Inositol nicotinate Property

Melting point:

254-256 °C(lit.)

Boiling point:

755.54°C (rough estimate)

Density 

1.3348 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Aqueous Acid (Slightly, Heated), DMSO (Slightly, Heated, Sonicated)

pka

3.92±0.10(Predicted)

form 

Solid

color 

White to Off-White

Merck 

13,5002

InChI

InChI=1S/C42H30N6O12/c49-37(25-7-1-13-43-19-25)55-31-32(56-38(50)26-8-2-14-44-20-26)34(58-40(52)28-10-4-16-46-22-28)36(60-42(54)30-12-6-18-48-24-30)35(59-41(53)29-11-5-17-47-23-29)33(31)57-39(51)27-9-3-15-45-21-27/h1-24,31-36H/t31-,32-,33-,34+,35-,36-

InChIKey

MFZCIDXOLLEMOO-GYSGTQPESA-N

SMILES

[C@@H]1(OC(C2=CC=CN=C2)=O)[C@@H](OC(C2=CC=CN=C2)=O)[C@H](OC(C2=CC=CN=C2)=O)[C@@H](OC(C2=CC=CN=C2)=O)[C@H](OC(C2=CC=CN=C2)=O)[C@@H]1OC(C1=CC=CN=C1)=O

LogP

3.945 (est)

CAS DataBase Reference

6556-11-2(CAS DataBase Reference)

EPA Substance Registry System

Inositol nicotinate (6556-11-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

NM7535400

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Inositol nicotinate Chemical Properties,Usage,Production

Originator

Hexanicotol,Philadelphia,US,1962

Uses

benzidine substitute

Uses

myo-Inositol Hexanicotinate is an nicotinate conjugate of myo-inositol, an structural basis for a number of secondary messengers.

Definition

ChEBI: Inositol hexanicotinate is an inositol nicotinate. It is functionally related to a nicotinic acid.

Manufacturing Process

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%.

brand name

Hexopal (Sterling Winthrop); Linodil (Sterling Winthrop); Palohex (Sterling Winthrop).

Therapeutic Function

Vasodilator

Clinical Use

Peripheral vascular disease

Hyperlipidaemia

Drug interactions

Potentially hazardous interactions with other drugs
Statins: increased risk of myopathy.

Metabolism

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.