| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Not applicable for the deuterated standard. The parent compound, histamine, is an endogenous amine that acts as a neurotransmitter and regulator of gastric acid secretion, inflammatory responses, and vasodilation. It signals through four G‑protein coupled receptors: H1 (itching, vasodilation, bronchoconstriction), H2 (gastric acid secretion, chronotropy), H3 (presynaptic autoreceptor in CNS), and H4 (chemotaxis of immune cells).
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
Not applicable. Histamine-alpha,alpha,beta,beta-d4 itself is not used for measuring pharmacological activity. It is employed as an internal standard for accurate quantitation of histamine by mass spectrometry. The parent compound histamine is a potent vasodilator, increases capillary permeability, contracts smooth muscle in the gut and bronchi, and stimulates gastric acid secretion. In the CNS, histamine regulates wakefulness and appetite. |
| ln Vivo |
Not applicable. Histamine-alpha,alpha,beta,beta-d4 is used in analytical and metabolic studies as a tracer or as an internal standard. It is not used in vivo for activity assays. The parent compound histamine is involved in anaphylactic reactions and is released from mast cells and basophils. In research, it is used to induce anaphylactic responses in animals, to test antihistamines, or to study gastric acid secretion. For the labeled standard, no in vivo activity is measured.
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| Enzyme Assay |
For analytical method development, Histamine-alpha,alpha,beta,beta-d4 dihydrochloride is used as an internal standard. A stock solution is prepared in methanol, acetonitrile, or water at 1 mg/mL. Calibration standards are prepared by spiking blank biological matrix (e.g., plasma, urine, cell lysates) with known concentrations of unlabeled histamine dihydrochloride (0.1‑1000 ng/mL) and a fixed concentration of the labeled standard (10‑100 ng/mL). For protein precipitation, 3‑5 volumes of acetonitrile containing the internal standard are added to the sample. After centrifugation, the supernatant is evaporated and reconstituted in mobile phase (0.1% formic acid in water/methanol). For derivatization (for GC‑MS or improved LC‑MS sensitivity), samples can be reacted with dansyl chloride, benzyl chloride, or fluorenylmethyloxycarbonyl chloride (FMOC‑Cl). Analysis is performed by LC‑MS/MS in MRM mode, monitoring transitions: for unlabeled histamine, m/z 112 → 95; for histamine-d4, m/z 116 → 99 (or 116 → 116). The peak area ratio (analyte/IS) is plotted against the nominal concentration to generate a calibration curve. For histamine release assays (from mast cells), the labeled compound can be added as a spike to the supernatant to quantify released histamine.
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| Cell Assay |
For studies of histamine release from mast cells or basophils, Histamine-alpha,alpha,beta,beta-d4 dihydrochloride is used as an internal standard. RBL‑2H3 cells (rat basophilic leukemia cells) are seeded in 96‑well plates (50,000 cells/well) in DMEM/10% FBS for 48 h. Cells are sensitized with anti‑DNP IgE (0.5 ug/mL) overnight. The next day, cells are washed and incubated in Tyrode's buffer (or HBSS). To induce degranulation, cells are treated with DNP‑BSA (1‑10 ng/mL) for 30‑60 min. The supernatant is collected, and Histamine-alpha,alpha,beta,beta-d4 (50 ng/mL) is added as an internal standard. The concentration of released histamine is measured by LC‑MS/MS. The percentage of histamine release is calculated. For functional assays, the labeled compound is not used to measure histamine receptor activity. For receptor binding assays, [3H]mepyramine (H1) or [3H]cimetidine (H2) are used with or without unlabeled histamine.
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| Animal Protocol |
For in vivo determination of histamine levels, animals (e.g., male Sprague‑Dawley rats, 200‑300 g) are administered a compound that triggers histamine release (e.g., compound 48/80, antigen challenge in sensitized animals). Blood, plasma, or tissue homogenates (liver, lung, brain) are collected at predetermined time points (e.g., 5, 15, 30, 60 min). Histamine-alpha,alpha,beta,beta-d4 dihydrochloride is used as an internal standard to quantify histamine levels by LC‑MS/MS. The method is used to assess the efficacy of mast cell stabilizers (e.g., cromolyn sodium) or antihistamines. For pharmacokinetic studies of histamine itself, the labeled compound can be administered as a tracer (0.1‑1 mg/kg IV) to measure the clearance and volume of distribution. However, histamine is rapidly metabolized (by diamine oxidase and histamine N‑methyltransferase). For the deuterated standard, the typical use is as an internal standard, not as a test compound.
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| ADME/Pharmacokinetics |
Histamine-alpha,alpha,beta,beta-d4 dihydrochloride (MW 188.09, C5H5D4N3·2HCl) is a stable isotope‑labeled compound with 99 atom% deuterium at the four side‑chain positions. It has the same chemical and physical properties as unlabeled histamine dihydrochloride. Histamine is a polar, water‑soluble amine (pKa ~6.0, 9.8). After injection, histamine has a plasma half‑life of less than 1 minute in humans due to rapid metabolism by diamine oxidase and histamine N‑methyltransferase. It is excreted in urine as metabolites (methylhistamine, imidazoleacetic acid). The deuterated analog is not metabolically altered but is used as an analytical standard.
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| Toxicity/Toxicokinetics |
Histamine-alpha,alpha,beta,beta-d4 dihydrochloride is chemically stable and non‑toxic at the concentrations used as an internal standard (ng/mL levels). Unlabeled histamine dihydrochloride is a potent vasoactive amine and can cause anaphylaxis at high doses. In research settings, the labeled compound is used in very small amounts (ug/kg) as a tracer, which does not produce pharmacological effects. Standard safety precautions for handling organic chemicals should be followed. The compound is not for human use.
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| References | |
| Additional Infomation |
Histamine-alpha,alpha,beta,beta-d4 dihydrochloride (CAS 344299-48-5) is a stable isotope‑labeled internal standard for the quantitative analysis of histamine by LC‑MS/MS. Histamine is an endogenous mediator of allergic and inflammatory responses, a neurotransmitter, and a regulator of gastric acid secretion. The labeled analog has no therapeutic use and is strictly for research and analytical purposes. Storage: powder at -20degC, desiccated, under inert atmosphere.
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| Molecular Formula |
C5H7D4CL2N3
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|---|---|
| Molecular Weight |
188.09
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| Exact Mass |
187.058
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| CAS # |
344299-48-5
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| Related CAS # |
Histamine;51-45-6
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| PubChem CID |
45039382
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| Appearance |
Off-white to light yellow solid powder
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| Melting Point |
83-84ºC
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| LogP |
2.215
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
8
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| Complexity |
64.7
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C([2H])(C1=CN=CN1)C([2H])([2H])N
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| InChi Key |
NTYJJOPFIAHURM-LNLMKGTHSA-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)/i1D2,2D2
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| Chemical Name |
1,1,2,2-tetradeuterio-2-(1H-imidazol-5-yl)ethanamine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| 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: 25 mg/mL (132.92 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.29 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.29 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.29 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3166 mL | 26.5830 mL | 53.1660 mL | |
| 5 mM | 1.0633 mL | 5.3166 mL | 10.6332 mL | |
| 10 mM | 0.5317 mL | 2.6583 mL | 5.3166 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.
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