1147:, where deficiencies have been shown to lead to aggressive behavior and abnormal sleep-wake cycles in mice. Since brain histamine as a neurotransmitter regulates a number of neurophysiological functions, emphasis has been placed on the development of drugs to target histamine regulation. Yoshikawa et al. explores how the C314T, A939G, G179A, and T632C polymorphisms all impact HNMT enzymatic activity and the pathogenesis of various neurological disorders. These mutations can have either a positive or negative impact. Some patients with
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916:
3985:"Guideline on management of suspected adverse reactions to ingested histamine: Guideline of the German Society for Allergology and Clinical Immunology (DGAKI), the Society for Pediatric Allergology and Environmental Medicine (GPA), the Medical Association of German Allergologists (AeDA) as well as the Swiss Society for Allergology and Immunology (SGAI) and the Austrian Society for Allergology and Immunology (ĂGAI)"
803:
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substances are potent vasodilators, and have been demonstrated to mutually stimulate each other's release within the trigeminovascular system, a mechanism that could potentially instigate the onset of migraines. In patients with a deficiency in histamine degradation due to variants in the AOC1 gene that encodes
2101:
The urine test involves collecting all urine produced in a 24-hour period, which is then analyzed for the presence of 1,4-methyl-imidazolacetic acid. This comprehensive approach ensures a more accurate reflection of histamine metabolism over an extended period; as such, the 1,4-methyl-imidazolacetic
2073:
enzyme, a diet high in histamine has been observed to trigger migraines, that suggests a potential functional relationship between exogenous histamine and CGRP, which could be instrumental in understanding the genesis of diet-induced migraines, so that the role of histamine, particularly in relation
2089:
As a solution for the rapid metabolism of histamine, the measurement of histamine and its metabolites, particularly the 1,4-methyl-imidazolacetic acid, in a 24-hour urine sample, provides an efficient alternative to histamine measurement because the values of these metabolites remain elevated for a
2064:
is a presumed set of adverse reactions (such as flush, itching, rhinitis, etc.) to ingested histamine in food. The mainstream theory accepts that there may exist adverse reactions to ingested histamine, but does not recognize histamine intolerance as a separate condition that can be diagnosed.
1862:
receptors. This triggers carbon dioxide and water uptake from the blood, converted to carbonic acid by carbonic anhydrase. The acid dissociates into hydrogen and bicarbonate ions within the parietal cell. Bicarbonate returns to the bloodstream, while hydrogen is pumped into the stomach lumen.
1652:
It has been known for more than one hundred years that an intravenous injection of histamine causes a fall in the blood pressure. The underlying mechanism concerns both vascular hyperpermeability and vasodilation. Histamine binding to endothelial cells causes them to contract, thus increasing
1643:
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
2068:
The role of histamine in health and disease is an area of ongoing research. For example, histamine is researched in its potential link with migraine episodes, when there is a noted elevation in the plasma concentrations of both histamine and calcitonin gene-related peptide (CGRP). These two
790:
forms, identified by which of the two nitrogen atoms is protonated. The nitrogen farther away from the side chain is the 'tele' nitrogen and is denoted by a lowercase tau sign and the nitrogen closer to the side chain is the 'pros' nitrogen and is denoted by the pi sign. The tele tautomer,
1155:
placebo-controlled crossover trial, children with ADHD who responded with aggravated symptoms after consuming a challenge beverage were more likely to have HNMT polymorphisms at T939C and Thr105Ile. Histamine's role in neuroinflammation and cognition has made it a target of study for many
2035:
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
1190:. In such cases, the body may not be able to produce sufficient degradative enzymes to properly eliminate the excess histamine. Since MCAS is symptomatically characterized as such a broad disorder, it is difficult to diagnose and can be mislabeled as a variety of diseases, including
2097:
for 1,4-methyl-imidazolacetic acid, the metabolite of histamine. This test is a valuable tool in assessing the metabolism of histamine in the body, as direct measurement of histamine in the serum has low diagnostic value due to the specificities of histamine metabolism.
1135:
increased the risk for reduced DAO activity. People with genotypes for reduced DAO activity can avoid foods high in histamine, such as alcohol, fermented foods, and aged foods, to attenuate any allergic reactions. Additionally, they should be aware whether any
2102:
acid urine test offered by commercial labs is currently the most reliable method to determine the rate of histamine metabolism, which may be helpful for the health care practitioners to assess individualâs health status, such as to diagnose
1768:, other hypothalamic nuclei, medial septum, the nucleus of the diagonal band, ventral tegmental area, amygdala, striatum, substantia nigra, hippocampus, thalamus and elsewhere. The histamine neurons in the TMN are involved in regulating the
1209:, airway obstruction, and production of excess mucus. Mutations in histamine degradation are more common in patients with a combination of asthma and allergen hypersensitivity than in those with just asthma. The HNMT-464 TT and HNMT-1639 TT
1183:, and cannot be properly degraded. The abnormal release of histamine can be caused by either dysfunctional internal signals from defective mast cells or by the development of clonal mast cell populations through mutations occurring in the
2991:
Stevenson J, Sonuga-Barke E, McCann D, Grimshaw K, Parker KM, Rose-Zerilli MJ, et al. (September 2010). "The role of histamine degradation gene polymorphisms in moderating the effects of food additives on children's ADHD symptoms".
2074:
to CGRP, is a promising area of research for elucidating the mechanisms underlying migraine development and aggravation, especially relevant in the context of dietary triggers and genetic predispositions related to histamine metabolism.
973:, 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.
2795:
GriauzdaitÄ K, Maselis K, ĆœvirblienÄ A, Vaitkus A, JanÄiauskas D, BanaitytÄ-BaleiĆĄienÄ I, et al. (September 2020). "Associations between migraine, celiac disease, non-celiac gluten sensitivity and activity of diamine oxidase".
2145:"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.
1074:
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.
1830:
do not readily permeate the bloodâbrain barrier and thus are less likely to cause sedation, although individual reactions, concomitant medications and dosage may increase the likelihood of a sedating effect. In contrast,
2026:
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
1126:
were positively correlated with having lower DAO serum levels. Low DAO activity can have more severe consequences as mutations in the ABP1 alleles of the AOC1 gene have been associated with ulcerative colitis.
1005:. Mast cells are especially numerous at sites of potential injury â the nose, mouth, and feet, internal body surfaces, and blood vessels. Non-mast cell histamine is found in several tissues, including the
2234:
Vuckovic D, Pawliszyn J (March 2011). "Systematic evaluation of solid-phase microextraction coatings for untargeted metabolomic profiling of biological fluids by liquid chromatography-mass spectrometry".
1673:
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
1583:, itch perception, cytokine production and secretion, and visceral hypersensitivity. Other putative functions (e.g., inflammation, allergy, cognition, etc.) have not been fully characterized.
1114:
of the small intestine mucosa. Reduced DAO activity is associated with gastrointestinal disorders and widespread food intolerances. This is due to an increase in histamine absorption through
1780:
with an individual's state of arousal. These neurons fire rapidly during periods of wakefulness, fire more slowly during periods of relaxation/tiredness, and stop firing altogether during
4531:
2521:
863:
is slightly basic (with a normal pH range of 7.35 to 7.45) therefore the predominant form of histamine present in human blood is monoprotic at the aliphatic nitrogen. Histamine is a
3983:
Reese I, Ballmer-Weber B, Beyer K, Dölle-Bierke S, Kleine-Tebbe J, Klimek L, LÀmmel S, Lepp U, Saloga J, SchÀfer C, Szepfalusi Z, Treudler R, Werfel T, Zuberbier T, Worm M (2021).
556:
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610:
1644:
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 easily.
3948:
Valent P, Horny HP, Escribano L, Longley BJ, Li CY, Schwartz LB, et al. (July 2001). "Diagnostic criteria and classification of mastocytosis: a consensus proposal".
3649:
Yanai K, Tashiro M (January 2007). "The physiological and pathophysiological roles of neuronal histamine: an insight from human positron emission tomography studies".
4046:"Is calcitonin gene-related peptide (CGRP) the missing link in food histamine-induced migraine? A review of functional gut-to-trigeminovascular system connections"
1171:. They act as an alarm to trigger inflammatory responses by the immune system. Their presence in the digestive system enables them to serve as an early barrier to
403:
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1658:
3407:
2602:
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can occur from the inhibition of histamine biosynthesis or the loss (i.e., degeneration or destruction) of histamine-releasing neurons in the TMN.
2036:
degeneration). By helping T cells to differentiate, the T cells will be less likely to attack the body's own cells, and instead, attack invaders.
7395:
6814:
6055:
4517:
4381:
1895:, ischemic lesions and stress. It has also been suggested that histamine controls the mechanisms by which memories and learning are forgotten.
6823:
4277:
3590:
3524:
1998:
medications have the effect of increasing histamine production, because histamine levels seem to be imbalanced in people with that disorder.
1724:
6206:
2542:
3856:
Jadidi-Niaragh F, Mirshafiey A (September 2010). "Histamine and histamine receptors in pathogenesis and treatment of multiple sclerosis".
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neurological disorders, including autism spectrum disorder (ASD). De novo deletions in the HNMT gene have also been associated with ASD.
5544:
4584:
2841:"Severity of ulcerative colitis is associated with a polymorphism at diamine oxidase gene but not at histamine N-methyltransferase gene"
1213:
are significantly more common among children with allergic asthma, the latter of which is overrepresented in
African-American children.
1151:
have been shown to exhibit exacerbated symptoms in response to food additives and preservatives, due in part to histamine release. In a
2010:
is currently being studied. The different H receptors have been known to have different effects on the treatment of this disease. The H
4227:
1201:
Histamine is often explored as a potential cause for diseases related to hyper-responsiveness of the immune system. In patients with
2454:
2287:
1622:
368:
6999:
6994:
3032:"Systemic mast cell activation disease: the role of molecular genetic alterations in pathogenesis, heritability and diagnostics"
1887:
While histamine has stimulatory effects upon neurons, it also has suppressive ones that protect against the susceptibility to
7315:
6081:
4330:
4165:
4114:
3783:
CarĂĄ AM, Lopes-Martins RA, Antunes E, Nahoum CR, De Nucci G (February 1995). "The role of histamine in human penile erection".
3441:
Noszal B, Kraszni M, Racz A (2004). "Histamine: fundamentals of biological chemistry". In Falus A, Grosman N, Darvas Z (eds.).
2217:
2082:
Histamine, a biogenic amine, involves many physiological functions, including the immune response, gastric acid secretion, and
4303:"New approach for the diagnosis of histamine intolerance based on the determination of histamine and methylhistamine in urine"
4087:"New approach for the diagnosis of histamine intolerance based on the determination of histamine and methylhistamine in urine"
3291:"Histamine modulation of urinary bladder urothelium, lamina propria and detrusor contractile activity via H1 and H2 receptors"
6505:
3450:
2536:
1092:
241:
2566:
Paiva TB, Tominaga M, Paiva AC (July 1970). "Ionization of histamine, N-acetylhistamine, and their iodinated derivatives".
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6175:
2413:
2344:
Keppel
Hesselink JM (December 2015). "The terms 'autacoid', 'hormone' and 'chalone' and how they have shifted with time".
2164:
1176:
1123:
1088:
935:
4189:"Development of a HILIC-MS/MS method for the quantification of histamine and its main metabolites in human urine samples"
617:
7329:
6525:
6500:
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2114:
The properties of histamine, then called ÎČ-imidazolylethylamine, were first described in 1910 by the
British scientists
1892:
1661:
and other compounds, resulting in blood vessel dilation. These two mechanisms play a key role in the pathophysiology of
1436:
311:
1978:
antagonists may cause sexual dysfunction by reducing the functional binding of testosterone to its androgen receptors.
1236:. As of 2015, histamine is believed to activate ligand-gated chloride channels in the brain and intestinal epithelium.
332:
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7004:
6861:
6807:
6074:
5325:
4495:
3542:"Appraisal of the validity of histamine-induced wheal and flare to predict the clinical efficacy of antihistamines"
2603:"Analysis of neuroactive amines in fermented beverages using a portable microchip capillary electrophoresis system"
1974:
in males with psychogenic impotence produces full or partial erections in 74% of them. It has been suggested that H
1855:
1246:
1222:
1014:
864:
523:
2892:"Association of single nucleotide polymorphisms in the diamine oxidase gene with diamine oxidase serum activities"
1653:
vascular leak. It also stimulates synthesis and release of various vascular smooth muscle cell relaxants, such as
1140:
they are taking contain any histamine-producing strains and consult with their doctor to receive proper support .
1103:(ASD). Histamine degradation is crucial to the prevention of allergic reactions to otherwise harmless substances.
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31:
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1191:
272:
4256:
BĂ€hre H, Kaever V (2017). "Analytical
Methods for the Quantification of Histamine and Histamine Metabolites".
1811:
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7390:
7101:
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3419:
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Nieto-Alamilla G, MĂĄrquez-GĂłmez R, GarcĂa-GĂĄlvez AM, Morales-Figueroa GE, Arias-Montaño JA (November 2016).
1971:
1765:
1013:, where it functions as a neurotransmitter. Another important site of histamine storage and release is the
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218:
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2045:
1832:
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1083:
Histamine is released by mast cells as an immune response and is later degraded primarily by two enzymes:
954:-methyltransferase, while in other tissues both enzymes may play a role. Several other enzymes, including
760:
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Wright C, Shin JH, Rajpurohit A, Deep-Soboslay A, Collado-Torres L, Brandon NJ, et al. (May 2017).
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GarcĂa-Martin E, Mendoza JL, MartĂnez C, Taxonera C, Urcelay E, Ladero JM, et al. (January 2006).
2086:. However, its rapid metabolism makes it challenging to measure histamine levels directly in plasma.
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1951:
1290:
160:
120:
7365:
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4569:
3081:"Genetic Variation along the Histamine Pathway in Children with Allergic versus Nonallergic Asthma"
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1800:
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entering the body. People who suffer from widespread sensitivities and allergic reactions may have
970:
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349:
86:
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is a rare disease in which there is a proliferation of mast cells that produce excess histamine.
2007:
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or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see
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5492:
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5196:
5176:
5166:
5076:
3740:
White JM, Rumbold GR (1988). "Behavioural effects of histamine and its antagonists: a review".
505:
Easily soluble in methanol. Very slightly soluble in diethyl ether. Easily soluble in ethanol.
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6898:
6355:
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3240:"Histamine neurons in the tuberomamillary nucleus: a whole center or distinct subpopulations?"
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2018:
receptors, in one study, have been shown to be counterproductive in the treatment of MS. The H
1757:
1111:
716:
704:
5834:
5829:
1024:
The most important pathophysiologic mechanism of mast cell and basophil histamine release is
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1337:
1329:
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680:
649:
488:
426:
2702:
Thompson JS (1990). "Significance of the intestinal gradient of diamine oxidase activity".
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Comas-Basté O, Latorre-Moratalla M, Bernacchia R, Veciana-Nogués M, Vidal-Carou M (2017).
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Comas-Basté O, Latorre-Moratalla M, Bernacchia R, Veciana-Nogués M, Vidal-Carou M (2017).
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enzymes unrelated to those found in animals. A non-infectious form of foodborne disease,
943:
876:
855:â 5.8) will not be protonated. Thus, histamine is normally protonated to a singly charged
180:
4029: This article incorporates text from this source, which is available under the
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Please expand the section to include this information. Further details may exist on the
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receptor and prevent histamine from binding, causing decreased hydrogen ion secretion.
1527:
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353:
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Maintz L, Yu CF, RodrĂguez E, Baurecht H, Bieber T, Illig T, et al. (July 2011).
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3143:"International Union of Basic and Clinical Pharmacology. XCVIII. Histamine Receptors"
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1995:
1987:
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1304:
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1036:
1025:
962:, further process the immediate metabolites of histamine for excretion or recycling.
779:
637:
477:
467:
211:
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3635:
3141:
Panula P, Chazot PL, Cowart M, Gutzmer R, Leurs R, Liu WL, et al. (July 2015).
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in sufficient concentrations to allow for neuropsychological and behavioral testing)
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3005:
2054:
1745:
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1705:
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1511:
1478:
1359:
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1118:, which increases histamine concentration in the bloodstream. One study found that
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572:
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562:
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2439:
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4045:
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3606:
Brown RE, Stevens DR, Haas HL (April 2001). "The physiology of brain histamine".
3583:
Basic
Neurochemistry - Principles of Molecular, Cellular and Medical Neurobiology
1986:
Metabolites of histamine are increased in the cerebrospinal fluid of people with
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3351:"Histamine mediated autocrine signalling in mesenteric perilymphatic mast cells"
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4102:
3818:
Ito C (2004). "The role of the central histaminergic system on schizophrenia".
3366:
3314:
3215:
3198:
2809:
2132:
7124:
7026:
7016:
6955:
6950:
6612:
6560:
6520:
6401:
6396:
6378:
6324:
6105:
6020:
5909:
5874:
5854:
5849:
5793:
5698:
5693:
5688:
5668:
5658:
5638:
5623:
5613:
5603:
5588:
5583:
5383:
5311:
5282:
5274:
5201:
5136:
5096:
5091:
5056:
5051:
5011:
5006:
4931:
4856:
4781:
4746:
4736:
4706:
4686:
4666:
4626:
3697:
1963:
1959:
1888:
1872:
1868:
1815:
1712:
1580:
1444:
1423:
1312:
1187:
1115:
1107:
1064:
998:
930:
Once formed, histamine is either stored or rapidly inactivated by its primary
906:
880:
845:
748:
736:
641:
499:
454:
231:
171:
4302:
4086:
3256:
3096:
2655:"Altered expression of histamine signaling genes in autism spectrum disorder"
1744:. The cell bodies of these neurons are located in a portion of the posterior
7134:
7119:
7031:
6886:
6629:
6339:
6252:
6005:
5914:
5864:
5643:
5524:
5387:
5375:
5341:
5329:
5315:
5266:
5254:
5216:
5206:
5156:
5111:
5061:
5036:
4951:
4926:
4901:
4891:
4881:
4846:
4786:
4726:
4661:
4651:
4631:
2049:
1844:
1709:
1698:
1679:
1531:
1481:
secretion. Urinary bladder relaxation. Modulates gastrointestinal function.
1371:
1180:
1159:
Mast cells serve an important immunological role by defending the body from
1137:
1095:(SNPs) at these genes are associated with a wide variety of disorders, from
1068:
1002:
920:
883:
823:
732:
728:
700:
692:
673:
536:
4479:
4326:
4287:
4212:
4110:
4071:
4018:
3969:
3934:
3877:
3839:
3715:
3670:
3627:
3501:
3384:
3332:
3275:
3224:
3176:
3114:
3065:
3013:
2977:
2958:
2918:
2876:
2857:
2817:
2781:
2688:
2629:
2409:
2365:
2330:
2321:
2304:
2256:
1908:
4430:
4377:
4161:
3804:
3761:
3567:
3158:
2723:
2587:
2400:
1839:
increase wakefulness. Similar to the sedative effect of first-generation H
1131:
recessive genotypes at the rs2052129, rs2268999, rs10156191 and rs1049742
6866:
6550:
6414:
6319:
6130:
6025:
5984:
5924:
5819:
5814:
5798:
5534:
5529:
5425:
5333:
5294:
5081:
4636:
3349:
Pal S, Gasheva OY, Zawieja DC, Meininger CM, Gashev AA J (January 2020).
2762:
1553:
1341:
1282:
1205:, abnormal histamine receptor activation in the lungs is associated with
1172:
1128:
1119:
1056:
1052:
1032:
887:
831:
827:
787:
724:
696:
669:
633:
191:
4406:"Increased Urine Histamine and Methylhistamine in Interstitial Cystitis"
4269:
4187:
Nelis M, Decraecker L, Boeckxstaens G, Augustijns P, Cabooter D (2020).
3901:"The role of histamine H4 receptor in immune and inflammatory disorders"
3418:. International Union of Basic and Clinical Pharmacology. Archived from
2579:
763:, melts at 83â84 °C. Hydrochloride and phosphorus salts form white
200:
6843:
6750:
6666:
6262:
6247:
6237:
6227:
6180:
6150:
5824:
5775:
5562:
5379:
4597:
3753:
3706:
2670:
2044:
As an integral part of the immune system, histamine may be involved in
1407:
1160:
1044:
1018:
947:
795:-histamine, is preferred in solution as compared to the pros tautomer,
775:
767:
720:
688:
679:; however, in recent years, histamine has been recognized as a central
665:
287:
4000:
3344:
3342:
2942:"Role of Histamine in Modulating the Immune Response and Inflammation"
2715:
2648:
2646:
2621:
2357:
2248:
834:. Under physiological conditions, the aliphatic amino group (having a
44:
6257:
6185:
5979:
5770:
1738:
1734:
1569:
1561:
1452:
1202:
1132:
1063:
alkaloids, can displace histamine in granules and cause its release.
1060:
891:
856:
661:
151:
6066:
2381:"Human surrogate models of histaminergic and non-histaminergic itch"
587:
Except where otherwise noted, data are given for materials in their
1618:
Putatively: CNS (hypothalamus, thalamus) and intestinal epithelium
261:
7311:
7299:
References for all endogenous human TAAR1 ligands are provided at
7225:
7188:
7174:
6834:
6479:
6285:
2735:
2733:
2601:
Jayarajah CN, Skelley AM, Fortner AD, Mathies RA (November 2007).
2305:"The Histamine H3 Receptor: Structure, Pharmacology, and Function"
2138:
1858:
in the stomach release histamine, stimulating parietal cells via H
1761:
1534:. Modulates nociception, gastric acid secretion, and food intake.
1448:
1179:(MCAS), in which excessive amounts of histamine are released from
1048:
1010:
988:
959:
955:
914:
909:
860:
801:
676:
653:
131:
119:
109:
7056:
4354:"Stimulated Release of Urine Histamine in Interstitial Cystitis"
4352:
Yun SK, Laub DJ, Weese DL, Lad PM, Leach GE, Zimmern PE (1992).
4138:"Gas chromatographic analysis of histamine metabolites in urine"
3844:
Many atypical antipsychotics also increased histamine turnovers.
1804:
1785:
1367:
1221:
In humans, histamine exerts its effects primarily by binding to
978:
974:
810:-histamine), on the left is more stable than the pros tautomer (
252:
6796:
6070:
4513:
1694:
sneezing due to histamine-associated sensory neural stimulation
1902:
1822:
receptors in the tuberomammillary nucleus. The newer class of
1675:
1029:
3684:
Alvarez EO (May 2009). "The role of histamine on cognition".
2940:
Branco AC, Yoshikawa FS, Pietrobon AJ, Sato MN (2018-08-27).
2379:
Andersen HH, Elberling J, Arendt-Nielsen L (September 2015).
1704:
nasal congestion due to vascular engorgement associated with
946:. In the central nervous system, histamine released into the
664:. Discovered in 1910, histamine has been considered a local
337:
1626:
Intestinal epithelium: chloride secretion (associated with
672:) because it's produced without involvement of the classic
3085:
American
Journal of Respiratory Cell and Molecular Biology
1756:, which projects widely throughout the brain and includes
1752:(TMN). The histamine neurons in this region comprise the
7310:
References for synthetic TAAR1 agonists can be found at
4403:
El-Mansoury M, Boucher W, Sant G, Theoharides T (1994).
3079:
Anvari S, Vyhlidal CA, Dai H, Jones BL (December 2015).
1477:: Primarily involved in vasodilation and stimulation of
377:
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
4446:"The physiological action of beta-iminazolylethylamine"
3468:"The physiological action of beta-iminazolylethylamine"
997:
Most histamine in the body is generated in granules in
965:
Bacteria also are capable of producing histamine using
605:
387:
InChI=1/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
3136:
3134:
3132:
3130:
3128:
3126:
3124:
3030:
Haenisch B, Nöthen MM, Molderings GJ (November 2012).
848:, whereas the second nitrogen of the imidazole ring (p
3289:
Stromberga Z, Chess-Williams R, Moro C (March 2019).
3238:
Blandina P, Munari L, Provensi G, Passani MB (2012).
7275:
7261:
7233:
7224:
7206:
7196:
7187:
7165:
7147:
6982:
6851:
6842:
6833:
6738:
6704:
6684:
6677:
6665:
6628:
6621:
6611:
6579:
6488:
6478:
6446:
6426:
6348:
6307:
6298:
6271:
6220:
6194:
6123:
6114:
6104:
5993:
5949:
5937:
5807:
5748:
5736:
5571:
5517:
5505:
4606:
4562:
4550:
3199:"The role of mast cells in functional GI disorders"
1994:receptor binding sites is decreased. Many atypical
830:atom of the imidazole ring does not already have a
240:
4404:
2740:Yoshikawa T, Nakamura T, Yanai K (February 2019).
2271:
1863:Histamine release ceases as stomach pH decreases.
1240:Biological targets of histamine in the human body
4307:Journal of Pharmaceutical and Biomedical Analysis
4091:Journal of Pharmaceutical and Biomedical Analysis
3540:Monroe EW, Daly AF, Shalhoub RF (February 1997).
3192:
3190:
3188:
3186:
977:contains histamine in the 20â40 mg/L range;
3197:Wouters MM, Vicario M, Santos J (January 2016).
2216:(Technical report). sciencelab.com. 2013-05-21.
2206:
2204:
1091:(HNMT), coded by the HNMT gene. The presence of
786:, the imidazole ring of histamine exists in two
299:
1071:are also found to stimulate histamine release.
95:
3546:The Journal of Allergy and Clinical Immunology
2090:much longer period than the histamine itself.
6808:
6082:
4525:
3406:Maguire JJ, Davenport AP (29 November 2016).
2278:. San Francisco: Benjamin Cummings. pp.
1690:. This can lead to three clinical responses:
1001:and in white blood cells (leukocytes) called
27:Organic compound involved in immune responses
8:
1776:of histamine neurons in the TMN is strongly
482:209.5 °C (409.1 °F; 482.6 K)
30:For the use as an immunostimulant drug, see
2750:International Journal of Molecular Sciences
1954:can occur during treatment with histamine H
1659:endothelium-derived hyperpolarizing factors
1358:contraction, urinary bladder contractions,
1285:of the output neurons of the histaminergic
691:. As part of an immune response to foreign
472:83.5 °C (182.3 °F; 356.6 K)
7230:
7193:
6848:
6839:
6815:
6801:
6793:
6735:
6701:
6681:
6672:
6625:
6618:
6585:
6485:
6452:
6304:
6120:
6111:
6089:
6075:
6067:
5946:
5745:
5514:
4559:
4532:
4518:
4510:
4228:"2-(1-methyl-1H-imidazol-4-yl)acetic acid"
2229:
2227:
759:Histamine base, obtained as a mineral oil
352:
221:
179:
36:
4469:
4061:
4008:
3924:
3705:
3557:
3491:
3374:
3322:
3265:
3255:
3214:
3166:
3104:
3055:
2967:
2957:
2866:
2856:
2771:
2761:
2678:
2399:
2320:
1843:antihistamines, an inability to maintain
1467:receptor ligands are unable to cross the
319:
3735:
3733:
1772:and promote arousal when activated. The
1238:
981:contain it in the 2â10 mg/L range.
687:and has a central role as a mediator of
494:Easily soluble in cold water, hot water
3585:. Waltham, USA: Elsevier. p. 337.
3445:. Budapest: SpringMed. pp. 15â28.
2200:
1648:Vasodilation and fall in blood pressure
408:
373:
348:
277:
199:
3443:Histamine: Biology and Medical Aspects
3355:Am J Physiol Regul Integr Comp Physiol
1970:. The injection of histamine into the
950:is primarily broken down by histamine-
212:
6824:Human trace amine-associated receptor
4444:Dale HH, Laidlaw PP (December 1910).
4258:Handbook of Experimental Pharmacology
3466:Dale HH, Laidlaw PP (December 1910).
3025:
3023:
2346:Autonomic & Autacoid Pharmacology
1725:Ascending reticular activating system
1463:: Not established (note: most known H
380:Key: NTYJJOPFIAHURM-UHFFFAOYSA-N
159:
139:
7:
2213:Histamine Material Safety Data Sheet
1733:that is released from histaminergic
576:
566:
4384:from the original on 18 August 2024
4333:from the original on 18 August 2024
4238:from the original on 18 August 2024
4168:from the original on 18 August 2024
4117:from the original on 18 August 2024
2445:. Toronto: Thomson Canada. p.
2006:Histamine therapy for treatment of
390:Key: NTYJJOPFIAHURM-UHFFFAOYAP
290:
260:
4797:Etybenzatropine (ethylbenztropine)
3899:Zampeli E, Tiligada E (May 2009).
3797:10.1111/j.1464-410X.1995.tb07315.x
2994:The American Journal of Psychiatry
2093:Commercial laboratories provide a
1623:inhibitory postsynaptic potentials
25:
7115:Ralmitaront (RG-7906, RO-6889450)
3517:Cellular and molecular immunology
3244:Frontiers in Systems Neuroscience
2845:World Journal of Gastroenterology
2500:"Histamine dihydrochloride H7250"
1669:Effects on nasal mucous membrane
1028:. These cells, if sensitized by
4044:De Mora F, Messlinger K (2024).
4024:
3917:10.1111/j.1476-5381.2009.00151.x
3870:10.1016/j.neuropharm.2010.05.005
3663:10.1016/j.pharmthera.2006.06.008
3416:IUPHAR/BPS Guide to Pharmacology
3048:10.1111/j.1365-2567.2012.03627.x
2911:10.1111/j.1398-9995.2011.02548.x
2746:-Methyltransferase in the Brain"
2510:from the original on 2015-08-09.
2437:Di Giuseppe M, Fraser D (2003).
2220:from the original on 2012-03-24.
1907:
1087:(DAO), coded by AOC1 genes, and
1043:when exposed to the appropriate
1015:enterochromaffin-like (ECL) cell
595:
444:
438:
52:
43:
6051:Monoamine metabolism modulators
3905:British Journal of Pharmacology
3651:Pharmacology & Therapeutics
2419:from the original on 2019-03-30
1093:single nucleotide polymorphisms
683:. Histamine is involved in the
591:(at 25 °C , 100 kPa).
6882:Norepinephrine (noradrenaline)
6335:Norepinephrine (noradrenaline)
4462:10.1113/jphysiol.1910.sp001406
3484:10.1113/jphysiol.1910.sp001406
3006:10.1176/appi.ajp.2010.09101529
2568:Journal of Medicinal Chemistry
2274:Human anatomy & physiology
1810:) are capable of crossing the
1560:. It is also expressed in the
1106:DAO is typically expressed in
875:Histamine is derived from the
638:immune responses communication
432:
1:
7396:Carbonic anhydrase activators
7330:Receptor/signaling modulators
6056:Monoamine reuptake inhibitors
6046:Receptor/signaling modulators
4423:10.1016/S0022-5347(17)32737-4
4370:10.1016/S0022-5347(17)36844-1
4205:10.1016/j.talanta.2020.121328
4154:10.1016/S0021-9673(01)98675-3
3962:10.1016/S0145-2126(01)00038-8
3620:10.1016/s0301-0082(00)00039-3
3559:10.1016/s0091-6749(97)70128-3
2180:Histamine receptor antagonist
2170:Hay fever (allergic rhinitis)
2165:Histamine N-methyltransferase
1958:receptor antagonists such as
1922:sexual dysfunction in females
1447:, as well as on cells in the
1362:, promotes hypernociception (
1177:mast cell activation syndrome
1089:histamine-N-methyltransferase
4063:10.1016/j.drudis.2024.103941
3832:10.1358/dnp.2004.17.6.829029
3820:Drug News & Perspectives
1899:Erection and sexual function
1893:denervation supersensitivity
1437:vascular smooth muscle cells
1297:, and additional structures.
770:and are easily dissolved in
6862:monoamine neurotransmitters
5679:Quisultazine (quisultidine)
5326:Tetracyclic antidepressants
4501:Histamine bound to proteins
4142:Journal of Chromatography A
2142:, yielding "tissue amine".
1990:, while the efficiency of H
1856:Enterochromaffin-like cells
1818:by antagonizing histamine H
731:tissues. It consists of an
707:. Histamine increases the
695:, histamine is produced by
636:compound involved in local
7412:
4642:Benzatropine (benztropine)
4319:10.1016/j.jpba.2017.06.029
4103:10.1016/j.jpba.2017.06.029
3785:British Journal of Urology
3686:Behavioural Brain Research
3367:10.1152/ajpregu.00255.2019
3315:10.1038/s41598-019-40384-1
3216:10.1136/gutjnl-2015-309151
2810:10.1016/j.mehy.2020.109738
2388:Acta Dermato-Venereologica
1722:
1579:Plays a role in mast cell
1247:G-protein coupled receptor
1129:Heterozygous or homozygous
1055:, including such drugs as
865:monoamine neurotransmitter
826:amino group and whichever
723:, to allow them to engage
29:
7295:
6588:
6455:
6141:Glutamic acid (glutamate)
6136:Aspartic acid (aspartate)
6038:
5356:Tricyclic antidepressants
5212:Sequifenadine (bicarphen)
4450:The Journal of Physiology
3698:10.1016/j.bbr.2008.12.010
3519:. Elsevier. p. 447.
3472:The Journal of Physiology
2946:Mediators of Inflammation
2095:24-hour urine sample test
1737:which project out of the
1589:
1506:peripheral nervous system
1364:visceral hypersensitivity
1143:HNMT is expressed in the
814:-histamine) on the right.
585:
549:
419:
399:
364:
79:
74:-Imidazol-4-yl)ethanamine
65:
60:
51:
42:
32:Histamine dihydrochloride
6877:Epinephrine (adrenaline)
6325:Epinephrine (adrenaline)
4994:Second/third-generation:
4827:Hydroxyethylpromethazine
4232:pubchem.ncbi.nlm.nih.gov
3608:Progress in Neurobiology
3257:10.3389/fnsys.2012.00033
3097:10.1165/rcmb.2014-0493OC
2659:Translational Psychiatry
2185:Scombroid food poisoning
1754:brain's histamine system
1750:tuberomammillary nucleus
1591:Ligand-gated ion channel
1328:(promotes wakefulness),
1289:, which projects to the
1287:tuberomammillary nucleus
1192:irritable bowel syndrome
1101:autism spectrum disorder
900:-histidine decarboxylase
871:Synthesis and metabolism
741:physiological conditions
640:, as well as regulating
7012:-Dimethylphenethylamine
5634:Lavoltidine (loxtidine)
5247:Atypical antipsychotics
5192:Quifenadine (phencarol)
4857:Mepyramine (pyrilamine)
4617:4-Methyldiphenhydramine
3147:Pharmacological Reviews
2046:immune system disorders
1766:medial forebrain bundle
1504:and to a lesser extent
1344:, involved in cognition
967:histidine decarboxylase
925:histidine decarboxylase
642:physiological functions
7135:Ulotaront (SEP-363856)
7077:ÎČ-Methylphenethylamine
7072:4-Methylphenethylamine
7067:3-Methylphenethylamine
7062:2-Methylphenethylamine
6760:Carbonyl sulfide (COS)
6361:N-Methylphenethylamine
5410:Typical antipsychotics
2858:10.3748/wjg.v12.i4.615
2529:European Pharmacopoeia
2322:10.1124/mol.116.104752
2309:Molecular Pharmacology
1918:is missing information
1891:, drug sensitization,
1522:release of histamine,
1502:central nervous system
1145:central nervous system
994:
927:
815:
7057:MDMA (midomafetamine)
6983:Synthetic and natural
6912:-Methylphenethylamine
6501:2-AGE (noladin ether)
5376:dosulepin (dothiepin)
4496:Histamine MS Spectrum
4417:(2 Part 1): 350â353.
3159:10.1124/pr.114.010249
2522:"Histamine phosphate"
2401:10.2340/00015555-2146
2175:Histamine intolerance
2104:interstitial cystitis
2062:Histamine intolerance
1778:positively correlated
1723:Further information:
1719:Sleep-wake regulation
1701:from glandular tissue
1621:Brain: Produces fast
1552:Located primarily on
1518:functions: decreased
1416:hippocampal formation
1338:endocrine homeostasis
992:
918:
805:
747:of the side-chain is
685:inflammatory response
7301:List of trace amines
7037:4-Hydroxyamphetamine
6712:Carbon monoxide (CO)
4050:Drug Discovery Today
2959:10.1155/2018/9524075
2763:10.3390/ijms20030737
2610:Analytical Chemistry
2237:Analytical Chemistry
2190:Photic sneeze reflex
1952:erectile dysfunction
1851:Gastric acid release
1837:receptor antagonists
1805:histamine receptor H
844:around 9.4) will be
822:centres, namely the
735:ring attached to an
7262:Neutral antagonists
7248:-Dimethylethylamine
7207:Neutral antagonists
7149:Neutral antagonists
7052:MDA (tenamfetamine)
7042:Isopropyloctopamine
6717:Hydrogen sulfide (H
6571:Virodhamine (O-AEA)
4757:Dexchlorpheniramine
4570:2-Pyridylethylamine
4270:10.1007/164_2017_22
3307:2019NatSR...9.3899S
2580:10.1021/jm00298a025
2122:. By 1913 the name
1867:molecules, such as
1824:second-generation H
1812:bloodâbrain barrier
1469:bloodâbrain barrier
1414:(external layers),
1352:bronchoconstriction
1320: •
1281:: Expressed on the
1241:
1226:histamine receptors
1217:Mechanism of action
985:Storage and release
971:scombroid poisoning
932:degradative enzymes
806:The tele tautomer (
489:Solubility in water
462: g·mol
39:
6946:Phenylethanolamine
6774:Sulfur dioxide (SO
6685:Cholinergic system
6387:Phenylethanolamine
6366:N-Methyltryptamine
6330:NAS (normelatonin)
6117:inhibitory systems
6115:Major excitatory /
4822:Homochlorcyclizine
4752:Dexbrompheniramine
4541:Histamine receptor
4411:Journal of Urology
4358:Journal of Urology
3754:10.1007/bf00212757
3742:Psychopharmacology
3295:Scientific Reports
2798:Medical Hypotheses
2704:Digestive Diseases
2671:10.1038/tp.2017.87
2126:was in use, using
2008:multiple sclerosis
2002:Multiple sclerosis
1883:Protective effects
1774:neural firing rate
1758:axonal projections
1628:secretory diarrhea
1473: •
1459: •
1427: •
1394: •
1346: •
1299: •
1277: •
1239:
1124:gluten sensitivity
1110:at the tip of the
1097:ulcerative colitis
1035:attached to their
995:
940:-methyltransferase
928:
818:Histamine has two
816:
705:connective tissues
618:Infobox references
502:in other solvents
37:
7386:Neurotransmitters
7338:
7337:
7333:
7319:
7303:
7291:
7290:
7283:3-Iodothyronamine
7220:
7219:
7183:
7182:
7175:EPPTB (RO5212773)
7143:
7142:
6904:3-Methoxytyramine
6899:3-Iodothyronamine
6790:
6789:
6786:
6785:
6734:
6733:
6726:Nitric oxide (NO)
6700:
6699:
6673:
6661:
6660:
6657:
6656:
6607:
6606:
6603:
6602:
6474:
6473:
6470:
6469:
6442:
6441:
6356:3-Iodothyronamine
6294:
6293:
6098:Neurotransmitters
6064:
6063:
6034:
6033:
5962:α-Methylhistamine
5957:4-Methylhistamine
5933:
5932:
5756:α-Methylhistamine
5732:
5731:
5501:
5500:
5450:Unknown/unsorted:
5308:hydroxynefazodone
4614:First-generation:
4279:978-3-319-58192-7
4001:10.5414/ALX02269E
3950:Leukemia Research
3858:Neuropharmacology
3592:978-0-12-374947-5
3526:978-0-323-47978-3
2716:10.1159/000171249
2622:10.1021/ac071306s
2441:Nelson Biology 12
2358:10.1111/aap.12037
2270:Marieb E (2001).
2249:10.1021/ac102614v
1972:corpus cavernosum
1945:
1944:
1791:First-generation
1788:(non-REM) sleep.
1639:Roles in the body
1636:
1635:
1603:
1315:, sensory nerves
1260:
1223:G protein-coupled
717:white blood cells
626:Chemical compound
624:
623:
333:CompTox Dashboard
121:Interactive image
16:(Redirected from
7403:
7381:Immunostimulants
7324:
7309:
7298:
7276:Inverse agonists
7231:
7194:
7167:Inverse agonists
6849:
6840:
6817:
6810:
6803:
6794:
6765:Nitrous oxide (N
6736:
6705:Gasotransmitters
6702:
6682:
6626:
6619:
6586:
6521:Anandamide (AEA)
6489:Endocannabinoids
6486:
6453:
6340:Serotonin (5-HT)
6305:
6124:Glutamate system
6121:
6112:
6091:
6084:
6077:
6068:
5974:
5947:
5788:
5746:
5557:
5515:
5434:prochlorperazine
5301:Phenylpiperazine
4917:Phenyltoloxamine
4777:Diphenylpyraline
4697:Chlorphenoxamine
4592:
4560:
4534:
4527:
4520:
4511:
4484:
4483:
4473:
4441:
4435:
4434:
4408:
4400:
4394:
4393:
4391:
4389:
4364:(4): 1145â1148.
4349:
4343:
4342:
4340:
4338:
4298:
4292:
4291:
4253:
4247:
4246:
4244:
4243:
4223:
4217:
4216:
4184:
4178:
4177:
4175:
4173:
4133:
4127:
4126:
4124:
4122:
4082:
4076:
4075:
4065:
4041:
4035:
4028:
4022:
4012:
3980:
3974:
3973:
3945:
3939:
3938:
3928:
3896:
3890:
3889:
3853:
3847:
3846:
3815:
3809:
3808:
3780:
3774:
3773:
3737:
3728:
3727:
3709:
3681:
3675:
3674:
3646:
3640:
3639:
3603:
3597:
3596:
3581:Brady S (2012).
3578:
3572:
3571:
3561:
3537:
3531:
3530:
3515:Abbas A (2018).
3512:
3506:
3505:
3495:
3463:
3457:
3456:
3438:
3432:
3431:
3429:
3427:
3422:on 21 March 2017
3403:
3397:
3396:
3378:
3346:
3337:
3336:
3326:
3286:
3280:
3279:
3269:
3259:
3235:
3229:
3228:
3218:
3194:
3181:
3180:
3170:
3138:
3119:
3118:
3108:
3076:
3070:
3069:
3059:
3027:
3018:
3017:
2988:
2982:
2981:
2971:
2961:
2937:
2931:
2930:
2896:
2887:
2881:
2880:
2870:
2860:
2836:
2830:
2829:
2792:
2786:
2785:
2775:
2765:
2737:
2728:
2727:
2699:
2693:
2692:
2682:
2650:
2641:
2640:
2639:on 19 July 2011.
2638:
2632:. Archived from
2607:
2598:
2592:
2591:
2563:
2557:
2556:
2554:
2553:
2547:
2541:. Archived from
2531:(5th ed.).
2526:
2518:
2512:
2511:
2496:
2490:
2489:
2487:
2486:
2477:. Archived from
2475:webbook.nist.gov
2467:
2461:
2460:
2444:
2434:
2428:
2427:
2425:
2424:
2418:
2403:
2385:
2376:
2370:
2369:
2341:
2335:
2334:
2324:
2300:
2294:
2293:
2277:
2267:
2261:
2260:
2231:
2222:
2221:
2208:
1940:
1937:
1931:
1911:
1903:
1770:sleep-wake cycle
1731:neurotransmitter
1688:mucous membranes
1615:
1613:chloride channel
1610:
1601:
1547:
1520:neurotransmitter
1495:
1388:
1330:body temperature
1326:Sleep-wake cycle
1271:
1258:
1249:
1242:
1163:and maintaining
1108:epithelial cells
923:to histamine by
899:
898:
784:aqueous solution
703:found in nearby
681:neurotransmitter
650:neurotransmitter
648:and acting as a
608:
602:
599:
598:
580:
570:
461:
446:
440:
434:
427:Chemical formula
357:
356:
341:
339:
323:
303:
292:
281:
264:
244:
225:
214:
203:
183:
163:
143:
123:
99:
56:
47:
40:
21:
18:Histamine agents
7411:
7410:
7406:
7405:
7404:
7402:
7401:
7400:
7356:Biogenic amines
7341:
7340:
7339:
7334:
7322:
7320:
7318:for references.
7306:
7304:
7287:
7271:
7257:
7216:
7202:
7179:
7161:
7139:
7110:Propylhexedrine
7092:Norfenfluramine
7082:Methamphetamine
6978:
6920:-Methyltyramine
6829:
6821:
6791:
6782:
6777:
6768:
6754:
6730:
6720:
6696:
6653:
6599:
6575:
6466:
6438:
6422:
6344:
6300:Biogenic amines
6290:
6267:
6216:
6190:
6116:
6100:
6095:
6065:
6060:
6030:
5989:
5972:
5942:
5929:
5803:
5786:
5741:
5728:
5567:
5555:
5510:
5497:
5304:antidepressants
4837:Isopromethazine
4772:Diphenhydramine
4657:Brompheniramine
4602:
4590:
4555:
4546:
4538:
4492:
4487:
4443:
4442:
4438:
4402:
4401:
4397:
4387:
4385:
4351:
4350:
4346:
4336:
4334:
4300:
4299:
4295:
4280:
4255:
4254:
4250:
4241:
4239:
4225:
4224:
4220:
4186:
4185:
4181:
4171:
4169:
4136:Tham R (1966).
4135:
4134:
4130:
4120:
4118:
4084:
4083:
4079:
4043:
4042:
4038:
3989:Allergol Select
3982:
3981:
3977:
3947:
3946:
3942:
3898:
3897:
3893:
3855:
3854:
3850:
3817:
3816:
3812:
3782:
3781:
3777:
3739:
3738:
3731:
3683:
3682:
3678:
3648:
3647:
3643:
3605:
3604:
3600:
3593:
3580:
3579:
3575:
3552:(2): S798-806.
3539:
3538:
3534:
3527:
3514:
3513:
3509:
3465:
3464:
3460:
3453:
3440:
3439:
3435:
3425:
3423:
3411:
3405:
3404:
3400:
3348:
3347:
3340:
3288:
3287:
3283:
3237:
3236:
3232:
3196:
3195:
3184:
3140:
3139:
3122:
3078:
3077:
3073:
3029:
3028:
3021:
2990:
2989:
2985:
2939:
2938:
2934:
2894:
2889:
2888:
2884:
2838:
2837:
2833:
2794:
2793:
2789:
2739:
2738:
2731:
2701:
2700:
2696:
2652:
2651:
2644:
2636:
2605:
2600:
2599:
2595:
2565:
2564:
2560:
2551:
2549:
2545:
2539:
2524:
2520:
2519:
2515:
2498:
2497:
2493:
2484:
2482:
2469:
2468:
2464:
2457:
2436:
2435:
2431:
2422:
2420:
2416:
2383:
2378:
2377:
2373:
2343:
2342:
2338:
2302:
2301:
2297:
2290:
2269:
2268:
2264:
2233:
2232:
2225:
2210:
2209:
2202:
2198:
2160:Diamine oxidase
2151:
2128:combining forms
2112:
2084:neuromodulation
2080:
2071:diamine oxidase
2042:
2034:
2030:
2025:
2021:
2017:
2013:
2004:
1993:
1984:
1977:
1957:
1941:
1935:
1932:
1925:
1912:
1901:
1885:
1878:
1861:
1853:
1842:
1836:
1827:
1821:
1808:
1796:
1729:Histamine is a
1727:
1721:
1671:
1650:
1641:
1625:
1611:
1609:Histamine-gated
1608:
1566:small intestine
1546:
1542:
1500:Located in the
1494:
1490:
1472:
1466:
1426:
1420:dentate nucleus
1412:cerebral cortex
1404:caudate nucleus
1400:Dorsal striatum
1387:
1383:
1368:itch perception
1366:), involved in
1345:
1298:
1295:locus coeruleus
1270:
1266:
1245:
1235:
1231:
1219:
1185:tyrosine kinase
1085:diamine oxidase
1081:
987:
944:diamine oxidase
896:
895:
877:decarboxylation
873:
854:
843:
757:
627:
620:
615:
614:
613: ?)
604:
600:
596:
592:
559:
544:
540:
532:
491:
459:
449:
443:
437:
429:
415:
412:
407:
406:
395:
392:
391:
388:
382:
381:
378:
372:
371:
360:
342:
335:
326:
306:
293:
267:
247:
234:
206:
186:
166:
146:
126:
113:
102:
89:
75:
35:
28:
23:
22:
15:
12:
11:
5:
7409:
7407:
7399:
7398:
7393:
7391:TAAR1 agonists
7388:
7383:
7378:
7373:
7368:
7363:
7358:
7353:
7343:
7342:
7336:
7335:
7308:
7297:
7296:
7293:
7292:
7289:
7288:
7286:
7285:
7279:
7277:
7273:
7272:
7270:
7269:
7265:
7263:
7259:
7258:
7256:
7255:
7253:Trimethylamine
7250:
7237:
7235:
7228:
7222:
7221:
7218:
7217:
7215:
7214:
7210:
7208:
7204:
7203:
7200:
7198:
7191:
7185:
7184:
7181:
7180:
7178:
7177:
7171:
7169:
7163:
7162:
7160:
7159:
7153:
7151:
7145:
7144:
7141:
7140:
7138:
7137:
7132:
7127:
7122:
7117:
7112:
7107:
7099:
7094:
7089:
7084:
7079:
7074:
7069:
7064:
7059:
7054:
7049:
7044:
7039:
7034:
7029:
7024:
7019:
7014:
7002:
6997:
6992:
6986:
6984:
6980:
6979:
6977:
6976:
6975:
6974:
6966:
6958:
6953:
6948:
6943:
6941:Phenethylamine
6938:
6930:
6922:
6914:
6906:
6901:
6891:
6890:
6889:
6884:
6879:
6874:
6869:
6857:
6855:
6846:
6837:
6831:
6830:
6822:
6820:
6819:
6812:
6805:
6797:
6788:
6787:
6784:
6783:
6781:
6780:
6775:
6771:
6766:
6762:
6757:
6752:
6748:
6742:
6740:
6732:
6731:
6729:
6728:
6723:
6718:
6714:
6708:
6706:
6698:
6697:
6695:
6694:
6688:
6686:
6679:
6675:
6674:
6670:
6663:
6662:
6659:
6658:
6655:
6654:
6652:
6651:
6646:
6641:
6635:
6633:
6623:
6616:
6609:
6608:
6605:
6604:
6601:
6600:
6598:
6597:
6589:
6583:
6577:
6576:
6574:
6573:
6568:
6563:
6558:
6553:
6548:
6543:
6538:
6533:
6528:
6523:
6518:
6513:
6508:
6503:
6498:
6492:
6490:
6483:
6476:
6475:
6472:
6471:
6468:
6467:
6465:
6464:
6456:
6450:
6444:
6443:
6440:
6439:
6437:
6436:
6430:
6428:
6424:
6423:
6421:
6420:
6412:
6404:
6399:
6394:
6392:Phenethylamine
6389:
6384:
6376:
6368:
6363:
6358:
6352:
6350:
6346:
6345:
6343:
6342:
6337:
6332:
6327:
6322:
6317:
6311:
6309:
6302:
6296:
6295:
6292:
6291:
6289:
6288:
6283:
6277:
6275:
6269:
6268:
6266:
6265:
6260:
6255:
6250:
6245:
6240:
6235:
6230:
6224:
6222:
6221:Glycine system
6218:
6217:
6215:
6214:
6209:
6204:
6198:
6196:
6192:
6191:
6189:
6188:
6183:
6178:
6173:
6168:
6166:Kynurenic acid
6163:
6158:
6153:
6148:
6143:
6138:
6133:
6127:
6125:
6118:
6109:
6102:
6101:
6096:
6094:
6093:
6086:
6079:
6071:
6062:
6061:
6059:
6058:
6053:
6048:
6043:
6039:
6036:
6035:
6032:
6031:
6029:
6028:
6023:
6018:
6013:
6008:
6003:
5997:
5995:
5991:
5990:
5988:
5987:
5982:
5977:
5969:
5964:
5959:
5953:
5951:
5944:
5940:
5935:
5934:
5931:
5930:
5928:
5927:
5922:
5917:
5912:
5907:
5902:
5897:
5892:
5887:
5885:Iodophenpropit
5882:
5877:
5872:
5867:
5862:
5857:
5852:
5847:
5842:
5837:
5832:
5827:
5822:
5817:
5811:
5809:
5805:
5804:
5802:
5801:
5796:
5791:
5783:
5778:
5773:
5768:
5763:
5758:
5752:
5750:
5743:
5739:
5734:
5733:
5730:
5729:
5727:
5726:
5721:
5716:
5711:
5706:
5701:
5696:
5691:
5686:
5681:
5676:
5671:
5666:
5661:
5656:
5651:
5646:
5641:
5636:
5631:
5626:
5621:
5616:
5611:
5606:
5601:
5596:
5591:
5586:
5581:
5575:
5573:
5569:
5568:
5566:
5565:
5560:
5552:
5547:
5542:
5537:
5532:
5527:
5521:
5519:
5512:
5508:
5503:
5502:
5499:
5498:
5496:
5495:
5490:
5485:
5480:
5475:
5470:
5465:
5460:
5455:
5446:
5445:
5414:chlorpromazine
5407:
5353:
5323:
5298:
5240:
5239:
5234:
5229:
5224:
5219:
5214:
5209:
5204:
5199:
5194:
5189:
5184:
5179:
5174:
5169:
5164:
5159:
5154:
5149:
5144:
5139:
5134:
5129:
5127:Levocetirizine
5124:
5119:
5114:
5109:
5104:
5099:
5094:
5089:
5084:
5079:
5074:
5069:
5067:Clobenztropine
5064:
5059:
5054:
5049:
5044:
5039:
5034:
5029:
5024:
5019:
5014:
5009:
5004:
4999:
4990:
4989:
4984:
4982:Tripelennamine
4979:
4974:
4969:
4964:
4959:
4954:
4949:
4944:
4939:
4934:
4929:
4924:
4919:
4914:
4909:
4904:
4899:
4894:
4889:
4884:
4879:
4874:
4869:
4864:
4859:
4854:
4849:
4844:
4839:
4834:
4829:
4824:
4819:
4817:Histapyrrodine
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4764:
4762:Dimenhydrinate
4759:
4754:
4749:
4744:
4739:
4734:
4732:Cyproheptadine
4729:
4724:
4719:
4714:
4709:
4704:
4699:
4694:
4692:Chlorphenamine
4689:
4684:
4682:Chloropyramine
4679:
4677:Chlorcyclizine
4674:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4610:
4608:
4604:
4603:
4601:
4600:
4595:
4587:
4582:
4577:
4572:
4566:
4564:
4557:
4553:
4548:
4547:
4539:
4537:
4536:
4529:
4522:
4514:
4508:
4507:
4498:
4491:
4490:External links
4488:
4486:
4485:
4436:
4395:
4344:
4293:
4278:
4248:
4218:
4179:
4148:(2): 207â216.
4128:
4077:
4036:
3975:
3940:
3891:
3848:
3810:
3775:
3729:
3676:
3641:
3598:
3591:
3573:
3532:
3525:
3507:
3458:
3451:
3433:
3409:
3398:
3361:(3): 590â604.
3338:
3281:
3230:
3182:
3120:
3071:
3042:(3): 197â205.
3019:
3000:(9): 1108â15.
2983:
2932:
2905:(7): 893â902.
2882:
2831:
2787:
2729:
2694:
2642:
2616:(21): 8162â9.
2593:
2558:
2537:
2513:
2491:
2462:
2455:
2429:
2371:
2336:
2315:(5): 649â673.
2295:
2288:
2262:
2243:(6): 1944â54.
2223:
2199:
2197:
2194:
2193:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2150:
2147:
2111:
2108:
2079:
2076:
2041:
2038:
2032:
2028:
2023:
2019:
2015:
2011:
2003:
2000:
1991:
1983:
1980:
1975:
1955:
1948:Loss of libido
1943:
1942:
1915:
1913:
1906:
1900:
1897:
1884:
1881:
1876:
1859:
1852:
1849:
1840:
1834:
1828:antihistamines
1825:
1819:
1806:
1797:antihistamines
1794:
1720:
1717:
1716:
1715:
1708:and increased
1702:
1695:
1670:
1667:
1649:
1646:
1640:
1637:
1634:
1633:
1631:
1619:
1616:
1605:
1604:
1599:
1596:
1593:
1587:
1586:
1584:
1577:
1550:
1544:
1538:
1537:
1535:
1528:norepinephrine
1516:heteroreceptor
1509:
1498:
1492:
1486:
1485:
1483:
1464:
1456:
1433:parietal cells
1391:
1385:
1379:
1378:
1376:
1317:
1274:
1268:
1262:
1261:
1256:
1253:
1250:
1233:
1229:
1228:, designated H
1218:
1215:
1169:gut microbiome
1122:patients with
1080:
1077:
1009:region of the
986:
983:
919:Conversion of
872:
869:
859:. Since human
852:
841:
756:
753:
632:is an organic
625:
622:
621:
616:
594:
593:
589:standard state
586:
583:
582:
581:) (phosphate)
560:
555:
552:
551:
547:
546:
542:
534:
530:
520:
519:
516:
507:
506:
503:
496:
495:
492:
487:
484:
483:
480:
474:
473:
470:
464:
463:
457:
451:
450:
447:
441:
435:
430:
425:
422:
421:
417:
416:
414:
413:
410:
402:
401:
400:
397:
396:
394:
393:
389:
386:
385:
383:
379:
376:
375:
367:
366:
365:
362:
361:
359:
358:
345:
343:
331:
328:
327:
325:
324:
316:
314:
308:
307:
305:
304:
296:
294:
286:
283:
282:
275:
269:
268:
266:
265:
257:
255:
249:
248:
246:
245:
237:
235:
230:
227:
226:
216:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
168:
167:
165:
164:
156:
154:
148:
147:
145:
144:
136:
134:
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
92:
90:
85:
82:
81:
77:
76:
69:
63:
62:
58:
57:
49:
48:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
7408:
7397:
7394:
7392:
7389:
7387:
7384:
7382:
7379:
7377:
7374:
7372:
7371:Immune system
7369:
7367:
7364:
7362:
7359:
7357:
7354:
7352:
7349:
7348:
7346:
7332:
7331:
7328:
7323:
7317:
7313:
7307:
7302:
7294:
7284:
7281:
7280:
7278:
7274:
7267:
7266:
7264:
7260:
7254:
7251:
7249:
7247:
7243:
7239:
7238:
7236:
7232:
7229:
7227:
7223:
7212:
7211:
7209:
7205:
7199:
7195:
7192:
7190:
7186:
7176:
7173:
7172:
7170:
7168:
7164:
7158:
7155:
7154:
7152:
7150:
7146:
7136:
7133:
7131:
7128:
7126:
7123:
7121:
7118:
7116:
7113:
7111:
7108:
7106:
7104:
7100:
7098:
7095:
7093:
7090:
7088:
7085:
7083:
7080:
7078:
7075:
7073:
7070:
7068:
7065:
7063:
7060:
7058:
7055:
7053:
7050:
7048:
7045:
7043:
7040:
7038:
7035:
7033:
7030:
7028:
7025:
7023:
7020:
7018:
7015:
7013:
7011:
7007:
7003:
7001:
6998:
6996:
6993:
6991:
6988:
6987:
6985:
6981:
6973:
6971:
6967:
6965:
6963:
6959:
6957:
6954:
6952:
6949:
6947:
6944:
6942:
6939:
6937:
6935:
6931:
6929:
6927:
6923:
6921:
6919:
6915:
6913:
6911:
6907:
6905:
6902:
6900:
6897:
6896:
6895:
6892:
6888:
6885:
6883:
6880:
6878:
6875:
6873:
6870:
6868:
6865:
6864:
6863:
6859:
6858:
6856:
6854:
6850:
6847:
6845:
6841:
6838:
6836:
6832:
6828:
6825:
6818:
6813:
6811:
6806:
6804:
6799:
6798:
6795:
6779:
6772:
6770:
6763:
6761:
6758:
6756:
6749:
6747:
6744:
6743:
6741:
6737:
6727:
6724:
6722:
6715:
6713:
6710:
6709:
6707:
6703:
6693:
6692:Acetylcholine
6690:
6689:
6687:
6683:
6680:
6678:Miscellaneous
6676:
6671:
6668:
6664:
6650:
6647:
6645:
6642:
6640:
6637:
6636:
6634:
6631:
6627:
6624:
6620:
6617:
6614:
6610:
6595:
6591:
6590:
6587:
6584:
6582:
6581:Neurosteroids
6578:
6572:
6569:
6567:
6564:
6562:
6559:
6557:
6554:
6552:
6549:
6547:
6544:
6542:
6539:
6537:
6534:
6532:
6529:
6527:
6524:
6522:
6519:
6517:
6514:
6512:
6509:
6507:
6504:
6502:
6499:
6497:
6494:
6493:
6491:
6487:
6484:
6481:
6477:
6462:
6458:
6457:
6454:
6451:
6449:
6448:Neuropeptides
6445:
6435:
6432:
6431:
6429:
6425:
6419:
6417:
6413:
6411:
6409:
6405:
6403:
6400:
6398:
6395:
6393:
6390:
6388:
6385:
6383:
6381:
6377:
6375:
6373:
6369:
6367:
6364:
6362:
6359:
6357:
6354:
6353:
6351:
6347:
6341:
6338:
6336:
6333:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6312:
6310:
6306:
6303:
6301:
6297:
6287:
6284:
6282:
6279:
6278:
6276:
6274:
6270:
6264:
6261:
6259:
6256:
6254:
6251:
6249:
6246:
6244:
6241:
6239:
6236:
6234:
6231:
6229:
6226:
6225:
6223:
6219:
6213:
6210:
6208:
6205:
6203:
6200:
6199:
6197:
6193:
6187:
6184:
6182:
6179:
6177:
6174:
6172:
6169:
6167:
6164:
6162:
6159:
6157:
6154:
6152:
6149:
6147:
6144:
6142:
6139:
6137:
6134:
6132:
6129:
6128:
6126:
6122:
6119:
6113:
6110:
6107:
6103:
6099:
6092:
6087:
6085:
6080:
6078:
6073:
6072:
6069:
6057:
6054:
6052:
6049:
6047:
6044:
6041:
6040:
6037:
6027:
6024:
6022:
6019:
6017:
6014:
6012:
6009:
6007:
6004:
6002:
5999:
5998:
5996:
5992:
5986:
5983:
5981:
5978:
5976:
5970:
5968:
5965:
5963:
5960:
5958:
5955:
5954:
5952:
5948:
5945:
5943:
5936:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5898:
5896:
5893:
5891:
5888:
5886:
5883:
5881:
5878:
5876:
5873:
5871:
5868:
5866:
5863:
5861:
5858:
5856:
5853:
5851:
5848:
5846:
5843:
5841:
5838:
5836:
5833:
5831:
5828:
5826:
5823:
5821:
5818:
5816:
5813:
5812:
5810:
5806:
5800:
5797:
5795:
5792:
5790:
5784:
5782:
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5762:
5759:
5757:
5754:
5753:
5751:
5747:
5744:
5742:
5735:
5725:
5722:
5720:
5717:
5715:
5712:
5710:
5707:
5705:
5702:
5700:
5697:
5695:
5692:
5690:
5687:
5685:
5682:
5680:
5677:
5675:
5672:
5670:
5667:
5665:
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5640:
5637:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5600:
5597:
5595:
5592:
5590:
5587:
5585:
5582:
5580:
5577:
5576:
5574:
5570:
5564:
5561:
5559:
5553:
5551:
5548:
5546:
5543:
5541:
5538:
5536:
5533:
5531:
5528:
5526:
5523:
5522:
5520:
5516:
5513:
5511:
5504:
5494:
5491:
5489:
5486:
5484:
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5454:
5451:
5448:
5447:
5443:
5439:
5435:
5431:
5427:
5423:
5419:
5415:
5411:
5408:
5405:
5401:
5400:protriptyline
5397:
5396:nortriptyline
5393:
5389:
5385:
5381:
5377:
5373:
5369:
5365:
5361:
5360:amitriptyline
5357:
5354:
5351:
5347:
5343:
5339:
5335:
5331:
5327:
5324:
5321:
5320:triazoledione
5317:
5313:
5309:
5305:
5302:
5299:
5296:
5292:
5288:
5284:
5280:
5276:
5272:
5268:
5264:
5263:brilaroxazine
5260:
5259:brexpiprazole
5256:
5252:
5248:
5245:
5242:
5241:
5238:
5235:
5233:
5230:
5228:
5225:
5223:
5220:
5218:
5215:
5213:
5210:
5208:
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5178:
5175:
5173:
5170:
5168:
5165:
5163:
5160:
5158:
5155:
5153:
5150:
5148:
5145:
5143:
5140:
5138:
5135:
5133:
5130:
5128:
5125:
5123:
5122:Levocabastine
5120:
5118:
5115:
5113:
5110:
5108:
5105:
5103:
5100:
5098:
5095:
5093:
5090:
5088:
5085:
5083:
5080:
5078:
5075:
5073:
5072:Desloratadine
5070:
5068:
5065:
5063:
5060:
5058:
5055:
5053:
5050:
5048:
5045:
5043:
5040:
5038:
5035:
5033:
5030:
5028:
5025:
5023:
5020:
5018:
5015:
5013:
5010:
5008:
5005:
5003:
5000:
4998:
4995:
4992:
4991:
4988:
4985:
4983:
4980:
4978:
4975:
4973:
4970:
4968:
4965:
4963:
4962:Thenyldiamine
4960:
4958:
4955:
4953:
4950:
4948:
4947:Pyrrobutamine
4945:
4943:
4940:
4938:
4935:
4933:
4930:
4928:
4925:
4923:
4920:
4918:
4915:
4913:
4910:
4908:
4905:
4903:
4900:
4898:
4895:
4893:
4890:
4888:
4885:
4883:
4880:
4878:
4875:
4873:
4872:Methapyrilene
4870:
4868:
4867:Methafurylene
4865:
4863:
4860:
4858:
4855:
4853:
4850:
4848:
4845:
4843:
4840:
4838:
4835:
4833:
4830:
4828:
4825:
4823:
4820:
4818:
4815:
4813:
4810:
4808:
4805:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4758:
4755:
4753:
4750:
4748:
4745:
4743:
4740:
4738:
4735:
4733:
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4710:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4672:Carbinoxamine
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4620:
4618:
4615:
4612:
4611:
4609:
4605:
4599:
4596:
4594:
4588:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4568:
4567:
4565:
4561:
4558:
4556:
4549:
4545:
4542:
4535:
4530:
4528:
4523:
4521:
4516:
4515:
4512:
4506:
4502:
4499:
4497:
4494:
4493:
4489:
4481:
4477:
4472:
4467:
4463:
4459:
4456:(5): 318â44.
4455:
4451:
4447:
4440:
4437:
4432:
4428:
4424:
4420:
4416:
4412:
4407:
4399:
4396:
4383:
4379:
4375:
4371:
4367:
4363:
4359:
4355:
4348:
4345:
4332:
4328:
4324:
4320:
4316:
4312:
4308:
4304:
4297:
4294:
4289:
4285:
4281:
4275:
4271:
4267:
4263:
4259:
4252:
4249:
4237:
4233:
4229:
4222:
4219:
4214:
4210:
4206:
4202:
4198:
4194:
4190:
4183:
4180:
4167:
4163:
4159:
4155:
4151:
4147:
4143:
4139:
4132:
4129:
4116:
4112:
4108:
4104:
4100:
4096:
4092:
4088:
4081:
4078:
4073:
4069:
4064:
4059:
4055:
4051:
4047:
4040:
4037:
4034:
4032:
4027:
4020:
4016:
4011:
4006:
4002:
3998:
3994:
3990:
3986:
3979:
3976:
3971:
3967:
3963:
3959:
3956:(7): 603â25.
3955:
3951:
3944:
3941:
3936:
3932:
3927:
3922:
3918:
3914:
3910:
3906:
3902:
3895:
3892:
3887:
3883:
3879:
3875:
3871:
3867:
3863:
3859:
3852:
3849:
3845:
3841:
3837:
3833:
3829:
3825:
3821:
3814:
3811:
3806:
3802:
3798:
3794:
3790:
3786:
3779:
3776:
3771:
3767:
3763:
3759:
3755:
3751:
3747:
3743:
3736:
3734:
3730:
3725:
3721:
3717:
3713:
3708:
3703:
3699:
3695:
3691:
3687:
3680:
3677:
3672:
3668:
3664:
3660:
3656:
3652:
3645:
3642:
3637:
3633:
3629:
3625:
3621:
3617:
3614:(6): 637â72.
3613:
3609:
3602:
3599:
3594:
3588:
3584:
3577:
3574:
3569:
3565:
3560:
3555:
3551:
3547:
3543:
3536:
3533:
3528:
3522:
3518:
3511:
3508:
3503:
3499:
3494:
3489:
3485:
3481:
3478:(5): 318â44.
3477:
3473:
3469:
3462:
3459:
3454:
3448:
3444:
3437:
3434:
3421:
3417:
3413:
3402:
3399:
3394:
3390:
3386:
3382:
3377:
3372:
3368:
3364:
3360:
3356:
3352:
3345:
3343:
3339:
3334:
3330:
3325:
3320:
3316:
3312:
3308:
3304:
3300:
3296:
3292:
3285:
3282:
3277:
3273:
3268:
3263:
3258:
3253:
3249:
3245:
3241:
3234:
3231:
3226:
3222:
3217:
3212:
3209:(1): 155â68.
3208:
3204:
3200:
3193:
3191:
3189:
3187:
3183:
3178:
3174:
3169:
3164:
3160:
3156:
3153:(3): 601â55.
3152:
3148:
3144:
3137:
3135:
3133:
3131:
3129:
3127:
3125:
3121:
3116:
3112:
3107:
3102:
3098:
3094:
3090:
3086:
3082:
3075:
3072:
3067:
3063:
3058:
3053:
3049:
3045:
3041:
3037:
3033:
3026:
3024:
3020:
3015:
3011:
3007:
3003:
2999:
2995:
2987:
2984:
2979:
2975:
2970:
2965:
2960:
2955:
2951:
2947:
2943:
2936:
2933:
2928:
2924:
2920:
2916:
2912:
2908:
2904:
2900:
2893:
2886:
2883:
2878:
2874:
2869:
2864:
2859:
2854:
2851:(4): 615â20.
2850:
2846:
2842:
2835:
2832:
2827:
2823:
2819:
2815:
2811:
2807:
2803:
2799:
2791:
2788:
2783:
2779:
2774:
2769:
2764:
2759:
2755:
2751:
2747:
2745:
2736:
2734:
2730:
2725:
2721:
2717:
2713:
2709:
2705:
2698:
2695:
2690:
2686:
2681:
2676:
2672:
2668:
2664:
2660:
2656:
2649:
2647:
2643:
2635:
2631:
2627:
2623:
2619:
2615:
2611:
2604:
2597:
2594:
2589:
2585:
2581:
2577:
2574:(4): 689â92.
2573:
2569:
2562:
2559:
2548:on 2015-01-04
2544:
2540:
2534:
2530:
2523:
2517:
2514:
2509:
2505:
2504:Sigma-Aldrich
2501:
2495:
2492:
2481:on 2018-04-27
2480:
2476:
2472:
2466:
2463:
2458:
2456:0-17-625987-2
2452:
2448:
2443:
2442:
2433:
2430:
2415:
2411:
2407:
2402:
2397:
2393:
2389:
2382:
2375:
2372:
2367:
2363:
2359:
2355:
2351:
2347:
2340:
2337:
2332:
2328:
2323:
2318:
2314:
2310:
2306:
2299:
2296:
2291:
2289:0-8053-4989-8
2285:
2281:
2276:
2275:
2266:
2263:
2258:
2254:
2250:
2246:
2242:
2238:
2230:
2228:
2224:
2219:
2215:
2214:
2207:
2205:
2201:
2195:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2152:
2148:
2146:
2143:
2141:
2140:
2135:
2134:
2129:
2125:
2121:
2117:
2116:Henry H. Dale
2109:
2107:
2105:
2099:
2096:
2091:
2087:
2085:
2077:
2075:
2072:
2066:
2063:
2059:
2057:
2056:
2051:
2047:
2039:
2037:
2009:
2001:
1999:
1997:
1996:antipsychotic
1989:
1988:schizophrenia
1982:Schizophrenia
1981:
1979:
1973:
1969:
1965:
1961:
1953:
1949:
1939:
1929:
1923:
1919:
1916:This section
1914:
1910:
1905:
1904:
1898:
1896:
1894:
1890:
1882:
1880:
1875:, block the H
1874:
1870:
1866:
1857:
1850:
1848:
1846:
1838:
1829:
1817:
1813:
1809:
1802:
1798:
1789:
1787:
1783:
1779:
1775:
1771:
1767:
1763:
1759:
1755:
1751:
1748:known as the
1747:
1743:
1740:
1736:
1732:
1726:
1718:
1714:
1711:
1707:
1703:
1700:
1696:
1693:
1692:
1691:
1689:
1685:
1681:
1677:
1668:
1666:
1664:
1660:
1656:
1647:
1645:
1638:
1632:
1629:
1624:
1620:
1617:
1614:
1607:
1606:
1600:
1597:
1594:
1592:
1588:
1585:
1582:
1578:
1575:
1571:
1567:
1563:
1559:
1555:
1551:
1549:
1540:
1539:
1536:
1533:
1529:
1525:
1524:acetylcholine
1521:
1517:
1513:
1510:
1507:
1503:
1499:
1497:
1488:
1487:
1484:
1482:
1480:
1476:
1470:
1462:
1457:
1455:
1454:
1450:
1446:
1442:
1438:
1434:
1431:: Located on
1430:
1425:
1421:
1417:
1413:
1409:
1405:
1401:
1397:
1392:
1390:
1381:
1380:
1377:
1375:
1373:
1369:
1365:
1361:
1357:
1356:smooth muscle
1353:
1349:
1343:
1339:
1335:
1331:
1327:
1323:
1318:
1316:
1314:
1310:
1306:
1305:Smooth muscle
1302:
1296:
1292:
1288:
1284:
1280:
1275:
1273:
1264:
1263:
1257:
1254:
1251:
1248:
1244:
1243:
1237:
1227:
1224:
1216:
1214:
1212:
1211:polymorphisms
1208:
1204:
1199:
1197:
1193:
1189:
1186:
1182:
1178:
1174:
1170:
1166:
1162:
1157:
1154:
1150:
1146:
1141:
1139:
1134:
1130:
1125:
1121:
1117:
1113:
1109:
1104:
1102:
1098:
1094:
1090:
1086:
1078:
1076:
1072:
1070:
1066:
1062:
1058:
1054:
1050:
1046:
1042:
1038:
1034:
1031:
1027:
1022:
1020:
1016:
1012:
1008:
1004:
1000:
991:
984:
982:
980:
976:
972:
968:
963:
961:
957:
953:
949:
945:
941:
939:
933:
926:
922:
917:
913:
911:
908:
905:
901:
893:
889:
886:, a reaction
885:
882:
878:
870:
868:
866:
862:
858:
851:
847:
840:
839:
833:
829:
825:
821:
813:
809:
804:
800:
798:
794:
789:
785:
781:
778:, but not in
777:
773:
769:
766:
762:
754:
752:
750:
746:
742:
739:chain; under
738:
734:
730:
726:
722:
718:
714:
710:
706:
702:
698:
694:
690:
686:
682:
678:
675:
671:
667:
663:
659:
655:
651:
647:
643:
639:
635:
631:
619:
612:
607:
590:
584:
579:
574:
569:
564:
561:
558:
554:
553:
550:Pharmacology
548:
538:
535:
529:
525:
522:
521:
517:
515:
514:
509:
508:
504:
501:
498:
497:
493:
490:
486:
485:
481:
479:
478:Boiling point
476:
475:
471:
469:
468:Melting point
466:
465:
458:
456:
453:
452:
431:
428:
424:
423:
418:
409:
405:
398:
384:
374:
370:
363:
355:
351:
350:DTXSID4023125
347:
346:
344:
334:
330:
329:
322:
318:
317:
315:
313:
310:
309:
302:
298:
297:
295:
289:
285:
284:
280:
276:
274:
271:
270:
263:
259:
258:
256:
254:
251:
250:
243:
239:
238:
236:
233:
229:
228:
224:
220:
217:
215:
213:ECHA InfoCard
210:
209:
202:
198:
197:
195:
193:
190:
189:
182:
178:
177:
175:
173:
170:
169:
162:
158:
157:
155:
153:
150:
149:
142:
138:
137:
135:
133:
130:
129:
122:
118:
117:
115:
111:
106:
105:
98:
94:
93:
91:
88:
84:
83:
78:
73:
68:
64:
59:
55:
50:
46:
41:
33:
19:
7376:Vasodilators
7326:
7325:
7321:
7305:
7245:
7241:
7130:Solriamfetol
7102:
7047:Isoprenaline
7022:Halostachine
7009:
7005:
6969:
6961:
6933:
6925:
6917:
6909:
6894:Trace amines
6871:
6746:Acetaldehyde
6433:
6415:
6407:
6379:
6371:
6349:Trace amines
6016:Thioperamide
5966:
5920:Thioperamide
5860:Clobenpropit
5781:Immethridine
5765:
5684:Ramixotidine
5654:Niperotidine
5619:Isolamtidine
5579:Bisfentidine
5539:
5488:Trelnarizine
5468:Flotrenizine
5449:
5438:thioridazine
5430:perphenazine
5422:fluphenazine
5418:flupenthixol
5404:trimipramine
5368:clomipramine
5364:butriptyline
5350:oxaprotiline
5279:paliperidone
5251:aripiprazole
5243:
5187:Piclopastine
5117:Latrepirdine
5107:Flezelastine
5102:Fexofenadine
5087:Efletirizine
4993:
4987:Triprolidine
4977:Tolpropamine
4972:Thonzylamine
4967:Thiazinamium
4942:Propiomazine
4937:Promethazine
4907:Phenindamine
4887:Orphenadrine
4877:Methdilazine
4842:Isothipendyl
4792:Etodroxizine
4722:Cloperastine
4613:
4579:
4453:
4449:
4439:
4414:
4410:
4398:
4386:. Retrieved
4361:
4357:
4347:
4335:. Retrieved
4310:
4306:
4296:
4261:
4257:
4251:
4240:. Retrieved
4231:
4221:
4196:
4192:
4182:
4170:. Retrieved
4145:
4141:
4131:
4119:. Retrieved
4094:
4090:
4080:
4053:
4049:
4039:
4023:
3992:
3988:
3978:
3953:
3949:
3943:
3911:(1): 24â33.
3908:
3904:
3894:
3864:(3): 180â9.
3861:
3857:
3851:
3843:
3826:(6): 383â7.
3823:
3819:
3813:
3791:(2): 220â4.
3788:
3784:
3778:
3745:
3741:
3692:(2): 183â9.
3689:
3685:
3679:
3654:
3650:
3644:
3611:
3607:
3601:
3582:
3576:
3549:
3545:
3535:
3516:
3510:
3475:
3471:
3461:
3442:
3436:
3424:. Retrieved
3420:the original
3415:
3401:
3358:
3354:
3298:
3294:
3284:
3247:
3243:
3233:
3206:
3202:
3150:
3146:
3091:(6): 802â9.
3088:
3084:
3074:
3039:
3035:
2997:
2993:
2986:
2949:
2945:
2935:
2902:
2898:
2885:
2848:
2844:
2834:
2801:
2797:
2790:
2753:
2749:
2743:
2710:(3): 163â8.
2707:
2703:
2697:
2665:(5): e1126.
2662:
2658:
2634:the original
2613:
2609:
2596:
2571:
2567:
2561:
2550:. Retrieved
2543:the original
2528:
2516:
2503:
2494:
2483:. Retrieved
2479:the original
2474:
2465:
2440:
2432:
2421:. Retrieved
2394:(7): 771â7.
2391:
2387:
2374:
2349:
2345:
2339:
2312:
2308:
2298:
2273:
2265:
2240:
2236:
2212:
2144:
2137:
2131:
2123:
2120:P.P. Laidlaw
2113:
2100:
2092:
2088:
2081:
2067:
2060:
2055:Mastocytosis
2053:
2043:
2005:
1985:
1946:
1936:October 2023
1933:
1917:
1886:
1854:
1814:and produce
1790:
1746:hypothalamus
1742:hypothalamus
1728:
1713:permeability
1706:vasodilation
1684:nasal cavity
1672:
1655:nitric oxide
1651:
1642:
1512:Autoreceptor
1479:gastric acid
1474:
1460:
1458:
1428:
1395:
1393:
1360:vasodilation
1354:, bronchial
1347:
1340:, regulates
1321:
1319:
1300:
1291:dorsal raphe
1278:
1276:
1220:
1207:bronchospasm
1200:
1196:fibromyalgia
1158:
1153:double-blind
1142:
1105:
1082:
1073:
1023:
1007:hypothalamus
996:
964:
951:
937:
929:
874:
849:
837:
817:
811:
807:
799:-histamine.
796:
792:
758:
709:permeability
629:
628:
527:
512:
80:Identifiers
71:
7157:RTI-7470-44
7097:Phentermine
6990:Amphetamine
6936:-Octopamine
6928:-Octopamine
6751:Ammonia (NH
6622:Nucleosides
6382:-Octopamine
6374:-Octopamine
6286:T-HCA (GHC)
6243:Hypotaurine
6195:GABA system
6146:Glutathione
6001:JNJ-7777120
5994:Antagonists
5905:PF-03654746
5900:NNC 38-1049
5895:JNJ-5207852
5880:Impentamine
5845:Betahistine
5808:Antagonists
5761:Cipralisant
5724:Zolantidine
5714:Venritidine
5649:Mifentidine
5594:Dalcotidine
5572:Antagonists
5550:Impromidine
5478:Napactadine
5442:thiothixene
5392:lofepramine
5372:desipramine
5346:mirtazapine
5338:maprotiline
5291:ziprasidone
5287:risperidone
5271:iloperidone
5227:Terfenadine
5222:Temelastine
5172:Olopatadine
5162:Noberastine
5152:Mizolastine
5147:Mebhydrolin
5142:Mapinastine
5132:Linetastine
5047:Carebastine
5032:Bepotastine
5017:Bamirastine
4997:Acrivastine
4957:Thenalidine
4922:Pimethixene
4912:Pheniramine
4897:Oxomemazine
4862:Mequitazine
4852:Medrylamine
4832:Hydroxyzine
4812:Flunarizine
4807:Fenethazine
4802:Etymemazine
4767:Dimetindene
4742:Decloxizine
4717:Clocinizine
4712:Clobenzepam
4702:Cinnarizine
4647:Bepotastine
4622:Alimemazine
4607:Antagonists
4575:Betahistine
4313:: 379â385.
4097:: 379â385.
3995:: 305â314.
3748:(1): 1â14.
3707:11336/80375
3657:(1): 1â15.
3301:(1): 3899.
2952:: 9524075.
2742:"Histamine
2471:"Histamine"
2352:(4): 51â8.
2155:Anaphylaxis
2078:Measurement
1968:risperidone
1833:histamine H
1801:antagonists
1663:anaphylaxis
1558:bone marrow
1556:and in the
1543:Histamine H
1491:Histamine H
1441:neutrophils
1384:Histamine H
1334:nociception
1309:endothelium
1267:Histamine H
1165:homeostasis
1116:enterocytes
1079:Degradation
1065:Antibiotics
1047:. Certain
1041:degranulate
1026:immunologic
993:Mast cells.
904:hydrophilic
765:hygroscopic
745:amino group
713:capillaries
658:spinal cord
634:nitrogenous
541:Terminal NH
420:Properties
219:100.000.092
141:CHEBI:18295
7366:Imidazoles
7345:Categories
7125:Selegiline
7027:Higenamine
7017:Guanfacine
6956:Tryptamine
6951:Synephrine
6860:Classical
6853:Endogenous
6739:Candidates
6613:Nucleobase
6402:Tryptamine
6397:Synephrine
6308:Monoamines
6273:GHB system
6106:Amino acid
6021:Toreforant
6011:Seliforant
5975:-Histidine
5910:Pitolisant
5890:Irdabisant
5875:GSK-189254
5855:Ciproxifan
5850:Burimamide
5794:Methimepip
5789:-Histidine
5709:Tuvatidine
5699:Sufotidine
5694:Roxatidine
5689:Ranitidine
5674:Pibutidine
5669:Oxmetidine
5659:Nizatidine
5639:Lupitidine
5624:Lafutidine
5614:Famotidine
5609:Etintidine
5604:Ebrotidine
5599:Donetidine
5589:Cimetidine
5584:Burimamide
5558:-Histidine
5483:Tagorizine
5473:GSK1004723
5463:Elbanizine
5458:Belarizine
5384:imipramine
5312:nefazodone
5283:quetiapine
5275:olanzapine
5232:Vapitadine
5202:Rupatadine
5182:Pibaxizine
5137:Loratadine
5097:Epinastine
5092:Emedastine
5057:Clemastine
5052:Cetirizine
5042:Cabastinen
5027:Bepiastine
5022:Barmastine
5012:Azelastine
5007:Astemizole
5002:Alinastine
4932:Pipoxizine
4782:Doxylamine
4747:Deptropine
4737:Dacemazine
4707:Clemastine
4687:Chlorothen
4667:Captodiame
4627:Antazoline
4593:-Histidine
4544:modulators
4242:2024-08-18
3452:380557715X
3036:Immunology
2804:: 109738.
2756:(3): 737.
2552:2015-01-04
2538:9287152810
2485:2015-01-04
2423:2024-02-20
2196:References
1964:ranitidine
1960:cimetidine
1889:convulsion
1873:famotidine
1869:ranitidine
1865:Antagonist
1816:drowsiness
1680:mast cells
1581:chemotaxis
1445:mast cells
1424:cerebellum
1313:mast cells
1181:mast cells
1138:probiotics
1033:antibodies
999:mast cells
936:histamine-
907:vasoactive
902:. It is a
881:amino acid
846:protonated
788:tautomeric
755:Properties
749:protonated
737:ethylamine
701:mast cells
500:Solubility
455:Molar mass
321:820484N8I3
232:IUPHAR/BPS
172:ChemSpider
108:3D model (
87:CAS Number
67:IUPAC name
38:Histamine
7351:Histamine
7327:See also:
7120:RO5166017
7032:Hordenine
6972:-Tyramine
6964:-Tyramine
6887:Serotonin
6872:Histamine
6630:Adenosine
6434:Histamine
6418:-Tyramine
6410:-Tyramine
6253:Sarcosine
6233:ÎČ-Alanine
6228:α-Alanine
6006:Mianserin
5967:Histamine
5915:SCH-79687
5870:Enerisant
5865:Conessine
5766:Histamine
5719:Xaltidine
5704:Tiotidine
5664:Osutidine
5644:Metiamide
5629:Lamtidine
5540:Histamine
5525:Amthamine
5493:Trenizine
5388:iprindole
5342:mianserin
5330:amoxapine
5316:trazodone
5267:clozapine
5255:asenapine
5237:Zepastine
5217:Talastine
5207:Setastine
5197:Rocastine
5177:Perastine
5167:Octastine
5157:Moxastine
5112:Ketotifen
5077:Dorastine
5062:Clemizole
5037:Bilastine
4952:Talastine
4927:Piperoxan
4902:Perlapine
4892:Oxatomide
4882:Moxastine
4847:Meclozine
4787:Embramine
4727:Cyclizine
4662:Buclizine
4652:Bromazine
4632:Azatadine
4580:Histamine
4388:18 August
4337:18 August
4226:PubChem.
4172:18 August
4121:18 August
4031:CC BY 4.0
3724:205879131
3412:receptor"
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2826:216303896
2124:histamine
2050:allergies
2040:Disorders
1928:talk page
1845:vigilance
1739:mammalian
1710:capillary
1699:secretion
1554:basophils
1532:serotonin
1475:Periphery
1429:Periphery
1372:urticaria
1350:: Causes
1348:Periphery
1301:Periphery
1283:dendrites
1232:through H
1173:pathogens
1069:polymyxin
1053:alkaloids
1037:membranes
1003:basophils
921:histidine
888:catalyzed
884:histidine
824:aliphatic
733:imidazole
725:pathogens
719:and some
697:basophils
693:pathogens
674:endocrine
630:Histamine
537:Imidazole
411:NCCc1ccn1
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7234:Agonists
7197:Agonists
6867:Dopamine
6844:Agonists
6669:-derived
6615:-derived
6596:instead.
6551:Oleamide
6482:-derived
6463:instead.
6320:Dopamine
6131:Agmatine
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6042:See also
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5820:A-423579
5815:A-349821
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5749:Agonists
5535:Dimaprit
5530:Betazole
5518:Agonists
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5426:loxapine
5334:loxapine
5295:zotepine
5082:Ebastine
4637:Bamipine
4563:Agonists
4480:16993030
4382:Archived
4331:Archived
4327:28715791
4288:28321587
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4236:Archived
4213:32928382
4166:Archived
4115:Archived
4111:28715791
4072:38447930
4033:license.
4019:34651098
3970:11377686
3935:19309354
3878:20493888
3840:15334189
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3671:16890992
3636:10170830
3628:11164999
3502:16993030
3426:20 March
3385:31913658
3333:30846750
3276:22586376
3225:26194403
3177:26084539
3115:25909280
3066:22957768
3014:20551163
2978:30224900
2919:21488903
2877:16489678
2818:32416409
2782:30744146
2689:28485729
2630:17892274
2508:Archived
2414:Archived
2410:26015312
2366:27028114
2331:27563055
2257:21332182
2218:Archived
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1389:receptor
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1120:migraine
1057:morphine
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828:nitrogen
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729:infected
721:proteins
670:autocoid
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557:ATC code
192:DrugBank
161:ChEMBL90
6827:ligands
6667:Vitamin
6561:RVD-Hpα
6516:AA-5-HT
6263:Taurine
6248:Proline
6238:Glycine
6181:Proline
6151:Glycine
5835:AZD5213
5830:ABT-652
5825:ABT-239
5776:Immepip
5563:UR-AK49
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4010:8511827
3926:2697784
3886:7852375
3805:7850330
3762:3133686
3568:9042073
3493:1512903
3376:7099465
3324:6405771
3303:Bibcode
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3106:4742940
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2969:6129797
2899:Allergy
2868:4066097
2773:6386932
2724:2110876
2680:5534955
2588:5452432
2110:History
1799:(i.e.,
1760:to the
1735:neurons
1682:in the
1602:Sources
1508:tissue
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1408:putamen
1259:Sources
1167:in the
1133:alleles
1045:antigen
1019:stomach
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7361:Amines
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1570:spleen
1562:thymus
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1203:asthma
1112:villus
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3882:S2CID
3766:S2CID
3720:S2CID
3632:S2CID
3389:S2CID
2923:S2CID
2895:(PDF)
2822:S2CID
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2546:(PDF)
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