6078. N-Methylglucamine

Nomenclature

CAS number: 6284-40-8
1-Deoxy-1-(methylamino)-d-glucitol; N-methyl-d-glucamine; meglumine.
C7H17NO5; mol wt 195.21.
C 43.07%, H 8.78%, N 7.18%, O 40.98%.

Description and references

Prepd from d-glucose and methylamine: Karrer, Herkenrath, Helv. Chim. Acta 20, 83 (1937). Efficacy and toxicity in treatment of leishmaniasis: R. G. Muller et al., Arch. Inst. Cardiol. Mex. 52, 155 (1982); P. Bouree et al., Pathol. Biol. 33, 607 (1985). Antileishmanial activity in dogs: W. L. Chapman et al., Am. J. Vet. Res. 45, 1028 (1984).

Chemical structure

Properties

Crystals from methanol, mp 128-129°. Does not polymerize or dehydrate unless heated above 150° for prolonged periods. [α]D18 18.5° (Karrer); [α]D20 23° (Rhne-Poulenc data sheet). Soly (g/100 ml): water at 25°: ≈100; alcohol at 25°: 1.2; alcohol at 70°: 21. pH of 1% aq soln: 10.5. Forms salts with acids and complexes with metals. Salts with alkyl aryl sulfonic acids act as detergents.

Derivative

Antimonate.

Nomenclature

CAS number: 133-51-7
RP-2168; Glucantim (Farmitalia); Glucantime (Specia); Protostib.
C7H17NO5.HSbO3; mol wt 365.98.
C 22.97%, H 4.96%, N 3.83%, O 34.97%, Sb 33.27%.

Properties

Powder. Soly in water about 35% ww. Practically insol in alcohol, ether, chloroform. pH of aq solns 6-7.

Use

In the synthesis of surface active agents, pharmaceuticals, dyes.

Therapeutic Category

Antimonate as antiprotozoal (Leishmania).

Keywords

Antiprotozoal (Leishmania)