N-Methyl-D-glucamine
[CAS# 6284-40-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: N-Methyl-D-glucamine
• Synonyms: Meglumine
• Molecular Formula: C₇H₁₇NO₅
• Molecular Weight: 195.21
• CAS Registry Number: 6284-40-8
• EC Number: 228-506-9
• SMILES: CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O

Properties

• Melting point: 128-132 °C
• alpha: -16.5 ° (c=10, H2O, on dry sub)
• Water solubility: 100 g/100 mL (25 °C)

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H318-H351-H360-H362
• Safety Statements: P203-P260-P263-P264-P264+P265-P270-P280-P305+P354+P338-P317-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

N-Methyl-D-glucamine, commonly known as **meglumine**, was synthesized in the early 20th century as a derivative of D-glucosamine. The compound emerged from research focused on enhancing the properties of amino sugars. By methylating D-glucosamine, scientists aimed to improve its solubility and stability, making it more versatile for pharmaceutical applications. Meglumine's ability to form stable salts with various acids and its capacity to enhance drug solubility significantly broadened its utility in medicine and industry. Its discovery provided a foundation for developing effective excipients and formulations, marking an important milestone in pharmaceutical chemistry.

Meglumine is widely employed as a solubilizing agent, particularly for enhancing the water solubility of poorly soluble drugs. This is crucial for improving the bioavailability of medications, allowing for better absorption and efficacy. It forms salts with acidic drugs, aiding in their dissolution and making it a key ingredient in formulations of injectable medications and oral solutions. One of the prominent uses of meglumine is in diagnostic imaging. It is used to form salts with iodinated compounds to create contrast media for radiography and CT scans. These contrast agents improve the visibility of internal structures such as blood vessels and organs, facilitating accurate diagnosis of various conditions. Meglumine-based contrast media are essential for high-quality imaging, contributing to more precise and reliable diagnostic outcomes. Beyond solubilization, meglumine acts as a stabilizer and buffering agent in pharmaceutical formulations. It helps maintain the pH and stability of the drug products, ensuring consistent therapeutic effects and prolonging shelf life. Its use in vaccines, ophthalmic solutions, and injectables highlights its role in improving the stability and effectiveness of diverse pharmaceutical products.

In veterinary medicine, meglumine is used in the formulation of various drugs and vaccines for animals. Its solubilizing properties enhance the bioavailability and effectiveness of veterinary medications, aiding in the treatment and prevention of diseases in animals. Meglumine is also involved in veterinary diagnostic products, supporting animal health management and disease monitoring. It is a component in certain veterinary anti-inflammatory and analgesic formulations. By improving the solubility and stability of active ingredients, meglumine contributes to the effective management of pain and inflammation in animals, enhancing their well-being.

Meglumine serves as a buffer agent in ion-exchange chromatography and electrophoresis. Its ability to form stable complexes with various ions aids in the separation and purification of biomolecules, making it valuable for research in biochemistry and molecular biology. Its use in these techniques helps achieve high-resolution separation and analysis of proteins, nucleic acids, and other biomolecules, facilitating advancements in biochemical research. In structural biology, meglumine is used in protein crystallization processes to improve the solubility and crystallization of proteins. This application aids in studying protein structures and functions, supporting research in drug design and molecular biology by providing insights into the molecular architecture of proteins.

In cosmetics, meglumine is utilized in formulations of creams, lotions, and gels. Its solubilizing and stabilizing properties enhance the texture and stability of cosmetic products, improving their effectiveness and consumer appeal. Meglumine is used to enhance the delivery and efficacy of active ingredients in skincare products, contributing to the development of effective and high-quality cosmetic solutions.

References

1984. Pharmacokinetics of GdDTPA/dimeglumine after intravenous injection into healthy volunteers. Physiological chemistry and physics and medical NMR, 16(2).
URL: 6505043

1993. Evaluation of three chemotherapeutic schemes with meglumine antimoniate in the treatment of visceral leishmaniasis in the State of Para, Brazil. Revista do Instituto de Medicina Tropical de Sao Paulo, 35(6).
DOI: 10.1590/s0036-46651993000600019

2002. Contrast. Radiology Sourcebook.
DOI: 10.1007/978-1-59259-287-6_2