Hexanicotol,Philadelphia,US,1962
myo-Inositol Hexanicotinate is an nicotinate conjugate of myo-inositol, an structural basis for a number of secondary messengers.
ChEBI: Inositol hexanicotinate is an inositol nicotinate. It is functionally related to a nicotinic acid.
100 g of nicotinic acid were suspended in 265 ml of distilled and dried
pyridine without stirring. 68 g of phosphorus oxychloride were added dropwise
to this mixture under continual stirring. The temperature of the reactants,
initially at 20°C, was allowed to rise to about 60°C, and this temperature was
maintained for a further 60 minutes. Thereafter 24.5 g of meso-inositol wereadded gradually, the temperature being controlled so that it did not exceed
about 80°C. The reactants were maintained at this temperature for from 2 to
3 hours, and thereafter the reaction mixture was poured into 500 ml of water.
The pyridine salts formed during the reaction readily dissolved, and the mesoinositol hexanicotinate which had formed crystallized out. The ester was
filtered off and washed with water and acetone or alcohol. Finally, the mesoinositol hexanicotinate was dried at 100°C.
The yield was 90%, the melting point of the product was 258°C to 260°C. and
the chlorine content <0.01%.
Hexopal (Sterling
Winthrop); Linodil (Sterling Winthrop); Palohex
(Sterling Winthrop).
Peripheral vascular disease
Hyperlipidaemia
Potentially hazardous interactions with other drugs
Statins: increased risk of myopathy.
Inositol nicotinate is believed to be slowly hydrolysed
to nicotinic acid. The main route of metabolism is then
conversion to N-methylnicotinamide and the 2-pyridone
and 4-pyridone derivatives; nicotinuric acid is also
formed.
Small amounts of nicotinic acid are excreted unchanged
in urine.
