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Histamine

histamine intolerance, histamine
Histamine is an organic nitrogenous compound involved in local immune responses as well as regulating physiological function in the gut and acting as a neurotransmitter for uterus3 Histamine is involved in the inflammatory response and has a central role as a mediator of pruritus4 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 tissues5

Contents

  • 1 Properties
  • 2 Synthesis and metabolism
  • 3 Storage and release
  • 4 Mechanism of action
  • 5 Roles in the body
    • 51 Vasodilation and a fall in blood pressure
    • 52 Effects on nasal mucous membrane
    • 53 Sleep-wake regulation
    • 54 Gastric acid release
    • 55 Protective effects
    • 56 Erection and sexual function
    • 57 Schizophrenia
    • 58 Multiple sclerosis
  • 6 Disorders
  • 7 History
  • 8 See also
  • 9 References
  • 10 External links

Propertiesedit

Histamine base, obtained as a mineral oil mull, melts at 83–84 °C6 Hydrochloride7 and phosphorus8 salts form white hygroscopic crystals 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 The imidazole ring has two nitrogens The nitrogen farthest away from the side chain is the 'tele' nitrogen and is denoted by a lowercase tau sign The nitrogen closest to the side chain is the 'pros' nitrogen and is denoted by the pi sign The position of the nitrogen with the hydrogen on it determines how the tautomer is named If the nitrogen with the hydrogen is in the tele position, then histamine is in the tele-tautomer form The tele-tautomer is preferred in solution

Tautomers of 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 94 will be protonated, whereas the second nitrogen of the imidazole ring pKa ≈ 58 will not be protonated9 Thus, histamine is normally protonated to a singly charged cation

Synthesis and metabolismedit

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

Conversion of histidine to histamine by histidine decarboxylase

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 range10

Storage and releaseedit

Mast cells

Most histamine in the body is generated in granules in mast cells and in white blood cells leukocytes called basophils and eosinophils 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 actionedit

In humans, histamine exerts its effects primarily by binding to G protein-coupled histamine receptors, designated H1 through H411 As of 2015, histamine is believed to activate ligand-gated chloride channels in the brain and intestinal epithelium

Type Location Function Source
Histamine H1 receptor
  • CNS: Produced in the histaminergic tuberomammillary nucleus, projecting to the dorsal raphe, locus coeruleus, and additional structures
  • Periphery: Smooth muscle, endothelium, sensory nerves
  • CNS: Sleep-wake cycle promotes wakefulness, body temperature, nociception, endocrine homeostasis, regulates appetite, involved in cognition
  • Periphery: Causes bronchoconstriction, bronchial smooth muscle contraction, vasodilation, promotes hypernociception visceral hypersensitivity, involved in itch perception and urticaria
111213
Histamine H2 receptor
  • CNS: Dorsal striatum caudate nucleus and putamen, cerebral cortex external layers, hippocampal formation, dentate nucleus of the cerebellumnote: almost all known H2 receptor antagonists eg, ranitidine, famotidine
  • Periphery: Located on parietal cells, vascular smooth muscle cells, neutrophils, mast cells, as well as on cells in the heart and uterus
  • CNS: Not established note: most known H2 receptor ligands are unable to cross the blood–brain barrier in sufficient concentrations to allow for neuropsychological and behavioral testing
  • Periphery: Primarily involved in vasodilation and stimulation of gastric acid secretion Modulates gastrointestinal function
111214
Histamine H3 receptor Found on central nervous system and to a lesser extent peripheral nervous system tissue Autoreceptor and heteroreceptor functions: decreased neurotransmitter release of histamine, acetylcholine, norepinephrine, serotonin
Modulates nociception, gastric acid secretion, and food intake
11
Histamine H4 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 mast cell chemotaxis, itch perception, cytokine production and secretion, and visceral hypersensitivity Other functions inflammation, allergy, cognition, etc have not been fully characterized 11
Histamine-gated chloride channel Putatively: CNS hypothalamus, thalamus and intestinal epithelium Brain: Produces fast inhibitory postsynaptic potentials
Intestinal epithelium: chloride secretion associated with secretory diarrhea
1112

Roles in the bodyedit

Although histamine is small compared to other biological molecules containing only 17 atoms, it plays an important role in the body It is known to be involved in 23 different physiological functions Histamine is known to be involved in many physiological functions because of its chemical properties that allow it to be versatile in binding It is Coulombic able to carry a charge, conformational, and flexible This allows it to interact and bind more easily15

Vasodilation and a fall in blood pressureedit

When injected intravenously, histamine causes most blood vessels to dilate, and hence causes a fall in the blood pressure16 This is a key mechanism in anaphylaxis, and is thought to be caused when histamine releases nitric oxide, endothelium-derived hyperpolarizing factors and other compounds from the endothelial cells

Effects on nasal mucous membrane edit

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:17

  1. sneezing due to histamine-associated sensory neural stimulation
  2. hyper-secretion from glandular tissue
  3. nasal congestion due to vascular engorgement associated with vasodilation and increased capillary permeability

Sleep-wake regulationedit

Histamine is released as a neurotransmitter The cell bodies of histamine neurons are found in the posterior hypothalamus, in the tuberomammillary nuclei From here, these neurons project throughout the brain, including to the cortex, through the medial forebrain bundle Histamine neurons increase wakefulness and prevent sleep18 Classically, antihistamines H1 histamine receptor antagonists which cross the blood-brain barrier produce drowsiness Newer antihistamines are designed to not cross into the brain and thus are less likely to cause sedation, although individual reactions, concomitant medications and dosage may increase the sedative effect Similar to the effect of older antihistamines, destruction of histamine releasing neurons, or inhibition of histamine synthesis leads to an inability to maintain vigilance Finally, H3 receptor antagonists increase wakefulness

Histaminergic neurons have a wakefulness-related firing pattern They fire rapidly during waking, fire more slowly during periods of relaxation/tiredness and completely stop firing during REM and NREM non-REM sleep

Gastric acid releaseedit

Enterochromaffin-like cells, located within the gastric glands of the stomach, release histamine that stimulates nearby parietal cells by binding to the apical H2 receptor Stimulation of the parietal cell induces the uptake of carbon dioxide and water from the blood, which is then converted to carbonic acid by the enzyme carbonic anhydrase Inside the cytoplasm of the parietal cell, the carbonic acid readily dissociates into hydrogen and bicarbonate ions The bicarbonate ions diffuse back through the basilar membrane and into the bloodstream, while the hydrogen ions are pumped into the lumen of the stomach via a K+/H+ ATPase pump Histamine release is halted when the pH of the stomach starts to decrease Antagonist molecules, like ranitidine, block the H2 receptor and prevent histamine from binding, causing decreased hydrogen ion secretion

Protective effectsedit

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 stress19 It has also been suggested that histamine controls the mechanisms by which memories and learning are forgotten20

Erection and sexual functionedit

Libido loss and erectile failure can occur during treatment with histamine H2 receptor antagonists such as cimetidine, ranitidine, and risperidone21 The injection of histamine into the corpus cavernosum in men with psychogenic impotence produces full or partial erections in 74% of them22 It has been suggested that H2 antagonists may cause sexual difficulties by reducing the uptakeclarification needed of testosterone21

Schizophreniaedit

Metabolites of histamine are increased in the cerebrospinal fluid of people with schizophrenia, while the efficiency of H1 receptor binding sites is decreased Many atypical antipsychotic medications have the effect of decreasing histamine production antagonist, because its use seems to be imbalanced in people with that disorder23

Multiple sclerosisedit

Histamine therapy for treatment of multiple sclerosis is currently being studied The different H receptors have been known to have different effects on the treatment of this disease The H1 and H4 receptors, in one study, have been shown to be counterproductive in the treatment of MS The H1 and H4 receptors are thought to increase permeability in the blood-brain barrier, thus increasing infiltration of unwanted cells in the central nervous system This can cause inflammation, and MS symptom worsening The H2 and H3 receptors are thought to be helpful when treating MS patients Histamine has been shown to help with T-cell differentiation This is important because in MS, the body's immune system attacks its own myelin sheaths on nerve cells which causes loss of signaling function and eventual nerve degeneration By helping T cells to differentiate, the T cells will be less likely to attack the body's own cells, and instead attack invaders24

Disordersedit

As an integral part of the immune system, histamine may be involved in immune system disorders25 and allergies Mastocytosis is a rare disease in which there is a proliferation of mast cells that produce excess histamine26

Historyedit

The properties of histamine, then called β-iminazolylethylamine, were first described in 1910 by the British scientists Henry H Dale and PP Laidlaw27 By 1913 the name histamine was in use, using combining forms of histo- + amine, yielding "tissue amine"

"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 inflammationcitation needed

See alsoedit

  • Scombroid food poisoning
  • Histamine antagonist antihistamine
  • Hay fever allergic rhinitis

Referencesedit

  1. ^ a b http://wwwsciencelabcom/msdsphpmsdsId=9924264
  2. ^ a b Vuckovic, Dajana; Pawliszyn, Janusz 15 March 2011 "Systematic Evaluation of Solid-Phase Microextraction Coatings for Untargeted Metabolomic Profiling of Biological Fluids by Liquid Chromatography−Mass Spectrometry" Analytical Chemistry Supporting Information 83 6: 1944–1954 doi:101021/ac102614v PMID 21332182 
  3. ^ Marieb, E 2001 Human anatomy & physiology San Francisco: Benjamin Cummings p 414 ISBN 0-8053-4989-8 
  4. ^ Andersen HH, Elberling J, Arendt-Nielsen L 2015 "Human surrogate models of histaminergic and non-histaminergic itch" Acta Dermato-Venereologica 95: 771–7 doi:102340/00015555-2146 PMID 26015312 
  5. ^ Di Giuseppe, M; et al 2003 Nelson Biology 12 Toronto: Thomson Canada p 473 ISBN 0-17-625987-2 
  6. ^ http://webbooknistgov/cgi/cbookcgiID=C51456&Mask=80
  7. ^ http://wwwsigmaaldrichcom/catalog/product/sigma/h7250lang=en&region=US
  8. ^ http://libnjutcmeducn/yaodian/ep/EP501E/16_monographs/17_monographs_d-k/histamine_phosphate/0144epdf
  9. ^ 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:101021/jm00298a025 PMID 5452432 
  10. ^ http://astrobiologyberkeleyedu/PDFs_articles/WineAnalysisAnalChempdf
  11. ^ a b c d e f Panula P, Chazot PL, Cowart M, et al 2015 "International Union of Basic and Clinical Pharmacology XCVIII Histamine Receptors" Pharmacol Rev 67 3: 601–55 doi:101124/pr114010249 PMC 4485016  PMID 26084539 
  12. ^ a b c Wouters MM, Vicario M, Santos J 2015 "The role of mast cells in functional GI disorders" Gut 65: 155–168 doi:101136/gutjnl-2015-309151 PMID 26194403 
  13. ^ Blandina, Patrizio; Munari, Leonardo; Provensi, Gustavo; Passani, Maria B 2012 "Histamine neurons in the tuberomamillary nucleus: a whole center or distinct subpopulations" Frontiers in Systems Neuroscience 6 doi:103389/fnsys201200033 
  14. ^ Maguire JJ, Davenport AP 29 November 2016 "H2 receptor" IUPHAR/BPS Guide to PHARMACOLOGY International Union of Basic and Clinical Pharmacology Retrieved 20 March 2017 
  15. ^ Noszal, B; Kraszni, M; Racz, A 2004 "Histamine: fundamentals of biological chemistry" In Falus, A; Grosman, N; Darvas, Z Histamine: Biology and Medical Aspects Budapest: SpringMed pp 15–28 ISBN 380557715X 
  16. ^ Dale, HH; Laidlaw, PP 31 December 1910 "The physiological action of beta-iminazolylethylamine" The Journal of Physiology 41 5: 318–44 doi:101113/jphysiol1910sp001406 PMC 1512903  PMID 16993030 
  17. ^ Monroe EW, Daly AF, Shalhoub RF February 1997 "Appraisal of the validity of histamine-induced wheal andï flare to predict the clinical efficacy of antihistamines" J Allergy Clin Immunol 99 2: S798–806 doi:101016/s0091-67499770128-3 PMID 9042073 
  18. ^ Brown, RE; Stevens, DR; Haas, HL 2001 "The Physiology of Brain Histamine" Progress in Neurobiology 63 6: 637–672 doi:101016/s0301-00820000039-3 PMID 11164999 
  19. ^ 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:101016/jpharmthera200606008 PMID 16890992 
  20. ^ Alvarez, EO 2009 "The role of histamine on cognition" Behavioural Brain Research 199 2: 183–9 doi:101016/jbbr200812010 PMID 19126417 
  21. ^ a b White, JM; Rumbold, GR 1988 "Behavioural effects of histamine and its antagonists: a review" Psychopharmacology 95 1: 1–14 doi:101007/bf00212757 PMID 3133686 
  22. ^ 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:101111/j1464-410X1995tb07315x PMID 7850330 
  23. ^ Ito, C 2004 "The role of the central histaminergic system on schizophrenia" Drug News & Perspectives 17 6: 383–7 doi:101358/dnp2004176829029 PMID 15334189 
  24. ^ Jadidi-Niaragh F, Mirshafiey A September 2010 "Histamine and histamine receptors in pathogenesis and treatment of multiple sclerosis" Neuropharmacology 59 3: 180–9 doi:101016/jneuropharm201005005 PMID 20493888 
  25. ^ E Zampeli; E Tiligada "The role of histamine H4 receptor in immune and inflammatory disorders" Department of Pharmacology, Medical School, National and Kapodistrian University of Athens, Athens, Greece 157: 24–33 doi:101111/j1476-5381200900151x PMC 2697784  PMID 19309354 
  26. ^ 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 doi:101016/S0145-21260100038-8 PMID 11377686 
  27. ^ Dale HH, Laidlaw PP December 1910 "The physiological action of β-iminazolylethylamine" PDF J Physiol Lond 41 5: 318–44 doi:101113/jphysiol1910sp001406 PMC 1512903  PMID 16993030 

External linksedit

  • Histamine MS Spectrum
  • DrugBank EXPT01785
  • Histamine bound to proteins in the PDB

histamine, histamine allergy, histamine blockers, histamine diet, histamine dihydrochloride, histamine foods, histamine intolerance, histamine intolerance food list, histamine reaction, histamine receptors


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Histamine


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