Size | Price | Stock | Qty |
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100mg |
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250mg |
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500mg |
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1g |
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Purity: ≥98%
Histamine is an organic nitrogen compound and endogenous hormone involved in local immune responses, as well as regulating physiological functions in the gut and acting as a neurotransmitter for the brain, spinal cord, and uterus. Histamine has been regarded as a local hormone since its discovery in 1910 because it is not secreted by the traditional endocrine glands; nevertheless, in more recent times, it has been identified as a central neurotransmitter. Histamine is involved in the inflammatory response and has a central role as a mediator of itching. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues. In order to enable white blood cells and certain proteins to interact with pathogens within infected tissues, histamine increases the permeability of capillaries to these entities. The structure is comprised of an imidazole ring joined to an ethylamine chain, with the side-chain'saminogroup being protonated in a physiological environment.
Targets |
Human Endogenous Metabolite
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ln Vitro |
Human articular chondrocytes in culture proliferate more when histamine is present. Numerous cell types, including chondrocytes, fibroblasts, macrophages, endothelial cells, epithelial cells, and T cells, have been shown to exhibit altered behavior in vitro when exposed to histamine. Additionally, histamine affects the expression of many cytokines' receptors as well as how many of them are produced. Histamine receptor expression allows histamine to control various cellular functions. Histamine stimulates the production of matrix metalloproteinases (MMPs)-13 and -3 (collagenase 3 and stromelysin-1, respectively) by histidine decarboxylase (HAC) in vitro[1].
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ln Vivo |
Histamine is a known contributor to allergic and inflammatory responses and a key regulator of many physiological functions, such as angiogenesis, vasopermeability, and cell proliferation[1]. Histamine causes venula hyperpermeability while dilating the vasculature and boosting blood flow. Changes in the location of vascular endothelial cadherin (VE-cadherin) at the endothelial cell junction are indicative of its disruption of the endothelial barrier formation of venula[3].
Histamine can be used for building animal disease models such as gastrointestinal ulcer models. After intravenous injection of histamine hydrochloride, the maximum concentration and AUC of histamine in liver and liver tumor tissues were higher than those in subcutaneous tissues [4]. Inducing gastrointestinal ulcers [5] 1) Pathogenic principle Histamine can cause an increase in gastric acid secretion, a decrease in mucus production, pancreatic reflux, poor gastric blood flow, and ultimately lead to gastric ulcers. Pressure can also increase gastrointestinal peristalsis, making gastric folds more susceptible to damage when exposed to acid. 2) Specific methods Guinea Pig: male • albino • 360-420 g Administration: 5 mg/kg • i.p. • single dose 3) Indicators of successful construction of gastrointestinal ulcer model The ulcer appears as a dot or elongated shape. After dissection of the model, the ulcer index (length of the lesion) was measured under a microscope to be 3.4 mm. |
Cell Assay |
In 80 cm2 culture flasks, cells are grown to confluence using 10% fetal calf serum (FCS) and Dulbecco's modified Eagle's medium (DMEM). At first or second passage, cells are seeded into 96 well culture plates, at densities of approximately 2×103 cells/well. After a day, the cells are treated with either DMEM + 2% FCS on its own (control) or DMEM + 2% FCS plus histamine at a concentration of 1-100 μmol/l (each treatment requiring a minimum of eight wells). Every 48 hours, the medium—containing or not—is replaced, and after six days, the rate of cell growth is calculated.
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Animal Protocol |
New Zealand adult healthy albino rabbits
50, 100, 200 μg/kg
s.c.
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References |
[1]. Ann Rheum Dis . 2003 Oct;62(10):991-4. [2]. Asian Pacific Journal of Tropical Medicine. 2010, 3(2): 112-116. [3]. PLoS One . 2015 Jul 9;10(7):e0132367. [4]. Histamine pharmacokinetics in tumor and host tissues after bolus-dose administration in the rat. Life Sci. 2002 Jan 11;70(8):969-76.[5]. Effects of cimetidine, a histamine H2-receptor antagonist, on various experimental gastric and duodenal ulcers. Am J Dig Dis. 1977 Aug;22(8):677-84. |
Additional Infomation |
Histamine is a member of the class of imidazoles that is 1H-imidazole substituted at position C-4 by a 2-aminoethyl group. It has a role as a human metabolite, a mouse metabolite and a neurotransmitter. It is an aralkylamino compound and a member of imidazoles. It is a conjugate base of a histaminium.
A depressor amine derived by enzymatic decarboxylation of histidine. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. Histamine is a natural product found in Cynanchum caudatum, Phytolacca japonica, and other organisms with data available. Histamine is a metabolite found in or produced by Saccharomyces cerevisiae. An amine derived by enzymatic decarboxylation of HISTIDINE. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter. Histamine stimulates gastric gland secretion, causing an increased secretion of gastric juice of high acidity. This action is probably due mainly to a direct action on parietal and chief gland cells. Absorption: Readily absorbed after parenteral administration. Metabolism / Metabolites: Primarily hepatic. Histamine is rapidly metabolized by methylation and oxidation. Methylation involves ring methylation and catalyzation by the enzyme histamine-N-methyltransferase, producing N-methylhistamine, which is mostly converted to N-methyl imidazole acetic acid. 2 to 3% excreted as free histamine, 4 to 8% as N-methylhistamine, 42 to 47% as N-methyl imidazole acetic acid, 9 to 11% as imidazole acetic acid, and 16 to 23% as imidazole acetic acid riboside. Mechanism of Action: Histamine acts directly on the blood vessels to dilate arteries and capillaries; this action is mediated by both H 1- and H 2-receptors. Capillary dilatation may produce flushing of the face, a decrease in systemic blood pressure, and gastric gland secretion, causing an increased secretion of gastric juice of high acidity. Increased capillary permeability accompanies capillary dilatation, producing an outward passage of plasma protein and fluid into the extracellular spaces, an increase in lymph flow and protein content, and the formation of edema. In addition, histamine has a direct stimulant action on smooth muscle, producing contraction if H 1-receptors are activated, or mostly relaxation if H 2-receptors are activated. Also in humans, the stimulant effect of histamine may cause contraction of the intestinal muscle. However, little effect is noticed on the uterus, bladder, or gallbladder. Histamine has some stimulant effect on duodenal, salivary, pancreatic, bronchial, and lacrimal glands. Histamine also can bind to H3 and H4 receptors which are involved in the CNS/PNS neurotransmitter release and immune system chemotaxis, respectively. |
Molecular Formula |
C5H9N3
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Molecular Weight |
111.1451
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Exact Mass |
310.17
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Elemental Analysis |
C, 73.52; H, 7.14; N, 9.03; O, 10.31
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CAS # |
51-45-6
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Related CAS # |
51-45-6; 56-92-8 (HCl); 51-74-1 (phosphate)
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PubChem CID |
774
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Appearance |
White to yellow solid powder
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Density |
1.1±0.1 g/cm3
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Boiling Point |
331.0±17.0 °C at 760 mmHg
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Melting Point |
83-84ºC
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Flash Point |
180.3±8.1 °C
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Vapour Pressure |
0.0±0.7 mmHg at 25°C
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Index of Refraction |
1.567
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LogP |
-0.92
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tPSA |
54.70
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SMILES |
C1=C(NC=N1)CCN
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InChi Key |
NTYJJOPFIAHURM-UHFFFAOYSA-N
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InChi Code |
InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
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Chemical Name |
2-(1H-imidazol-5-yl)ethanamine
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Synonyms |
LS82-556; LS 82-556; 2-(1H-imidazol-5-yl)ethanamine; 1H-Imidazole-4-ethanamine; Ergamine; Ergotidine; 2-(4-Imidazolyl)ethylamine; 5-Imidazoleethylamine; LS-82-556
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HS Tariff Code |
2934.99.03.00
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO: ~22 mg/mL (~197.9 mM)
Water: ~22 mg/mL Ethanol: ~22 mg/mL |
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Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 8.9969 mL | 44.9843 mL | 89.9685 mL | |
5 mM | 1.7994 mL | 8.9969 mL | 17.9937 mL | |
10 mM | 0.8997 mL | 4.4984 mL | 8.9969 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
NCT00362999 | Active Recruiting |
N/A | Allergic Rhinitis | Children's Mercy Hospital Kansas City |
August 2006 | N/A |
NCT05131555 | Active Recruiting |
Drug: Placebo: Placebo + exercise training. Drug: H1 blockade: H1 receptor antagonist + exercise training |
Exercise Histamine |
University Ghent | August 16, 2021 | Not Applicable |
NCT06152497 | Recruiting | Drug: Placebo Behavioral: Resistance training |
Histamine | University Ghent | September 1, 2023 | Not Applicable |
NCT06154824 | Recruiting | Other: Histamine Other: Cowhage |
Histamine Cowhage |
Aalborg University | December 15, 2023 | Not Applicable |
NCT06081998 | Recruiting | Other: Histamine Other: Cowhage |
Histamine Cowhage Sleep Deprivation |
Aalborg University | November 1, 2023 | Not Applicable |
Effect of histamine on the proliferative rate of HAC in vitro. Ann Rheum Dis . 2003 Oct;62(10):991-4. td> |
Histamine increased blood flow volume. PLoS One . 2015 Jul 9;10(7):e0132367. td> |
L-NAME or phenylephrine pretreatment inhibited histamine-induced hyperpermeability and vascular relaxation. PLoS One . 2015 Jul 9;10(7):e0132367. td> |