| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 100mg | |||
| Other Sizes |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
WISTAR rats weighing approximately 100 grams were administered 30 mg of pure linamarin (the main cyanogenic glycoside in cassava) via gastric tube. Intact linamarin was not detected in feces or blood, but 5.65 mg of linamarin and 0.823 mg of thiocyanate ions were excreted in urine. Thiocyanate was analyzed from amniotic fluid and blood samples of 40 pregnant women. The concentration of this substance in amniotic fluid ranged from 0.66 to 3.88 mmol/L, while the concentration in blood samples ranged from 0.70 to 2.80 mmol/L. The highest concentrations were observed in the lower classes who consumed large amounts of gali (cassava pudding), a staple food containing the cyanogenic glycoside linamarin. The detoxification product thiocyanate appears to be able to cross the placental barrier. This article explores its significance in the etiology of goiter and cretinism. Metabolism/Metabolites The process by which UDP-glucose-dependent ketocyanoglycosyltransferase catalyzes the synthesis of linamarin from radioactive valine or acetone cyanohydrin in flax seedlings is inhibited by pre-incubation of flax seedlings with isoleucine (a precursor to linamarin). Linamarin, upon contact with enzymes and gut microbiota in the human intestine, decomposes into the toxic chemical hydrogen cyanide. This process is catalyzed by linamarinase, present in the plant cell walls.After chewing the plant, the enzymes come into contact with linamarin, converting it into acetone cyanohydrin, which spontaneously decomposes into hydrogen cyanide. Ingested and absorbed linamarin is rapidly excreted in the urine, and the glycoside itself does not appear to have acute toxicity. (L630) Organic nitriles are converted into 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) |
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| 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 produce 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) Interaction Rats were fed a semi-purified diet containing 10% casein and supplemented with methionine for 2 weeks, followed by a 4-day diet without methionine for some animals. Animals receiving linamarin were given a single oral dose of 500 or 250 mg/kg body weight. At lower doses of linamarin, dietary methionine supplementation appeared to reduce the incidence of clinical toxicity and mortality. Dietary methionine supplementation provided some protection against the toxicity of lower doses of linamarin. |
| References | |
| Additional Infomation |
Linamarin is a β-D-glucoside that functions similarly to 2-hydroxy-2-methylpropionitrile. It has been reported to be found in common bean (Phaseolus lunatus), nabonense (Linum narbonense), and other organisms with relevant data. Linamarin is also found in coffee and coffee products. Additionally, it is present in cassava (Manihot utilissimus), flax (Linum usitatissimum), common bean (Phaseolus lunatus), white clover (Trifolium repens), and other plants. Linamarin was first isolated in 1830.
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| Molecular Formula |
C10H17NO6
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|---|---|
| Molecular Weight |
247.247
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| Exact Mass |
247.106
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| CAS # |
554-35-8
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| PubChem CID |
11128
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| Appearance |
White to off-white solid powder
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| Density |
1.41g/cm3
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| Boiling Point |
473.3ºC at 760mmHg
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| Melting Point |
142-143ºC
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| Flash Point |
240ºC
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| Index of Refraction |
1.549
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| LogP |
-1.8
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
17
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| Complexity |
311
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CC(C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
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| InChi Key |
QLTCHMYAEJEXBT-ZEBDFXRSSA-N
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| InChi Code |
InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1
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| Chemical Name |
2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
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| Synonyms |
Phaseolunatin.; Linamarin
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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 | 4.0445 mL | 20.2224 mL | 40.4449 mL | |
| 5 mM | 0.8089 mL | 4.0445 mL | 8.0890 mL | |
| 10 mM | 0.4044 mL | 2.0222 mL | 4.0445 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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