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| Targets |
Desethylatrazine-d7 is a stable isotope-labeled internal standard. The unlabeled desethylatrazine (DEA) is not a drug but a major environmental metabolite of the herbicide Atrazine. Its primary target in toxicological studies is the endocrine system, particularly the reproductive system. Atrazine and its metabolites (including DEA) are known as endocrine-disrupting chemicals (EDCs). DEA acts as an inhibitor of the enzyme aromatase (CYP19A1), which is responsible for converting androgens to estrogens. By inhibiting aromatase, DEA can reduce estrogen production and increase testosterone levels. This disruption of the hypothalamic-pituitary-gonadal (HPG) axis has been linked to adverse reproductive effects in wildlife. Additionally, DEA has been shown to interact with the dopamine receptor D1 and alter neurotransmitter levels in the brain. The labeled version is used to study these interactions analytically.
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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].
The in vitro biological activity of Desethylatrazine-d7 is presumed to be identical to its unlabeled parent, desethylatrazine (DEA). In vitro studies using human placental microsomes have shown that DEA inhibits the activity of aromatase (CYP19A1) in a concentration-dependent manner, with an IC₅0 value of around 30 uM. In the human adrenocortical carcinoma cell line H295R, treatment with DEA (1-100 uM) altered the expression of steroidogenic genes (e.g., CYP17, CYP21) and disrupted the production of key hormones such as cortisol and aldosterone. Additionally, in rat pituitary cell cultures (GH3), DEA was found to suppress the expression of the prolactin gene. In neuronal cell cultures (e.g., PC12 cells), DEA has been shown to disrupt the dopaminergic system, increasing dopamine release and altering tyrosine hydroxylase activity. Desethylatrazine-d7 is used as an internal standard in LC-MS analysis to accurately quantify DEA concentrations in the culture medium. |
| ln Vivo |
Desethylatrazine-d7 is a stable isotope-labeled internal standard, and the in vivo activity of its unlabeled parent is derived from studies on Atrazine exposure. As the primary metabolite of Atrazine, desethylatrazine (DEA) is found at significant levels in exposed animals. In vivo, in adult male rats, oral exposure to DEA (25-100 mg/kg/day) has been shown to cause decreased testosterone levels, reduced sperm count and motility, and histological changes in the testis and epididymis. These effects are consistent with its mechanism as an endocrine disruptor. In amphibians (e.g., Xenopus laevis), exposure to Atrazine (which is metabolized to DEA) at environmentally relevant concentrations (ppb levels) has been shown to cause gonadal abnormalities and feminization. DEA is not a pharmacologically active substance but is a contaminant of concern. The labeled compound is used as an internal standard in LC-MS for studying the in vivo metabolism and tissue distribution of Atrazine and its metabolites.
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| Enzyme Assay |
A generic non-cell-based assay for Desethylatrazine-d7 involves its use as an internal standard in an isotope dilution mass spectrometry method for water analysis. Prepare a standard stock solution of the unlabeled Desethylatrazine in methanol (1 mg/mL). Prepare a separate stock solution of the internal standard (Desethylatrazine-d7) at the same concentration. Prepare calibration standards by spiking the unlabeled analyte into deionized water to achieve concentrations ranging from 0.01 to 10 ug/L. Add a fixed concentration of the internal standard (e.g., 1 ug/L) to each calibration standard. Also prepare blank and double-blank samples. For sample preparation, pass 500 mL of the water sample through a solid-phase extraction (SPE) cartridge (e.g., Oasis HLB) at a flow rate of 5-10 mL/min. Dry the cartridge under nitrogen for 30 minutes. Elute the analytes with 5 mL of methanol. Evaporate the eluate to near dryness under a gentle stream of nitrogen. Reconstitute the residue in 500 uL of mobile phase. Analyze the samples by LC-MS/MS in positive ion mode. Monitor the mass transitions: m/z 188 → 146 for Desethylatrazine, and m/z 195 → 153 for Desethylatrazine-d7. Generate the calibration curve by plotting the peak area ratio vs. the nominal concentration.
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| Cell Assay |
A standard in vitro cell-based protocol for the unlabeled desethylatrazine (DEA) involves assessing its effects on steroidogenesis in the H295R human adrenocortical carcinoma cell line. Culture H295R cells in DMEM/F12 medium supplemented with 1% ITS+ Premix (insulin, transferrin, selenium), 1% penicillin/streptomycin, and 2.5% Nu-Serum. Seed the cells in 24-well plates at a density of 3×10⁵ cells/well and allow them to attach for 48 hours. Treat the cells with various concentrations of unlabeled DEA (1 nM, 10 nM, 100 nM, 1 uM, 10 uM, 100 uM) or vehicle control (DMSO, final concentration <0.1%) for 48 hours. After treatment, collect the cell culture supernatants. Measure the levels of testosterone, estradiol, cortisol, and aldosterone in the supernatants using commercially available ELISA kits. For validation, add Desethylatrazine-d7 as an internal standard and analyze the same supernatants by LC-MS/MS to quantify the exact concentration of DEA. Additionally, extract total RNA from the cells and perform qRT-PCR to measure the expression of key steroidogenic genes (e.g., CYP19, CYP17, HSD3B2).
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| Animal Protocol |
A typical in vivo protocol for Desethylatrazine-d7 is used to study the endocrine-disrupting effects of its parent compound. Use male Sprague-Dawley rats (200-250 g, n=10 per group). Administer the unlabeled desethylatrazine (DEA) orally (gavage) at doses of 0, 5, 25, or 125 mg/kg/day for 28 consecutive days (subchronic study). Include a control group receiving the vehicle (corn oil). During the study, monitor body weight and water/food consumption daily. At the end of the treatment period, anesthetize the animals and collect blood via cardiac puncture for serum isolation. Euthanize the animals and weigh the reproductive organs (testes, epididymides, prostate, seminal vesicles). Fix one testis and epididymis in Bouin‘s solution for histopathological examination. Use the other testis for sperm count and motility analysis. Measure serum hormone levels (testosterone, estradiol, LH, FSH) using ELISA kits. For toxicokinetic analysis, collect blood samples during the study and use Desethylatrazine-d7 as the internal standard in an LC-MS assay to determine the systemic exposure to DEA.
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| ADME/Pharmacokinetics |
Desethylatrazine-d7 is not a drug, but its unlabeled parent, desethylatrazine (DEA), is an environmental contaminant. The pharmacokinetics of DEA in rats have been studied following oral administration. DEA is rapidly absorbed, reaching peak plasma concentrations (Cmax) within 1-2 hours. It is widely distributed, with the highest concentrations found in the liver and kidneys. The compound has a relatively short elimination half-life of approximately 4-8 hours in rodents. DEA is not extensively metabolized; it can be further dealkylated to di-desethylatrazine (DDA) or conjugated with glutathione. Excretion is primarily renal, with about 60-80% of the dose recovered in the urine within 24 hours. The long-term persistence of DEA in the environment, however, is more notable than its in vivo half-life. Desethylatrazine-d7 is used as an internal standard to accurately quantify DEA in animal PK studies and environmental samples.
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| Toxicity/Toxicokinetics |
Desethylatrazine-d7 is a research-grade compound and not a pharmaceutical. The toxicity profile of its unlabeled parent, desethylatrazine (DEA), is similar to its parent herbicide, Atrazine. DEA is considered to have low acute toxicity; the oral LD₅0 is >3000 mg/kg in rats. The primary toxicological concern is its chronic effect as an endocrine disruptor. Prolonged exposure in animal studies has been linked to reproductive toxicity (decreased fertility, testicular atrophy) and developmental toxicity (delayed puberty). It has also been associated with mammary tumors in female rats, though the relevance to humans is debated. DEA is a known inhibitor of aromatase. It is classified as a potential endocrine-disrupting chemical by the EPA. For laboratory handling, standard safety precautions should be taken (gloves, lab coat), and the compound should be stored in a tightly closed container in a cool, dry, well-ventilated area.
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| References | |
| Additional Infomation |
Desethylatrazine-d7 is the stable isotope-labeled version of desethylatrazine (DEA), the primary environmental degradation product and major metabolite of the herbicide Atrazine. It is intended for research use only as an internal standard for the accurate quantification of DEA and Atrazine in environmental and biological samples by LC-MS/MS. Atrazine is one of the most widely used herbicides in the world for corn and other crops. It is an endocrine-disrupting chemical (EDC) that inhibits aromatase, leading to reproductive and developmental toxicity in wildlife. Due to its persistence in the environment, Atrazine and its metabolites (including DEA) are frequently found in groundwater and drinking water. This labeled compound is essential for environmental monitoring, food safety testing, and toxicokinetic studies to assess human and wildlife exposure to this controversial herbicide.
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| Molecular Formula |
C6H3D7CLN5
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|---|---|
| Molecular Weight |
194.67
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| Exact Mass |
194.106
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| CAS # |
1216649-31-8
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| PubChem CID |
46780290
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
389.6±25.0 °C at 760 mmHg
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| Melting Point |
134-137°C
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| Flash Point |
189.4±23.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.631
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| LogP |
1.5
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
12
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| Complexity |
142
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| Defined Atom Stereocenter Count |
0
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| SMILES |
NC1N=C(Cl)N=C(NC(C([2H])([2H])[2H])([2H])C([2H])([2H])[2H])N=1
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| InChi Key |
DFWFIQKMSFGDCQ-YYWVXINBSA-N
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| InChi Code |
InChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)/i1D3,2D3,3D
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| Chemical Name |
6-chloro-2-N-(1,1,1,2,3,3,3-heptadeuteriopropan-2-yl)-1,3,5-triazine-2,4-diamine
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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) |
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 | 5.1369 mL | 25.6845 mL | 51.3690 mL | |
| 5 mM | 1.0274 mL | 5.1369 mL | 10.2738 mL | |
| 10 mM | 0.5137 mL | 2.5684 mL | 5.1369 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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