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Benzyldimethyltetradecylammonium-d7 chloride is a deuterium-labeled quaternary ammonium compound. The non-labeled parent compound, benzyldimethyltetradecylammonium chloride (BDMDTAC), is a cationic surfactant that acts by disrupting the lipid bilayers of cell membranes. This compound exhibits broad-spectrum antimicrobial activity against bacteria, fungi, and enveloped viruses. Its mechanism of action involves electrostatic interactions between the positively charged quaternary ammonium group and the negatively charged components of the microbial cell membrane, such as phospholipids and lipopolysaccharides. This interaction leads to disruption of the membrane integrity, leakage of intracellular contents, and ultimately cell death. The deuterated version is used solely as an analytical standard and does not engage in biological interactions for therapeutic purposes.
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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].
As a deuterium-labeled internal standard, benzyldimethyltetradecylammonium-d7 chloride itself is not used to assess biological activity in vitro. It is used exclusively for analytical quantification purposes. The non-labeled benzyldimethyltetradecylammonium chloride, however, exhibits antimicrobial activity in vitro against a wide range of microorganisms. In a typical antimicrobial susceptibility assay, the compound demonstrates minimum inhibitory concentrations (MICs) in the range of 1-10 ug/mL against Gram-positive bacteria (e.g., Staphylococcus aureus) and 10-50 ug/mL against Gram-negative bacteria (e.g., Escherichia coli). The compound also exhibits fungicidal activity against Candida albicans and other fungi. The antimicrobial activity is concentration-dependent and is influenced by the presence of organic matter, which can reduce its efficacy. The deuterated version is used as an internal standard to accurately quantify the non-labeled compound in biological or environmental samples. |
| ln Vivo |
Benzyldimethyltetradecylammonium-d7 chloride does not exhibit in vivo biological activity because it is an analytical standard. The non-labeled parent compound, benzyldimethyltetradecylammonium chloride, has been used as a disinfectant and antiseptic in various settings, including healthcare and food processing. In vivo, the compound is a cationic surfactant that can disrupt cell membranes and has been shown to be toxic when ingested or absorbed in significant amounts. It is not used as a systemic therapeutic agent due to its non-specific mechanism of action and potential for systemic toxicity. As an internal standard, the deuterated form may be used in animal studies to enable precise quantification of the non-labeled compound in plasma, tissues, or environmental samples.
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| Enzyme Assay |
A typical non-cellular protocol for using benzyldimethyltetradecylammonium-d7 chloride as an internal standard involves its incorporation into the sample preparation workflow for LC-MS analysis. A stock solution of the internal standard (1 mg/mL) is prepared in methanol or acetonitrile. For environmental water samples, 100 mL of the water sample is filtered through a 0.45 um membrane filter. Then, 100 uL of the internal standard solution (diluted to a working concentration of 1 ug/mL) is added. The sample is loaded onto a solid-phase extraction (SPE) cartridge (e.g., C18 or mixed-mode cation exchange) that has been preconditioned with methanol and water. The cartridge is washed with 5 mL of water, and the analyte is eluted with 5 mL of methanol. The eluate is evaporated to dryness under nitrogen and reconstituted in 200 uL of methanol. The sample (5-10 uL) is injected onto an LC-MS/MS system operated in positive ion mode with multiple reaction monitoring (MRM) for the specific transitions of the target analyte and the deuterated internal standard.
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| Cell Assay |
A typical in vitro cellular protocol for using benzyldimethyltetradecylammonium-d7 chloride as an internal standard involves the quantification of quaternary ammonium compounds in cultured cells. Cells (e.g., 1×10⁶ human hepatocytes or kidney cells) are cultured in appropriate medium for 24 hours. After treatment with test compounds, cells are washed twice with ice-cold PBS and harvested by scraping. Cell pellets are resuspended in 200 uL of PBS, and 10 uL of the internal standard solution (1 ug/mL) is added. Cells are lysed by three freeze-thaw cycles (liquid nitrogen for 3 minutes, then 37degC water bath for 5 minutes). Proteins are precipitated by adding 800 uL of acetonitrile containing 0.1% formic acid. After centrifugation, the supernatant is analyzed by LC-MS/MS. The concentration of quaternary ammonium compounds is normalized to total protein content. The internal standard corrects for extraction efficiency and matrix effects.
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| Animal Protocol |
Benzyldimethyltetradecylammonium-d7 chloride is typically used as an internal standard in animal studies for the quantification of quaternary ammonium compounds in plasma and tissues. In a typical protocol, male Sprague-Dawley rats (200-250 g) are administered the non-labeled test compound via oral gavage or intravenous injection at a dose of 1-10 mg/kg. Blood samples (200 uL) are collected via the tail vein into EDTA-coated tubes at various time points (0, 0.5, 1, 2, 4, 6, 8, 12, 24 hours) post-dose. Plasma is separated by centrifugation (2,000 g, 10 minutes, 4degC). For tissue analysis, rats are euthanized at the final time point, and liver, kidney, and other tissues are harvested, rinsed with PBS, snap-frozen in liquid nitrogen, and stored at -80degC. Tissues are homogenized in PBS (100 mg tissue/1 mL PBS) using a tissue homogenizer. For extraction, 50 uL of plasma or tissue homogenate is mixed with 10 uL of internal standard solution (1 ug/mL) and 200 uL of acetonitrile. After centrifugation, the supernatant is analyzed by LC-MS/MS. The internal standard corrects for variations in sample preparation and matrix effects.
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| ADME/Pharmacokinetics |
As an analytical internal standard, benzyldimethyltetradecylammonium-d7 chloride is not characterized by typical pharmacokinetic parameters. It is not intended to be administered as a test article for PK studies. However, the non-labeled benzyldimethyltetradecylammonium chloride is a cationic surfactant. Its quaternary ammonium structure means it is not well-absorbed orally due to its permanent positive charge, which limits gastrointestinal absorption. If administered intravenously, it is likely to be highly protein-bound and distributed primarily to the liver and kidneys, with minimal central nervous system penetration due to the presence of the blood-brain barrier. The compound is likely metabolized by phase I and phase II enzymes and excreted in both urine and feces. The deuterium-labeled version, when used as an internal standard, is added exogenously to samples and does not contribute to the in vivo PK profile of any test compound.
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| Toxicity/Toxicokinetics |
Toxicity data specific to benzyldimethyltetradecylammonium-d7 chloride are not available. The non-labeled benzyldimethyltetradecylammonium chloride is a quaternary ammonium compound that can be toxic if ingested, inhaled, or absorbed through the skin. It is a skin and eye irritant and may cause respiratory irritation. The compound can be fatal if swallowed and enters the airways. Quaternary ammonium compounds are generally considered toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. Standard laboratory safety precautions must be strictly followed when handling this compound: handle in a well-ventilated fume hood, wear appropriate personal protective equipment (gloves, lab coat, safety goggles), and avoid inhalation, ingestion, and direct skin or eye contact. The compound should be stored in a tightly sealed container in a cool, dry place away from incompatible materials. It is for research use only and should not be used in humans or animals for therapeutic or diagnostic purposes.
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| References | |
| Additional Infomation |
Benzyldimethyltetradecylammonium-d7 chloride (CAS# 1219178-72-9) is a stable isotope-labeled quaternary ammonium compound with a molecular weight of 375.08. The molecular formula is C23H35D7ClN. It is also known as BDMDTAC-d7, dimethyl({[(2,3,4,5,6-2H₅)phenyl](2H2)methyl})tetradecylazanium chloride. The isotopic purity is typically >98%, and the chemical purity is ≥98%. This deuterated quaternary ammonium salt is widely used in various research fields, including as a surfactant in nanoparticle synthesis, drug delivery systems, and as an analytical standard. It is soluble in water and polar organic solvents. This product is for research use only and is not approved for clinical or veterinary applications. The compound should be stored at room temperature or as recommended by the supplier.
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| Molecular Formula |
C23H35D7CLN
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| Molecular Weight |
375.08
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| Exact Mass |
374.345
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| CAS # |
1219178-72-9
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| PubChem CID |
46780728
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| Appearance |
White to off-white solid powder
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| Melting Point |
58-59°C
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| LogP |
3.968
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
25
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| Complexity |
265
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1=C(C(=C(C(=C1[2H])[2H])C([2H])([2H])[N+](C)(C)CCCCCCCCCCCCCC)[2H])[2H].[Cl-]
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| InChi Key |
OCBHHZMJRVXXQK-JKJUCWQGSA-M
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| InChi Code |
InChI=1S/C23H42N.ClH/c1-4-5-6-7-8-9-10-11-12-13-14-18-21-24(2,3)22-23-19-16-15-17-20-23;/h15-17,19-20H,4-14,18,21-22H2,1-3H3;1H/q+1;/p-1/i15D,16D,17D,19D,20D,22D2;
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| Chemical Name |
[dideuterio-(2,3,4,5,6-pentadeuteriophenyl)methyl]-dimethyl-tetradecylazanium;chloride
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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 Note: Please store this product in a sealed and protected environment, 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 2.6661 mL | 13.3305 mL | 26.6610 mL | |
| 5 mM | 0.5332 mL | 2.6661 mL | 5.3322 mL | |
| 10 mM | 0.2666 mL | 1.3330 mL | 2.6661 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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