| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
WISTAR RATS, ABOUT 100 G IN WEIGHT, WERE DOSED BY STOMACH TUBE WITH 30 MG OF PURE LINAMARIN (A MAJOR CYANOGENIC GLUCOSIDE IN CASSAVA). NO INTACT LINAMARIN WAS IDENTIFIED IN THE FECES OR BLOOD BUT 5.65 MG WAS EXCRETED IN THE URINE ALONG WITH 0.823 MG OF THIOCYANATE ION. THE AMNIOTIC FLUIDS AND BLOOD SAMPLES OF 40 PREGNANT WOMEN WERE ANALYZED FOR THIOCYANATE. THE CONCENTRATION IN THE AMNIOTIC FLUIDS VARIED FROM 0.66-3.88 MMOL/L WHILE THOSE OF THE BLOOD SAMPLES VARIED FROM 0.70-2.80 MMOL/L. THE HIGHEST CONCENTRATIONS OCCURRED IN THE LOWER CLASS WHO EAT A LOT OF GARI (CASSAVA PUDDING), WHICH IS THE STAPLE DIET THAT CONTAINS THE CYANOGENIC GLYCOSIDE LINAMARIN. THE DETOXIFICATION PRODUCT, THIOCYANATE, SEEMS TO PENETRATE THE PLACENTAL BARRIER. THE IMPLICATION OF THIS IN THE ETIOLOGY OF GOITER AND CRETINISM WAS DISCUSSED. Metabolism / Metabolites THE BIOSYNTHESIS OF LINAMARIN FROM RADIOACTIVE VALINE OR ACETONE CYANOHYDRIN BY UDP-GLUCOSE-DEPENDENT KETONE CYANOHYDRIN GLUCOSYLTRANSFERASE IN FLAX SEEDLINGS WAS INHIBITED BY PREINCUBATION OF FLAX SEEDLINGS WITH ISOLEUCINE, THE PRECURSOR OF LOTAUSTRALIN. Upon exposure to enzymes and gut flora in the human intestine, linamarin can decompose to the toxic chemical hydrogen cyanide. This occurs via the enzyme linamarase, which is found in the cell wall of the plant. Chewing of the plant allows the enzyme to contact the linamarin, converting it into acetone cyanohydrin, which then spontaneously decomposes to hydrogen cyanide. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. (L630) 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) |
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| 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) Interactions RATS WERE FED A SEMIPURIFIED DIET PROVIDING 10% CASEIN SUPPLEMENTED WITH METHIONINE FOR 2 WEEKS, AT WHICH TIME SOME ANIMALS RECEIVED THE SAME DIET WITHOUT THE METHIONINE FOR 4 DAYS. ANIMALS THAT RECEIVED LINAMARIN WERE GIVEN A SINGLE ORAL DOSE CONTAINING 500 OR 250 MG/KG BODY WEIGHT. AT THE LOWER LINAMARIN DOSE DIETARY SUPPLEMENTATION WITH METHIONINE APPEARED TO REDUCE INCIDENCES OF CLINICAL TOXICITY SIGNS AND FATALITIES. DIETARY SUPPLEMENTATION WITH METHIONINE PROVIDED SOME PROTECTION AGAINST THE TOXICITY OF THE LOWER LEVEL OF LINAMARIN ADMINISTERED. |
| References | |
| Additional Infomation |
Linamarin is a beta-D-glucoside. It is functionally related to a 2-hydroxy-2-methylpropanenitrile.
Linamarin has been reported in Phaseolus lunatus, Linum narbonense, and other organisms with data available. Linamarin is found in coffee and coffee products. Linamarin occurs in manioc (Manihot utilissimus), flax (Linum usitatissimum), Phaseolus lunatus (butter bean), Trifolium repens (white clover) and other plants. First isloated in 1830. |
| 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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