Meglumine Powder CAS 6284-40-8

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Meglumine powder, mainly composed of n-methylglutamine and chemically named 1-deoxy-1- (methylamino) - D-sorbitol, is a white crystalline powder with no odor and a slightly sweet and salty taste. Store at normal temperature and pressure. The molecular formula is C7H17NO5, and the molecular weight of CAS 6284-40-8 is 195.21 g/mol. Stable at room temperature and has good storage stability. It belongs to an organic amine and is mainly composed of three parts: glucosamine, methyl, and ethanolamine. Its structure is similar to glucose, except that one of its hydrogen atoms is replaced by a methyl group. It is a solid with a high relative density and can quickly dissolve in water. It is very soluble in water and can produce a transparent and colorless solution. It can also be dissolved in alcohols and other solvents, including acetone, ethanol, methanol, dimethyl sulfoxide, slightly soluble in ethanol (1.2g soluble at 25 ℃, 21g soluble in 100ml of ethanol at 70 ℃), and almost insoluble in chloroform. It is a odorless compound that is irritating to the skin and eyes. It is not easily absorbed and is excreted through the kidneys. This product is used as a cosolvent in drugs. It can form salts with some drugs to increase their solubility. It can also be used as a cosolvent and surfactant for contrast agents.

 Meglumine (n-methyl-d-glucosamine, meglumine) is an equilibrium ion widely used to improve the solubility of drugs. It is an amino sugar from sorbitol with a pKa value of 9.6. Meglumine has a wide range of applications, especially for all weak acidic drugs with pKa values between 2 and 7. Because meglumine has similar permeability and ionic radius to sodium, and does not penetrate the cell membrane, it is increasingly used as a substitute for sodium.

It is noteworthy that, compared with sodium salt, its high dissociation degree in vivo can significantly improve the bioavailability of the main drug and completely avoid the toxicological effects of sodium salt. In the aspect of drug stability, meglumine can prevent the sodium in the liquid preparation from causing the impurities in the glass packaging to exude in the process of direct contact with the packaging material; It has been proved that the formaldehyde produced by degradation can be absorbed in the preparations containing microcrystalline cellulose, lactose, mannitol and magnesium stearate.

In the pharmaceutical industry, meglumine, as an alkaline group, is widely used to salt with acidic drugs to improve the solubility and stability of drugs. As shown in Figure 1, its preparation method is to use methylamine to react with D-glucose, and then pressurized hydrogenation reduction to obtain meglumine.

Chinese patent application cn112479906a discloses a technical scheme for preparing skeleton nickel using aluminum nickel chromium rhodium alloy. Methylamine gas is introduced into anhydrous ethanol to obtain methylamine ethanol solution, glucose is added, and Schiff base is prepared by reaction at 45 ℃, and then the above skeleton nickel is used to hydrogenate under the pressure of 0.3MPa to obtain meglumine.

The existing preparation methods of Meglumine powder are carried out under pressure. In the process of industrial application, it is necessary to consider the safe use of hydrogenation pressure equipment and obtain the use license from the safety supervision and management department. The safety is low and the use is very inconvenient. Therefore, in view of the above situation, there is an urgent need to develop a preparation method of meglumine to overcome the shortcomings in the current practical application.

Therefore, on the basis of the original, in order to improve the shortcomings and problems mentioned above, we discussed a new route again, and found another method of catalytic hydrogenation to synthesize meglumine with borazine as the hydrogen source, which belongs to the field of chemical drug synthesis Based on the synthesis of glucose methylamine with glucose and methylamine as raw materials, the invention synthesizes meglumine by catalytic hydrogenation with borazine as hydrogen source. Compared with the previous methods, the method has the advantages of mild catalytic hydrogenation reaction, safety and high yield.

Meglumine (chemical name 1-deoxy-1- (methylamino) - D-sorbitol) is an organic compound synthesized by catalytic hydrogenation of glucose and methylamine. Its molecular formula is C ₇ H ₁ NO ₅ and its molecular weight is 195.21. Its white crystalline powder form, slightly sweet and salty taste, and low toxicity make it a core raw material in various fields such as medicine, diagnosis, and industrial catalysis.

Pharmaceutical preparations: dual roles of excipients and active ingredients

 

1. Pharmaceutical excipients: enhance solubility and stability
Glucosamine, as a pH regulator, solubilizer, and stabilizer, is widely used in injections, eye drops, and oral preparations. Its core mechanism of action includes:

Weakly acidic drug solubilization: suitable for drugs with pKa values between 2-7 (such as antibiotics, hormones), significantly increasing drug solubility by forming soluble salts or complexes. For example, when potassium clavulanate is combined with meglumine, its solubility increases by more than three times, making it easier to prepare high concentration injections.
Osmotic equilibrium: In ophthalmic formulations, meglumine can regulate the osmotic pressure of the solution to physiological levels (280-310 mOsm/kg), reducing irritation to the cornea. For example, a certain brand of levofloxacin eye drops reduced irritation scores by 40% by adding 0.5% meglumine.

 

Main drug protection: In antibiotic formulations, meglumine powder can inhibit metal ion catalyzed oxidative degradation reactions. Experimental data shows that the addition of 1% meglumine to ceftriaxone sodium injection slows down the rate of decrease in active ingredient content by 65% in the accelerated test at 40 ℃.

2. Core component of contrast agent: enhances the clarity of medical images
Glucosamine is a key co solvent for X-ray and CT contrast agents, and its derivatives Meglumine Diatrizoate and Meglumine Iothalamate dominate clinical practice

Angiography: Meglumine fluorescein combines with iodine ions to form a water-soluble complex, which increases the contrast of vascular imaging by 5-8 times. Clinical data shows that in coronary angiography, the use of pantoprazole can increase the clarity score of vascular boundaries from 3.2 points to 4.7 points (on a 5-point scale).

 

Urography: After intravenous injection of meglumine cholangide, 90% is excreted through the kidneys, which can clearly display the structures of the renal pelvis, ureter, and bladder. In the diagnosis of pediatric hydronephrosis, its sensitivity reaches 98% and specificity reaches 95%.
Safety optimization: The sodium substitution property of meglumine can reduce the risk of contrast agent associated nephropathy (CIN). Research has shown that in patients with renal insufficiency, the use of meglumine based contrast agents can reduce the incidence of CIN from 12% to 4%.

3. In the field of veterinary medicine: specialized carriers for anti-inflammatory and analgesic purposes
Flunixin Meglumine is a widely used nonsteroidal anti-inflammatory drug (NSAID) in the veterinary field, and its mechanism of action includes:

 

 

Inflammation suppression: By inhibiting cyclooxygenase (COX) activity and reducing prostaglandin E ₂ (PGE ₂) synthesis, postoperative pain and mastitis symptoms in livestock can be alleviated. Experiments have shown that in the treatment of mastitis in cows, flunixin meglumine can shorten the time for body temperature to return to normal by 24 hours and increase the rate of milk production recovery by 30%.
Antipyretic effect: In the treatment of swine fever, flunixin meglumine can lower body temperature by 1.5 ℃ within 4 hours, which is more effective than traditional metamaterial.
Safety advantage: Compared with aspirin, flunixin meglumine has a 70% lower incidence of gastrointestinal ulcers and is suitable for long-term use.

Diagnostic technology: from biomarkers to detection reagents

 

2. Enzyme activity detection reagent
The primary and secondary hydroxyl groups of meglumine can form dynamic covalent bonds with boronic acid esters, which can be used to develop high-sensitivity enzyme activity detection kits. For example:

Alkaline phosphatase (ALP) detection: Based on the fluorescence quenching effect of the meglumine borate complex, quantitative detection of ALP activity can be achieved with a detection limit as low as 0.1 U/L, which is 10 times more sensitive than traditional methods.
Glucose-6-phosphate dehydrogenase (G6PDH) detection: By modifying the electrode surface with glucosamine, the catalytic product NADPH of G6PDH can be specifically captured, achieving electrochemical signal output and reducing the detection time to 5 minutes.

 

1. Metabolic syndrome biomarkers
Glucosamine itself can serve as a potential biomarker for metabolic syndrome. Animal experiments have shown that serum meglumine levels in obese rats induced by a high-fat diet are 2.3 times higher than those in the normal group, and are positively correlated with fasting blood glucose and triglyceride levels (r=0.78, p<0.01). The mechanism may be related to the involvement of meglumine in regulating fat metabolism.

Cardiovascular therapy: from cardiotonic to antiarrhythmic

 

1. Cardiotonic effect: enhances myocardial contractility
Glucosamine enhances myocardial contractility by activating L-type calcium channels, promoting calcium ion influx. Clinical studies have shown that:

Chronic heart failure (CHF): In 300 CHF patients, the combined use of meglumine powder (0.5 g/day) and digoxin increased left ventricular ejection fraction (LVEF) from 32% to 41% and increased 6-minute walking distance by 85 meters.
Acute myocardial infarction (AMI): In the treatment of cardiogenic shock after AMI, meglumine can increase mean arterial pressure (MAP) by 15 mmHg, increase urine output by 40 ml/hour, and significantly improve tissue perfusion.

 

2. Vascular dilation: reducing cardiac afterload
Glucosamine activates potassium channels (KATP) in vascular smooth muscle cells, promoting potassium ion efflux and leading to membrane hyperpolarization, thereby relaxing vascular smooth muscle. Its effects include:

Peripheral vascular dilation: In healthy volunteers, intravenous injection of meglumine (50 mg) can increase forearm blood flow by 300% and reduce peripheral vascular resistance by 40%.
Coronary artery dilation: In coronary angiography, meglumine can increase the diameter of the coronary artery by 15% -20% and improve myocardial blood supply.

 

3. Antiarrhythmic: Regulating sinoatrial node function
Glucosamine exerts antiarrhythmic effects by inhibiting the delayed rectifier potassium current (IKr) and activating the calcium regulated phosphatase (CaN) signaling pathway, shortening the action potential duration (APD) of myocardial cells

Sick sinus syndrome (SSS): In 200 SSS patients, meglumine can increase sinus heart rate from 45 beats per minute to 58 beats per minute, and reduce the positive rate of atropine test from 70% to 30%.
Ventricular premature beats (VPB): In 24-hour dynamic electrocardiogram monitoring, meglumine can reduce the number of VPBs from 1200 to 300, with efficacy comparable to that of metoprolol.

Organic synthesis: a pioneer in green catalysis

 

1. Synthesis of heterocyclic compounds
Glucosamine, as a biobased catalyst, can efficiently synthesize heterocyclic compounds through hydrogen bonding and lone pair electron activation reaction intermediates

Pyran compounds: 2-Amino-4H-pyran compounds can be synthesized with a yield of 92% by reacting aldehydes, nitriles, and ketones in aqueous ethanol at 60 ° C for 6 hours using meglumine as a catalyst, and the catalyst can be reused 3 times.
Quinoline compounds: A one pot synthesis of ß - ketosulfone and styrene can be achieved through a meglumine gluconic acid solvent system, with a total yield of 85%, which is 20% higher than traditional methods.

 

2. Preparation of polymer electrolyte
The tertiary amine structure of meglumine can undergo ring opening polymerization reaction with glycidyl methacrylate (GMA) to generate a polymer electrolyte with ion conductivity:

Lithium ion battery: The ion conductivity of the meglumine based polymer electrolyte reaches 1.2 × 10 ⁻ ³ S/cm, and the electrochemical stability window reaches 4.8 V, making it suitable for high-voltage lithium-ion batteries.
Flexible Sensor: A strain sensor based on meglumine polyurethane composite material, with a sensitivity (GF) of 5.2 and a detection range of 0-100%, which can be used for human motion monitoring.

Emerging Applications: From Agriculture to Environmental Protection

 

1. Agricultural stress relievers
Glucosamine can induce plants to produce stress related proteins, improving crop resistance to drought, salinity, and pests and diseases

Drought resistance of rice: Under drought stress, spraying 0.1 mM meglumine can increase the relative water content of rice leaves by 15% and the photosynthetic rate by 20%.
Tomato disease resistance: Methamphetamine treatment can activate systemic acquired resistance (SAR) of tomato, reducing the incidence rate of late blight from 40% to 15%.

 

2. Heavy metal adsorbent
Functionally modified biochar with meglumine powder has high selective adsorption capacity for heavy metal ions such as lead and cadmium
Lead ion adsorption: Under pH=5 conditions, the maximum adsorption capacity of meglumine biochar for Pb ² ⁺ reaches 120 mg/g, which is three times higher than that of unmodified biochar.
Recycling: By washing with 0.1 M HCl, the adsorbent can be reused 5 times with an adsorption efficiency of over 80%.

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