood vessels to dilate and become more permeable, causing the runny nose, watery eyes, and tissue swelling of hay fever and some other allergies. Histamine appears to have a physiological role in the body's defenses against a hostile environment, since it may be released when the body is subjected to trauma, infection, or some drugs. Under extreme circumstances, the effects of histamine lead to exaggerated responses with distressing results, as may occur in some allergic conditions ( anaphylaxis). Stinging nettles and certain insect venoms contain histamine. In humans, histamine is formed by removal of a carboxyl group from histidine. Its effects are counteracted by antihistamines.
For more information on histamine, visit Britannica.com.
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A biologically active amine that is formed by the decarboxylation of the amino acid histidine. It is widely distributed in nature and is found in plant and animal tissues as well as in insect venoms. In humans, histamine is a mediator of inflammatory reactions, and it functions as a stimulant of hydrochloric acid secretion in the stomach.
Most tissue histamine is found stored in mast cells, where it can be released by a variety of stimuli. Once released, it can cause many effects, including constriction of bronchiolar, gastrointestinal, uterine smooth muscle, and lowering of blood pressure. If histamine is released in the skin, itching, a flare (area of redness) due to vasodilation, and a wheal due to leaking of fluid into the tissue are observed. The increase in vascular permeability that permits this leakage is due to an action on the endothelial cells of postcapillary venules.
All of these actions of histamine are mediated by the activation of histamine receptors, designated either H-1 or H-2. Antihistamine drugs exert their effects by blocking the combination of histamine with these receptors. See also Antihistamine.
Histamine release can be caused by tissue injury, by physical stimuli such as cold or pressure, by drugs such as heroin, and most importantly by immunologic mechanisms. Mast cells in the skin, the lung, the nasal passages, or other sites may become sensitized to antigens such as ragweed or other pollens, and then release histamine and other biologically active substances upon exposure to them. The released histamine may then cause the effects commonly associated with allergic responses. If the allergic reaction becomes generalized and severe, life-threatening anaphylactic shock may ensue. The prompt administration of epinephrine, which exerts effects opposite to those of histamine, can be life-saving in such cases. See also Allergy; Antigen; Epinephrine; Hypersensitivity; Immunology.
Oxford Food & Nutrition Dictionary:
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histamine
The amine formed by decarboxylation of the amino acid histidine in the body, also found in small amounts in cheeses, beer, chocolate, sauerkraut, and wines. Excessive release of histamine from mast cells is responsible for many of the symptoms of allergic reactions. It also stimulates secretion of gastric acid, and administration of histamine provides a test for achlorhydria.
Oxford Food & Fitness Dictionary:
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histamine
Histamine, a chemical derived from the amino acid histidine, has been implicated in a number of disorders. It is a transmitter of nerve impulses secreted by the hypothalamus in the brain. In addition to its function in the nervous system, it is released from body tissues during allergic reactions. Release into the skin causes nettle rash; release in the lungs contributes to asthma. Certain foods, such as chocolate, fish, and strawberries may stimulate immune cells (mast cells) to secrete histamine in sensitized individuals. This may be responsible for some cases of food intolerance.
Oxford A-Z of Medicinal Drugs:
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histamine
A compound found in nearly all tissues of the body, with high concentrations in the skin, lungs, and intestines. Histamine causes dilatation of blood vessels and contraction of smooth muscle (for example in the airways) and regulates the secretion of gastric (stomach) acid. It plays an important role in inflammation and is released in large amounts after skin damage (such as that due to animal venoms). It is also released in anaphylactic reactions (see anaphylaxis) and allergic conditions, giving rise to some of the symptoms of these conditions. Histamine acts at specific sites (receptors) in the tissues, of which there are two main types, H1 receptors and H2 receptors. Antihistamines (H1-receptor antagonists) block H1 receptors in the skin, nose, and airways and are used for treating such allergic reactions as urticaria (nettle rash) and hay fever. H2-receptor antagonists block H2 receptors, which are found mainly in the stomach; they are used for treating peptic ulcers and other types of acid-peptic diseases.
| hexylresorcinol, hexyl nicotinate, hexetidine | |
| histrelin acetate, homatropine hydrobromide, hormone replacement therapy |
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An endogenous substance responsible for some allergic responses in the eyes, nose, and skin (e.g. during a bout of hay fever). It is formed in the body from histidine. Histamine is released by mast cells in most tissues during inflammation. It is also secreted by some areas of the hypothalamus and functions as a metabotropic neurotransmitter belonging to the biogenic amines. It acts as a powerful vasodilator and increases the permeability of blood vessels.
Columbia Encyclopedia:
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histamine
histamine (hĭs'təmēn'), organic compound derived in the body from the amino acid histidine by the removal of a carboxyl group (COOH). Although found in many plant and animal tissues, histamine is specifically important in human physiology because it is one of the chemicals released from certain cells (particularly mast cells) upon tissue injury or during the neutralization of foreign material (antigens) by certain types of antibodies. Released histamine tends to dilate blood capillaries, often causing the skin to appear red and feel warm, and makes the capillaries more permeable, allowing fluid to escape into the tissues. This causes edema (swelling), usually manifested as acute urticaria (rapidly appearing hives, accompanied by severe itching). This sort of reaction is common to many allergies, such as food allergies, and the symptoms can often be controlled well with antihistamines. Unfortunately, histamine is not the only substance released under these conditions, and some allergies, particularly chronic ones such as asthma, are relatively resistant to antihistamine therapy.
Wiley Dictionary of Flavors:
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Histamine
A protein responsible for allergic reactions. It is developed in the body by the decarboxylation of the amino acid histidine through L-histidine decarboxidase. It is one of the chemicals in the complex series of events called anaphalactic shock. It is also released as part of sexual orgasm and is responsible for the sex flush among women. Antihistamines are used to counteract the ill effects of histamine in the body. See Food Allergy, Anaphylaxis, Food Intolerance.
Oxford Dictionary of Biochemistry:
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histamine
2-(4-imidazolyl)ethylamine, formed by the decarboxylation of l-histidine and present in many mammalian tissues, including the brain and spinal cord, with especially high concentrations in lung, skin, and intestine; it is stored in the granules of tissue mast cells and circulating basophil cells. Histamine is a potent vasodilator, increases capillary permeability, causes contraction of smooth muscle, regulates gastric secretion, and mediates allergic and anaphylactic conditions.
| hist+, hirustasin, hirulog | |
| histamine receptor, histamine-releasing factor, histatin |
Saunders Veterinary Dictionary:
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histamine
An amine, C5H9N3, produced by decarboxylation of histidine, found in all body tissues.
It induces capillary dilatation, which increases capillary permeability and lowers blood pressure; contraction of most smooth muscle tissue; increased gastric acid secretion; and acceleration of the heart rate. It is also a mediator of immediate hypersensitivity. There are two types of cellular receptors of histamine: H1-receptors, which mediate contraction of smooth muscle and capillary dilatation; and H2-receptors, which mediate acceleration of heart rate and promotion of gastric acid secretion. Both H1- and H2-receptors mediate the contraction of vascular smooth muscle. Histamine may also be a neurotransmitter in the central nervous system. It is used as a diagnostic aid in testing gastric secretion and in the diagnosis of pheochromocytoma.
There are two types of histamine antagonists that act at either the H1- or the H2-receptors. Drugs such as diphenhydramine and chlorpheniramine are referred to as antihistamines or H1-blockers; they block the effects of histamine on vascular, bronchial and gastrointestinal smooth muscle and on capillary permeability. They are used for relief of allergic and gastrointestinal disorders. Drugs such as cimetidine (Tagamet) are referred to as H2-blockers; they block the stimulation of gastric acid secretion and are used to treat gastrointestinal ulceration.
- h.-containing foods — some food sources, particularly some species of fish, have high levels of histamine; increased levels can also occur from improper storage which permits conversion of histidine to histamine, and an excessive carbohydrate content may promote bacterial growth, fermentation and production of histamine.
- h.-releasing foods — some foods can cause release of histamine from mast cells; these include egg white, shellfish and fish.
- h. shock — manipulation and particularly surgical trauma to large mast cell tumors may lead to decreased blood pressure and persistant bleeding caused by the release of histamine and vasoactive amines.
Mosby's Dental Dictionary:
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histamine
n
A compound found in all cells that is produced by the breakdown of histidine. Histamine is released in allergic, inflammatory reactions and causes dilation of capillaries, decreased blood pressure, increased secretion of gastric juice, and constriction of smooth muscles of the bronchi and uterus.
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categories related to 'histamine'
- Physiology - histamine: amine derived from amino acid histidine that is released in allergic reaction, causing dilation of blood vessels and lowering of blood pressure
Wikipedia on Answers.com:
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Histamine
For the use as an immunostimulant drug, see Histamine dihydrochloride.
| Histamine | |
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2-(1H-imidazol-4-yl)ethanamine |
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| Identifiers | |
| CAS number | 51-45-6  |
| PubChem | 774 |
| ChemSpider | 753 |
| UNII | 820484N8I3 |
| KEGG | D08040 |
| MeSH | Histamine |
| ChEBI | CHEBI:18295 |
| ChEMBL | CHEMBL90 |
| IUPHAR ligand | 1204 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H9N3 |
| Molar mass | 111.15 g mol−1 |
| Melting point |
83.5 °C (182.3 °F) |
| Boiling point |
209.5 °C (409.1 °F) |
| Solubility in water | Easily soluble in cold water, hot water[1] |
| Solubility | Easily soluble in methanol. Very slightly soluble in diethyl ether.[1] Easily soluble in ethanol. |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Histamine is an organic nitrogen compound involved in local immune responses as well as regulating physiological function in the gut and acting as a neurotransmitter.[2] Histamine triggers the inflammatory response. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. Histamine increases the permeability of the capillaries to white blood cells and some proteins, to allow them to engage pathogens in the infected tissues.[3]
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Contents
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Properties
Histamine forms colorless hygroscopic crystals that melt at 84°C, and are easily dissolved in water or ethanol, but not in ether. In aqueous solution histamine exists in two tautomeric forms, Nπ-H-histamine and Nτ-H-histamine.
Histamine has two basic centres, namely the aliphatic amino group and whichever nitrogen atom of the imidazole ring does not already have a proton. Under physiological conditions, the aliphatic amino group (having a pKa around 9.4) will be protonated, whereas the second nitrogen of the imidazole ring (pKa ≈ 5.8) will not be protonated.[4] Thus, histamine is normally protonated to a singly charged cation.
Synthesis and metabolism
Histamine is derived from the decarboxylation of the amino acid histidine, a reaction catalyzed by the enzyme L-histidine decarboxylase. It is a hydrophilic vasoactive amine.
Once formed, histamine is either stored or rapidly inactivated by its primary degradative enzymes, histamine-N-methyltransferase or diamine oxidase. In the central nervous system, histamine released into the synapses is primarily broken down by histamine-N-methyltransferase, while in other tissues both enzymes may play a role. Several other enzymes, including MAO-B and ALDH2, further process the immediate metabolites of histamine for excretion or recycling.
Bacteria also are capable of producing histamine using histidine decarboxylase enzymes unrelated to those found in animals. A non-infectious form of foodborne disease, scombroid poisoning, is due to histamine production by bacteria in spoiled food, particularly fish. Fermented foods and beverages naturally contain small quantities of histamine due to a similar conversion performed by fermenting bacteria or yeasts. Sake contains histamine in the 20–40 mg/L range; wines contain it in the 2–10 mg/L range.[5]
Storage and release
Most histamine in the body is generated in granules in mast cells or in white blood cells called basophils. Mast cells are especially numerous at sites of potential injury - the nose, mouth, and feet, internal body surfaces, and blood vessels. Non-mast cell histamine is found in several tissues, including the brain, where it functions as a neurotransmitter. Another important site of histamine storage and release is the enterochromaffin-like (ECL) cell of the stomach.
The most important pathophysiologic mechanism of mast cell and basophil histamine release is immunologic. These cells, if sensitized by IgE antibodies attached to their membranes, degranulate when exposed to the appropriate antigen. Certain amines and alkaloids, including such drugs as morphine, and curare alkaloids, can displace histamine in granules and cause its release. Antibiotics like polymyxin are also found to stimulate histamine release.
Histamine release occurs when allergens bind to mast-cell-bound IgE antibodies. Reduction of IgE overproduction may lower the likelihood of allergens finding sufficient free IgE to trigger a mast-cell-release of histamine.
Mechanism of action
Histamine exerts its actions by combining with specific cellular histamine receptors. The four histamine receptors that have been discovered in humans are designated H1 through H4, and are all G protein-coupled receptors (GPCR). Histamine receptors in insects, like Drosophila melanogaster, are histamine-gated chloride channels that function in inhibition of neurons.[6] Histamine-gated chloride channels are implicated in neurotransmission of peripheral sensory information in insects, especially in photoreception/vision. Two receptors subtypes have been identified in Drosophila, HClA and HClB.[7] There are no known GPCRs for histamine in insects.
| Type | Location | Function |
| H1 histamine receptor | Found on smooth muscle, endothelium, and central nervous system tissue | Causes, bronchoconstriction, bronchial smooth muscle contraction, vasodilation, separation of endothelial cells (responsible for hives), and pain and itching due to insect stings; the primary receptors involved in allergic rhinitis symptoms and motion sickness; sleep regulation. |
| H2 histamine receptor | Located on parietal cells and vascular smooth muscle cells | Primarily involved in vasodilation. Also stimulate gastric acid secretion |
| H3 histamine receptor | Found on central nervous system and to a lesser extent peripheral nervous system tissue | Decreased neurotransmitter release: histamine, acetylcholine, norepinephrine, serotonin |
| H4 histamine receptor | Found primarily in the basophils and in the bone marrow. It is also found on thymus, small intestine, spleen, and colon. | Plays a role in chemotaxis. |
Effects on nasal mucous membrane
Increased vascular permeability causes fluid to escape from capillaries into the tissues, which leads to the classic symptoms of an allergic reaction: a runny nose and watery eyes. Allergens can bind to IgE-loaded mast cells in the nasal cavity's mucous membranes. This can lead to three clinical responses:[8]
- sneezing due to histamine-associated sensory neural stimulation;
- hyper-secretion from glandular tissue; and
- nasal congestion due to vascular engorgement associated with vasodilation and increased capillary permeability.
Roles in the body
Sleep regulation
Histamine is released as a neurotransmitter. The cell bodies of histaminergics, the neurons which release histamine, are found in the posterior hypothalamus, in various tuberomammillary nuclei. From here, these neurons project throughout the brain, to the cortex through the medial forebrain bundle. Histaminergic action is known to modulate sleep. Classically, antihistamines (H1 histamine receptor antagonists) produce sleep. Likewise, destruction of histamine releasing neurons, or inhibition of histamine synthesis leads to an inability to maintain vigilance. Finally, H3 receptor antagonists increase wakefulness.
It has been shown that histaminergic cells have the most wakefulness-related firing pattern of any neuronal type thus far recorded. They fire rapidly during waking, fire more slowly during periods of relaxation/tiredness and completely stop firing during REM and NREM (non-REM) sleep. Histaminergic cells can be recorded firing just before an animal shows signs of waking.
Suppressive effects
While histamine has stimulatory effects upon neurons, it also has suppressive ones that protect against the susceptibility to convulsion, drug sensitization, denervation supersensitivity, ischemic lesions and stress.[9] It has also been suggested that histamine controls the mechanisms by which memories and learning are forgotten.[10]
Erection and sexual function
Libido loss and erectile failure can occur following histamine (H2) antagonists such as cimetidine and ranitidine.[11] The injection of histamine into the corpus cavernosum in men with psychogenic impotence produces full or partial erections in 74% of them.[12] It has been suggested that H2 antagonists may cause sexual difficulties by reducing the uptake[clarification needed] of testosterone.[11]
Schizophrenia
Metabolites of histamine are increased in the cerebrospinal fluid of people with schizophrenia, while the efficiency of H(1) receptor binding sites is decreased. Many atypical antipsychotic medications have the effect of increasing histamine turnover[clarification needed].[13]
Disorders
As an integral part of the immune system, histamine may be involved in immune system disorders and allergies. Mastocytosis is a rare disease in which there is a proliferation of mast cells that produce excess histamine. [14]
History
The properties of histamine, then called β-iminazolylethylamine, were first described in 1910 by the British scientists Henry H. Dale and P.P. Laidlaw.[15]
"H substance" or "substance H" are occasionally used in medical literature for histamine or a hypothetical histamine-like diffusible substance released in allergic reactions of skin and in the responses of tissue to inflammation.[citation needed]
See also
References
- ^ a b http://www.sciencelab.com/msds.php?msdsId=9924264
- ^ Marieb, E. (2001). Human anatomy & physiology. San Francisco: Benjamin Cummings. pp. 414. ISBN 0-8053-4989-8.
- ^ Di Giuseppe, M., et al. (2003). Nelson Biology 12. Toronto: Thomson Canada Ltd.. p. 473. ISBN 0-17-625987-2.
- ^ Paiva, T. B.; Tominaga, M.; Paiva, A. C. M. (1970). "Ionization of histamine, N-acetylhistamine, and their iodinated derivatives". Journal of Medicinal Chemistry 13 (4): 689–692. doi:10.1021/jm00298a025. PMID 5452432.
- ^ http://astrobiology.berkeley.edu/PDFs_articles/WineAnalysisAnalChem.pdf
- ^ Hardie RC (June 1989). "A histamine-activated chloride channel involved in neurotransmission at a photoreceptor synapse". Nature 339 (6227): 704–6. doi:10.1038/339704a0. PMID 2472552.
- ^ Pantazis A, Segaran A, Liu CH, et al. (July 2008). "Distinct roles for two histamine receptors (hclA and hclB) at the Drosophila photoreceptor synapse". J. Neurosci. 28 (29): 7250–9. doi:10.1523/JNEUROSCI.1654-08.2008. PMID 18632929. http://www.jneurosci.org/cgi/pmidlookup?view=long&pmid=18632929.
- ^ Monroe EW, Daly AF, Shalhoub RF (February 1997). "Appraisal of the validity of histamine-induced wheal and flare to predict the clinical efficacy of antihistamines". J. Allergy Clin. Immunol. 99 (2): S798–806. PMID 9042073.
- ^ Yanai, K; Tashiro, M (2007). "The physiological and pathophysiological roles of neuronal histamine: an insight from human positron emission tomography studies.". Pharmacology & therapeutics 113 (1): 1–15. doi:10.1016/j.pharmthera.2006.06.008. PMID 16890992.
- ^ Alvarez, EO (2009). "The role of histamine on cognition.". Behavioural brain research 199 (2): 183–9. doi:10.1016/j.bbr.2008.12.010. PMID 19126417.
- ^ a b White, JM; Rumbold, GR (1988). "Behavioural effects of histamine and its antagonists: a review.". Psychopharmacology 95 (1): 1–14. PMID 3133686.
- ^ Cará, AM; Lopes-Martins, RA; Antunes, E; Nahoum, CR; De Nucci, G (1995). "The role of histamine in human penile erection.". British journal of urology 75 (2): 220–4. doi:10.1111/j.1464-410X.1995.tb07315.x. PMID 7850330.
- ^ Ito, C (2004). "The role of the central histaminergic system on schizophrenia". Drug news & perspectives 17 (6): 383–7. doi:10.1358/dnp.2004.17.6.829029. PMID 15334189.
- ^ Valent P, Horny HP, Escribano L, et al. (July 2001). "Diagnostic criteria and classification of mastocytosis: a consensus proposal". Leuk. Res. 25 (7): 603–25. PMID 11377686. http://linkinghub.elsevier.com/retrieve/pii/S0145-2126(01)00038-8.
- ^ Dale HH, Laidlaw PP (December 1910). "The physiological action of β-iminazolylethylamine". J. Physiol. (Lond.) 41 (5): 318–44. PMC 1512903. PMID 16993030. http://jp.physoc.org/content/41/5/318.full.pdf.
External links
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This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)
Translations:
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Histamine
Nederlands (Dutch)
histamine (medicijn)
Français (French)
n. - histamine
Deutsch (German)
n. - Histamin
Ελληνική (Greek)
n. - (βιολ.) ισταμίνη
Português (Portuguese)
n. - histamina (f) (Quím.)
Español (Spanish)
n. - histamina
Svenska (Swedish)
n. - histamin (hormon i kroppens vävnader som frigörs vid överkänslighetsreaktioner)
中文（简体）(Chinese (Simplified))
组织胺
中文（繁體）(Chinese (Traditional))
n. - 組織胺
العربيه (Arabic)
(الاسم) الهستامين, مركب يكون في الارغوت وفي كثير من الانسجه الحيوانيه
עברית (Hebrew)
n. - תרכובת המכווצת שרירים ומרחיבה כלי-דם שמשחררים תאים בגוף בעת פציעה, היסטמין
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