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| ln Vitro |
Cyanazine has been shown to be non-genotoxic[1].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Cyanazine is rapidly metabolized and eliminated from the body by rats and dogs (within 4 days). Research showed that after the oral administration of (14)C cyanazine the material was absorbed and metabolized rapidly; about 40% of the administered dose was excreted in the urine and 47% in the feces. In rats and dogs, following oral administration, cyanazine is rapidly metabolized and eliminated within approximately 4 days. Metabolism / Metabolites The primary pathway for metabolism of cyanazine in rats is N-deethylation to yield an amine. In addition, N-acetylcysteinyl derivatives were found in the urine. Dechlorination resulting in a 2-hydroxy triazine was noted, as well as the cyano group hydrolyzed to an amide and then further to a carboxyl analog. The 2-hydroxy compound was a major metabolite in the feces. The bile contained glutathione conjugates. Redroot pigweed did not hydroxylate cyanazine but did conjugate this compound. In corn, hydrolysis, N-dealkylation and glutathione /conjugation/ were observed. The hydroxy-acid and dealkylated hydroxy-acid were observed in corn. Presence of the carboxyl group on the isopropylamino side chain suppressed dealkylation of the ethylamino group. Fall panicum and green foxtail contain water and chloroform soluble metabolites 5 days after foliar (14)C cyanazine application. The nitrile group was hydrolyzed and the triazine two position was hydroxylated. Cyanazine degradation proceeds initially by hydrolysis of the nitrile group and slower hydrolysis of the 2-chloro group. 2-Hydroxycyanazine is the major metabolite found in rat feces. The rat also produces the 4-amino derivative and the N-acetylcysteinyl derivative and hydrolyzes the cyano group to the corresponding amide and carboxy derivatives. Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96) |
| Toxicity/Toxicokinetics |
Toxicity Summary
Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) Toxicity Data LCLo (rat) > 4,900 mg/m3 Non-Human Toxicity Values LD50 Rat oral 288 mg/kg LD50 Rabbit dermal <2000 mg/kg LD50 Mouse oral 380 mg/kg LD50 Rat dermal >1200 mg/kg For more Non-Human Toxicity Values (Complete) data for CYANAZINE (16 total), please visit the HSDB record page. |
| References | |
| Additional Infomation |
Cyanazine can cause developmental toxicity according to state or federal government labeling requirements.
Cyanazine appears as colorless crystals. Non corrosive when dry. Used as a selective systemic herbicide. Cyanazine is a chloro-1,3,5-triazine that is 2-chloro-1,3,5-triazine substituted by an ethyl amino and a (2-cyanopropan-2-yl)amino group at positions 6 and 4 respectively. It has a role as a herbicide, an environmental contaminant and a xenobiotic. It is a 1,3,5-triazinylamino nitrile and a chloro-1,3,5-triazine. Cyanazine is sold by DuPont Chemical as Bladex, and has been in use since 1971. In the 1990s it was the fourth most widely used synthetic chemical pesticide in U.S. agriculture. Cyanazine is a triazine herbicide and is used as a pre- and post-emergent herbicide to control annual grasses and broadleaf weeds. It is used mostly on corn, some on cotton, and less than 1% on grain sorghum and wheat fallow. Cyanazine is classified by the EPA as a Restricted Use Pesticide (RUP) because of its teratogenicity and because it has been found in groundwater. Cyanazine can cause a variety of birth defects in animals over a wide range of doses. In a long-term study of rats fed cyanazine, moderate doses resulted in increased brain weights and decreased kidney weights in third generation offspring. Mechanism of Action A 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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