Meglumine

Basic Information

Name: Meglumine

CAS No: 1-Deoxy-1-(methylamino)-D-glucitol [6284-40-8]

Functional Categories

Organic base

1. Nonproprietary Names

BP: Meglumine JP: Meglumine PhEur: Meglumine USP: Meglumine

2. Synonyms

Meglumin; meglumina; megluminum; 1-methylamino-1-deoxy-Dglucitol; N-methylglucamine; N-methyl-D-glucamine.

3. Chemical Name & CAS Registry

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

4. Empirical Formula & Molecular Weight

C7H17NO5 195.21

5. Structural Formula

6. Applications

Meglumine is an organic base used as a pH-adjusting agent and solubilizing agent, primarily in the preparation of soluble salts of iodinated organic acids used as X-ray contrast media.

7. Description

Meglumine occurs as a white to slightly yellow-colored crystalline powder; it is odorless or with a slight odor.

8. Pharmacopeial Specifications

See Table I.

9. Typical Properties

Acidity/alkalinity pH = 10.5 (1% w/v aqueous solution). Dissociation constant pKa = 9.5 at 208C Melting point 128–1328C NIR spectra see Figure 1. Osmolarity A 5.02% w/v aqueous solution is iso-osmotic with serum. Solubility Specific rotation [a]D 20 = 16.58 (10% w/v aqueous solution)

10. Stability & Storage

Meglumine does not polymerize or dehydrate unless heated above 1508C for prolonged periods. The bulk material should be stored in a well-closed container in a cool, dry place. Meglumine should not be stored in aluminum containers since it reacts to evolve hydrogen gas; it discolors if stored in containers made from copper or copper alloys. Stainless steel containers are recommended

11. Incompatibilities

Incompatible with aluminum, copper, mineral acids, and oxidizing materials. Differential scanning calorimetry studies suggest meglumine is incompatible with glipizide.(1)

12. Method of Manufacture

Meglumine is prepared by the imination of glucose and monomethylamine, in an alcoholic solution, followed by catalytic hydrogenation.

13. Safety

Meglumine is widely used in parenteral pharmaceutical formulations and is generally regarded as a nontoxic material at the levels usually employed as an excipient. LD50 (mouse, IP): 1.68 g/kg

14. Handling Precautions

Observe normal precautions appropriate to the circumstances and quantity of material handled. Meglumine should be handled in a well-ventilated environment, and eye protection, gloves, and a respirator are recommended. Exposure to meglumine dust should be kept below 10 mg/m3 for total inhalable dust (8-hour TWA) or 5 mg/m3 for respirable dust (8-hour TWA). There is a risk of explosion when meglumine dust is mixed with air.

15. Regulatory Status

Included in the FDA Inactive Ingredients Database (injections; oral tablets). Included in parenteral medicines licensed in the UK.

16. Related Substances

Eglumine. Eglumine Empirical formula C8H19NO5 Molecular weight 209.24 CAS number [14216-22-9] Synonyms 1-Deoxy-1-(ethylamino)-D-glucitol; N-ethylglucamine. Melting point 1388C Comments Eglumine is prepared similarly to meglumine except that monoethylamine is used as the precursor, instead of monomethylamine.

17. Comments

The EINECS number for meglumine is 228-506-9. The PubChem Compound ID (CID) for meglumine is 8567