Meglumine

• BPMeglumine
• JPMeglumine
• Ph. Eur.Meglumine
• USP–NFMeglumine

N-Methylglucamine; N-methyl-D-glucamine; 1-deoxy-1-(methylamino)-D-glucitol; megluminum

1-Deoxy-1-(methylamino)-D-glucitol · [6284-40-8]

UNII 6HG8UB2MUY · PubChem CID 8567

C7H17NO5 · 195.21

pH adjuster, buffering agent

Typical concentrations: — · Dosage forms: Sterile (parenteral/ophthalmic)

An organic base used to form water-soluble salts of acidic drugs, notably iodinated and gadolinium-based contrast media and some anti-inflammatory and antimony drugs. It is also used as a pH adjuster and solubiliser in parenteral and oral formulations and as a counter-ion or stabiliser in amorphous solid dispersions. It is used in the stoichiometric amount needed for salt formation or pH control.

A white or slightly yellowish crystalline powder, odourless or nearly so.

Melting point

about 128–132 °C

pKa

≈ 9.5

pH

strongly alkaline (about 10.5–11 for a 1% w/v aqueous solution)

Specific rotation

about −16° to −17° (aqueous solution)

Solubility

freely soluble in water; sparingly soluble in ethanol; practically insoluble in chloroform and ether

Stable. Store in a well-closed container, protected from light.

As a secondary amine it reacts with acids and can take part in Maillard reactions with reducing sugars; it is incompatible with strong oxidising agents. Its alkalinity can promote hydrolysis of base-sensitive drugs.

Prepared by reductive amination of glucose with methylamine (condensation followed by catalytic hydrogenation) and purified by crystallisation.

Regarded as having low toxicity at the levels used, and it has a long history in intravenous contrast media. The solid and concentrated solutions are irritant to the eyes because of their alkalinity.

Observe normal precautions for the quantity handled. Avoid generating dust; eye protection, gloves and a dust mask are recommended.

Included in the FDA Inactive Ingredient Database (intravenous, intramuscular and other injections; oral preparations) and in parenteral medicines licensed in Europe.

Trometamol (tromethamine); diethanolamine; ethanolamine; lysine; arginine.

Meglumine salts are generally very water-soluble and well tolerated, which is why it is preferred to sodium for high-concentration contrast media. When used for in-situ salt formation, control of the drug–base ratio determines both the pH and the physical stability of the product.