31112-62-6

Metrizamide is a non-ionic contrast agent. In vivo, metrizamide (0.1 ml/kg of a 370 mg I/ml solution) does not induce EEG abnormalities, indicating minimal neurotoxicity in rabbits. It has also been used as a solute in gradient centrifugation applications.

white fine crystalline powder

Amipaque,Winthrop laboratories

Contrasting product

Metrizamide is a X-ray contrast agent related to Metrizoic Acid (M338935). Metrizamide is used as a diagnostic aid (radiopaque medium).

Metrizamide is a X-ray contrast agent related to Metrizoic Acid (M338935). Metrizamide is used as an diagnostic aid (radiopaque medium).

A SUGAR that has a six-membered ring form (five carbon atoms and one oxygen atom).

pyranose: A sugar having a sixmemberedring containing five carbonatoms and one oxygen atom.

1 mole 3-(acetyl-methyl-amino)-2,4,6-triiodo-5-methylamino-benzoic acid was suspended in thionyl chloride and reacted by stirring at 70°C for 16 hours. Excess thionyl chloride was distilled off in vacuum, the residue dissolved in chloroform, cooled in the ice bath, washed with iced water (3x100 ml), saturated sodium bicarbonate solution (3 x 100 ml), 2 N sodium carbonate solution (2 x 100 ml) and finally with water (3 x 100 ml). After drying with CaCl2 the chloroform distilled off and residue dried in vacuum. Yield of 3- acetylamino-5-(acetyl-methyl-amino)-2,4,6-triiodo-benzoyl chloride: 66%; MP: 238°-240°C (the re-crystallization from tetrahydrofuran).
It (0.02 mole) was dissolved in dioxan (120 ml). To the solution was added (25 ml) and NaHCO3 (0.0022 mol). Glucosamine (0.022 mol) was added in portions and reaction mixture left by stirring at room temperature for 24 hours. The solution was evaporated to dryness in vacuum, the residue dissolved in water (500 ml), filtered clear and run through an Amberlite IR120 H+ ion exchange column. The effluent was evaporated to dryness in vacuum resulting in a white crystalline residue. The crude 3-acetylamino-5-Nmethyl-acetylamino-2,4,6-triiodobenzoyl glucosamine was crystallised from isopropanol (charcoal-treated when in solution), dissolved in water and charcoal-treated at 100°C for 20 min. The water was distilled off in vacuum and the white residue dried in vacuum at 70°C. MP: 190°-195°C.

Amipaque (GE Healthcare).

Diagnostic aid

[1] P MALY. Comparison between EEG and observation of rabbit behaviour in evaluation of subarachnoid neurotoxicity of metrizamide.[J]. Acta radiologica: diagnosis, 1986, 27 2: 235-240. DOI: 10.1177/028418518602700219
[2] HSU C H, CARLO D D, CHEN C, et al. Microvortex for focusing, guiding and sorting of particles??[J]. Lab on a Chip, 2008, 12: 2128-2134. DOI: 10.1039/b813434k