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Mecobalamin is one of the most biologically active forms of vitamin B12 in the human body. Its core structural feature lies in the tetra-pyrrole ring system centered around a cobalt ion, with an above-ligand methyl group (-CH3), which makes it a naturally occurring organic metal coenzyme. This unique methyl cobalamin structure enables it to directly participate in key physiological processes in the human body without undergoing complex liver conversion: it is a necessary cofactor for methionine synthase, regulating the re-methylation pathway of homocysteine to maintain cardiovascular and nervous system health, and ensuring the precise synthesis of DNA and myelin phospholipids; at the same time, it participates in a wide range of methylation reactions as a methyl donor, directly influencing epigenetic regulation and neurotransmitter balance. Compared to traditional forms of cyanocobalamin, its superior tissue affinity and penetration ability across the blood-brain barrier enable it to exhibit better efficacy and onset speed in the treatment of diabetic peripheral neuropathy, megaloblastic anemia, and central nervous system degenerative diseases, making it an important active substance in modern neuropharmacology and precision nutrition therapy fields.
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Chemical Formula |
C24H36O5 |
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Exact Mass |
404 |
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Molecular Weight |
405 |
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m/z |
404 (100.0%), 405 (26.0%), 406 (2.7%), 406 (1.0%) |
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Elemental Analysis |
C, 71.26; H, 8.97; O, 19.77 |
Subacute toxicity
After intravenous injection of 0.5, 5.0, and 50.0mg/kg/day for 90 days in dogs, there were no special changes in general symptoms, body weight, blood and organ weight in each treatment group. In histopathological examination, it was found through microscopic observation that eosinophils were added to the skin cells of the renal proximal urinary tubules at a dose of 50.0mg/kg, and an increase in lysosomes was observed through electron microscopy, while no changes were observed in other organs.
Chronic toxicity
After intravenous injection of 0.5, 5.0, and 50.0mg/kg/day for 12 months in dogs, there were no changes in general symptoms, body weight, blood and organ weight in each treatment group. In histopathological examination, it was found through microscopic observation that eosinophilic granules were added to the skin cells on the renal proximal urinary tubules at doses of 5.0mg/kg or higher. An increase in lysosomes was observed through electron microscopy, and an increase in lysosomes in glomerular mesangial cells and hepatic Kupffer cells was also observed in the dose of 50.0mg/kg experiment.
Pharmacopoeia Information
- Take about 1mg of this Mecobalamin, add about 50mg of potassium bisulfate, place it in a crucible, burn until melted, cool, add 3ml of water, boil until dissolved, add 1 drop of phenolphthalein indicator solution, add sodium hydroxide test solution until light red color appears, add 0.5ml of sodium acetate, 0.5ml of dilute acetic acid, and 0.5ml of 0.2% 1-nitroso-2-naphthol-3,6-disulfonic acid sodium solution to appear red or orange red color; Add 0.5ml hydrochloric acid, boil for 1 minute, and the color will not disappear.
- In the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with that of the main peak of the reference solution.
- Avoid light operation. Take appropriate amounts of this product and the reference product, dissolve and dilute them in water to prepare a solution containing approximately 50 μ g per 1ml. Measure the absorption spectrum of the test solution in the wavelength range of 220-550nm using UV visible spectrophotometry (General Rule 0401), which should be consistent with that of the reference solution.
- The infrared absorption spectrum of this product should be consistent with the reference spectrum (spectrum set 732).
inspect
Clarity of solution:
Take 20mg of this product and dissolve it in 10ml of water. The solution should be clear (General Rule 0902, Method 1).
Related substances:
Determined by high-performance liquid chromatography (General Rule 0512). Avoid light operation.
Test solution:
Take an appropriate amount of this product, dissolve it in the mobile phase, and dilute it quantitatively to prepare a solution containing approximately 0.5mg per 1ml.
Reference solution:
Accurately measure 1ml of the test solution, place it in a 100ml volumetric flask, dilute to the mark with mobile phase, and shake well.
System suitability solution:
Take about 5mg of methomyl reference substance, add 5.0ml of 1mol/L hydrochloric acid solution, place in the dark for 1 hour, immediately add 5.0ml of 1mo/L sodium hydroxide solution, and shake well.
Chromatographic conditions:
Use octadecylane bonding gel as the filler (Luna C18 spectrum, 4.6mmx250mm, 5 μ m or equivalent chromatographic column); Using a 0.03mol/L dihydrogen phosphate solution (adjusted to pH 4.5 with 0.2mol/L sodium hydroxide solution or phosphoric acid) - acetonitrile (84:16) as the mobile phase, the detection wavelength is 342nm; The injection volume is 20 μ l.
System suitability requirement:
In the system suitability solution color chart, the retention time of the formamide peak is about 13 minutes, and the separation degree between the formamide peak and the impurity peak with a relative retention time of about 1.16 should be greater than 3.0.
Measurement method:
Precisely measure the test solution and control solution, inject them into the liquid chromatograph, and record the chromatogram until the retention time of the main component color spectrum peak is three times.
Limit:
If there are impurity peaks in the color chart of the test solution, the area of a single impurity peak shall not exceed 0.5 times (0.5%) of the peak area of the control rolling solution soil, and the sum of the areas of each impurity peak shall not exceed 2 times (2.0%) of the main peak area of the control rolling solution.
Moisture content:
Take this product and measure it according to the moisture determination method (General Rule 0832, Method 1). The moisture content should not exceed 12.0%.
Content determination
According to the high-performance liquid chromatography method (General Rule 0512) for determination. Avoid light operation.
Test solution
Take an appropriate amount of this product, weigh it accurately, dissolve it in mobile phase, and dilute it quantitatively to prepare a solution containing approximately 50 μ g per 1ml.
Reference solution
Take an appropriate amount of methomyl reference substance, weigh it accurately, dissolve it in mobile phase, and dilute it quantitatively to prepare a solution containing approximately 50 μ g per 1ml.
Measurement method
Precisely measure the test solution and control solution, inject them into the liquid chromatograph separately, and record the chromatogram. Calculate based on peak area using the external standard method.
The common synthesis methods of Mecobalamin mainly include the following, which are based on the two-step reaction of reduction and methylation of cyanocobalamin. In practical operation, a one pot reaction is often used to complete the synthesis:
Using cyanocobalamin as the raw material, methylcobalamin is prepared by reduction with sodium borohydride and methylation with iodomethane
This method first reacts cyanocobalamin with sodium borohydride in a solvent such as water or methanol for reduction, then adds iodomethane for methylation, and finally obtains methylcobalamin. During the reaction process, factors such as solvent selection, reaction temperature, reaction time, and the proportion of raw materials can all affect the quality and yield of the product.
Preparation of methylcobalamin from cyanocobalamin by reduction with sodium borohydride and methylation with dimethyl sulfate:
Similar to the above method, but using dimethyl sulfate as the methylation reagent in the methylation step. Dimethyl sulfate is also a commonly used methylation reagent that can effectively convert cyanocobalamin to methylcobalamin.
Preparation of methylcobalamin from cyanocobalamin by reduction with sodium borohydride and methylation with methyl toluenesulfonate:
This method also uses cyanocobalamin as the starting material, which is reduced by sodium borohydride and then methylated with methyl p-toluenesulfonate. The choice of this method depends on the availability of methylation reagents and the optimization of reaction conditions.
Preparation of methylcobalamin by reduction of cyanocobalamin with sodium borohydride and methylation with dimethyl carbonate:
Dimethyl carbonate is also a reagent that can be used for methylation, which is used in this method to convert reduced cyanocobalamin to methylcobalamin.
In the presence of cobalt or iron salts, sodium borohydride reduces cyanocobalamin, and then methylation is carried out using trimethyl iodide sulfoxide or trimethyl bromide sulfoxide to prepare methylcobalamin:
This method introduces cobalt or iron salts as catalysts in the reduction reaction, which may help improve the efficiency of the reaction and the purity of the product. The methylation step is carried out using reagents such as trimethyl iodide sulfoxide or trimethyl bromide sulfoxide.
pharmacological action
Mecobalamin is an endogenous coenzyme B12 that participates in the one carbon unit cycle and plays an important role in the methylation reaction of methionine synthesis from homocysteine. Animal experiments have found that this product is easier to enter neuronal organelles than cyanocobalamin, participating in the synthesis of thymidine in brain cells and spinal cord neurons, promoting the utilization of folate and nucleic acid metabolism, and has a stronger effect on promoting nucleic acid and protein synthesis than cyanocobalamin; This product can promote axonal transport function and axonal regeneration, normalize the transport of axonal skeleton protein of sciatic nerve in streptozotocin induced diabetes rats; It has inhibitory effects on drug-induced neurodegeneration, such as those caused by doxorubicin, acrylamide, vincristine, and spontaneous hypertension in rats. In rat tissue culture, it was found that this product can promote phospholipid synthesis and neuronal myelin formation. This product can reduce the delayed synaptic transmission and restore normal function. By increasing the excitability of nerve fibers and inducing the recovery of ultimate plate potential, it can restore acetylcholine levels in the brains of rats fed with choline deficient feed to normal levels.
A mysterious and deadly anemia disease was commonly found in hospitals in many large cities in North America and Europe. The number of red blood cells in their blood was only one-third or less than that of normal people, and various treatment methods were ineffective. They often died within 1-3 years. This disease is called pernicious anemia.
Scientists initially discovered that taking whole liver supplements could control symptoms of pernicious anemia. After 20 years of research, it was not until 1948 that scientists isolated a red crystalline substance from the liver that had the effect of controlling pernicious anemia, named vitamin B12.
Vitamin B12 is a cobalt containing complex, and methylcobalamin is the fourth generation product of vitamin B12. Due to the binding of a methyl group to the central cobalt molecule, it does not need to be activated to directly act as a coenzyme in the process of producing methionine from homocysteine (Hcy).
Japanese scholars successfully synthesized methylcobalamin through chemical synthesis using cyanocobalamin as the starting material. China began production in 2003, generally using cyanocobalamin as the starting material to synthesize methylcobalamin through reduction and methylation reactions. The production processes of various Chinese companies are basically the same.
Common side effects
Gastrointestinal reactions
Gastrointestinal reactions are one of the most common side effects during use. This mainly includes symptoms such as loss of appetite, nausea, vomiting, and diarrhea. These reactions are usually mild, and with prolonged medication, most patients can gradually adapt and alleviate symptoms. However, for patients with more severe symptoms, it may be necessary to adjust the dosage of medication or discontinue observation.
Allergic reactions
Allergic reactions are one of the side effects that require special attention during use. Although the incidence of allergic reactions is low, once they occur, they can lead to serious consequences. The symptoms of allergic reactions may include rash, itching, redness and swelling of the skin, and in severe cases, allergic shock symptoms such as difficulty breathing and decreased blood pressure may even occur. Therefore, before using it, patients should inform their doctors in detail of their allergy history to avoid potential drug allergy risks.
Symptoms of the nervous system
This compound, as an important nutrient for the nervous system, may also cause some neurological symptoms during its use. These symptoms may include headaches, dizziness, fatigue, etc. These symptoms are usually mild, and with prolonged medication, most patients can gradually adapt and alleviate the symptoms. However, for patients with more severe symptoms, they should seek medical attention promptly and consider adjusting their medication regimen.
Mecobalamin, also known as methylcobalamin, is a vitamin B12 derivative that plays a crucial role in maintaining human health. It is a water-soluble vitamin essential for numerous biochemical reactions in the body, particularly those involving the nervous system and red blood cell formation.
Unlike other forms of vitamin B12, such as cyanocobalamin, it is the active, naturally occurring coenzyme form that directly participates in metabolic processes without requiring additional conversion in the body. This makes it highly bioavailable and easily utilized by the cells.
It is vital for DNA synthesis, neuronal function, and the production of myelin, the protective sheath around nerve fibers. It supports healthy nerve conduction and is often prescribed to treat conditions like peripheral neuropathy, where damage to nerves causes pain, numbness, or tingling sensations.
Moreover, it contributes to the formation of red blood cells by aiding in the synthesis of heme, the iron-containing component of hemoglobin. Adequate levels ensure efficient oxygen transport throughout the body, preventing anemia.
Deficiency can lead to neurological impairments, fatigue, weakness, and other health issues. It is commonly supplemented in vegetarian or vegan diets, as vitamin B12 is naturally abundant in animal products.
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