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| Other Sizes |
| ln Vitro |
Cyanazine has been shown to be non-genotoxic[1].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Cyazine is rapidly metabolized in rats and dogs and excreted within 4 days. Studies have shown that after oral administration of 14C cyanazine, the substance is rapidly absorbed and metabolized; approximately 40% of the administered dose is excreted in the urine and 47% in the feces. In rats and dogs, cyanazine is rapidly metabolized after oral administration and excreted within approximately 4 days. Metabolism/Metabolites The main metabolic pathway of cyanazine in rats is N-deethylation to form an amine. Additionally, N-acetylcysteine derivatives were detected in the urine. Dechlorination to form 2-hydroxytriazine and cyano hydrolysis to form an amide, followed by further hydrolysis to form a carboxyl analog, were also observed. The 2-hydroxy compound is the main metabolite in the feces. Glutathione conjugates are present in the bile. Red amaranth does not hydroxylate cyanazine but binds to this compound. Hydrolysis, N-dealkylation, and glutathione conjugates were observed in corn. Hydroxy acids and dealkylated hydroxy acids were observed in maize. The carboxyl group on the isopropyl amino side chain inhibited the dealkylation of the ethylamino group. Five days after foliar spraying with 14C cyanazine, water-soluble and chloroform-soluble metabolites were found in millet and foxtail millet. The nitrile group was hydrolyzed, and the triazine ring was hydroxylated at the 2-position. The degradation of cyanazine proceeds first via hydrolysis of the nitrile group, followed by a slower hydrolysis of the 2-chloro group. 2-Hydroxycyanazine was the major metabolite found in rat feces. Rats also produced 4-amino and N-acetylcysteine derivatives and hydrolyzed the cyanide group to the corresponding amide and carboxyl derivatives. Organic nitriles are converted to cyanide ions in the liver by cytochrome P450 enzymes. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is primarily metabolized to thiocyanate by thiocyanate esterase or 3-mercaptopyruvate thiotransferase. Cyanide metabolites are excreted in the urine. (L96) |
| Toxicity/Toxicokinetics |
Toxicity Summary
Organic nitriles can decompose into cyanide ions both in vivo and in vitro. Therefore, the main toxic mechanism of organic nitriles is the production of toxic cyanide ions, or hydrogen cyanide. Cyanide ions are inhibitors of cytochrome c oxidase in the fourth electron transport chain complex (located on the mitochondrial membrane of eukaryotic cells). It forms a complex with the ferric atom in this enzyme. The binding of cyanide ions to this cytochrome prevents electrons from being transferred from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted, and the cell can no longer perform aerobic respiration to produce ATP for energy. Tissues that rely primarily on aerobic respiration, such as the central nervous system and the heart, are particularly susceptible to this. Cyanide can also exert some toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydrocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinate dehydrogenase, and copper/zinc superoxide dismutase. Cyanide binds to the iron ions in methemoglobin to form inactive methemoglobin cyanide. (L97) Toxicity Data LCLo (Rat)> 4,900 mg/m3 Non-human Toxicity Values Oral LD50 in rats: 288 mg/kg Dermal LD50 in rabbits: <2000 mg/kg Oral LD50 in mice: 380 mg/kg Dermal LD50 in rats: >1200 mg/kg For more complete non-human toxicity data for cyanazines (out of 16), please visit the HSDB record page. |
| References | |
| Additional Infomation |
Depending on state or federal labeling requirements, cyanazine may be developmentally toxic. Cyanazine is a colorless crystalline powder, non-corrosive when dry, and is used as a selective systemic herbicide. Cyanazine is a chloro-1,3,5-triazine, formed by substituting 2-chloro-1,3,5-triazine at positions 6 and 4 with ethylamino and (2-cyanopropyl-2-yl)amino groups, respectively. It is both a herbicide and an environmental pollutant and exogenous substance. It is a 1,3,5-triazinylaminonitrile, and also a chloro-1,3,5-triazine. Cyanazine is marketed by DuPont Chemicals under the trade name Bladex and has been used since 1971. In the 1990s, it was the fourth most commonly used synthetic chemical pesticide in US agriculture. Cyanazine is a triazine herbicide used as a pre- and post-emergence herbicide to control annual grasses and broadleaf weeds. It is primarily used on corn, with smaller amounts on cotton, and less than 1% on sorghum and fallow wheat. Due to its teratogenicity and its presence in groundwater, cyanazine is listed as a restricted-use pesticide (RUP) by the U.S. Environmental Protection Agency (EPA). Cyanazine can cause various birth defects in animals over a wide dose range. A long-term study of rats fed cyanazine showed that moderate doses resulted in increased brain weight and decreased kidney weight in third-generation offspring.
Mechanism of Action Photosynthesis inhibitor. |
| Molecular Formula |
C9H13CLN6
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|---|---|
| Molecular Weight |
240.69
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| Exact Mass |
240.089
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| CAS # |
21725-46-2
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| Related CAS # |
Cyanazine-d5;1190003-29-2
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| PubChem CID |
30773
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
349.9±44.0 °C at 760 mmHg
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| Melting Point |
167°C
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| Flash Point |
165.4±28.4 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.614
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| LogP |
0.2
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
16
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| Complexity |
272
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MZZBPDKVEFVLFF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H13ClN6/c1-4-12-7-13-6(10)14-8(15-7)16-9(2,3)5-11/h4H2,1-3H3,(H2,12,13,14,15,16)
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| Chemical Name |
2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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: 100 mg/mL (415.47 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.39 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 (10.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1547 mL | 20.7736 mL | 41.5472 mL | |
| 5 mM | 0.8309 mL | 4.1547 mL | 8.3094 mL | |
| 10 mM | 0.4155 mL | 2.0774 mL | 4.1547 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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