INOSITOL

''[1]
''myo''-Inositol ''myo''-Inositol
Chemical name
Other names	Cyclohexanehexol, Cyclohexitol, Dambose, Inosital, Inosite, iso-Inositol, Inositene, Inositina, i-Inositol, Inositol, MI, Meat sugar, Mesoinosit, Mesoinosite, meso-Inositol, Mesol, Mesovit, Myoinosite, Mouse antialopecia factor, Nucite, Phaseomannite, Phaseomannitol Rat antispectacled eye factor, and Scyllite (for the structural isomer ''scyllo''-Inositol)
Chemical formula
Molecular mass	g/mol
CAS number	[]
Density	g/cm³
Melting point	°C
SMILES

'Inositol', (of which the most prominent naturally-occurring form is ''myo''-inositol, '''cis''-1,2,3,5-''trans''-4,6-cyclohexanehexol'), is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells, including inositol phosphates, phosphatidylinositol (PI) and phosphatidylinositol phosphate (PIP) lipids. It is found in many foods, particularly in cereals with high bran content, nuts, beans, and fruit, especially cantaloupe melons and oranges. Inositol is not considered a vitamin itself because it is not a vital amine (contains no nitrogen) and is synthesised by the body.
Other naturally occurring isomers (though in minimal quantities) are ''scyllo-'', ''chiro''-, ''muco''-, and ''neo''-inositol. Other possible isomers are ''allo''-, ''epi''- and ''cis''-inositol.
''myo''-Inositol is classified as a member of the vitamin B complex (often referred to as vitamin B8), and is synthesized by the human body.

Contents

Structure

Synthesis

Function

Clinical implications

Illicit uses

See also

References

External links

Structure

The chemical formula of myo-inositol is ₆₁₂₆. In its most stable geometry, the inositol ring is in the chair conformation. There are nine stereoisomers, all of which may be referred to as inositol; however, the natural isomer has a structure in which the 1^st, 3^rd, 4^th, 5^th and 6^th hydroxyls are equatorial, while the 2^nd hydroxyl group is axial.^[2]

Synthesis

''myo''-Inositol is synthesized from glucose-6-phosphate (G-6-P) in two steps. First, G-6-P is isomerised by INYNA1 to ''myo''-inositol 1-phosphate, which is then dephosphorylated by IMPA1 to give ''myo''-inositol.

Function

Inositol as the basis for a number of signalling and secondary messenger molecules, is involved in a number of biological processes, including:

★ insulin signal transduction^[3]

★ cytoskeleton assembly

★ nerve guidance (Epsin)

★ intracellular calcium (Ca²⁺) concentration control

★ cell membrane potential maintenance

★ serotonin activity modulation

★ breakdown of fats and reducing blood cholesterol

★ gene expression ^{[4] [5]}

Clinical implications

Some preliminary results of studies on inositol supplements show promising results for people suffering from problems such as bulimia, panic disorder and bipolar depression.
D-chiro-inositol (DCI) has been found in two double-blind studies to be an effective treatment for many of the clinical hallmarks of polycystic ovary syndrome (PCOS), including insulin resistance, hyperandrogenism and oligo-amenorrhea. ^{[6] [7]} The impetuses for these studies were the observed defects in DCI metabolism in PCOS and the implication of DCI in insulin signal transduction.^{[3] [9]}
''myo-''Inositol has been found in double-blind studies to be an effective treatment for obsessive-compulsive disorder (OCD). It is equal in effectiveness to SSRIs and is virtually free from side effects.^{[10] [11] [12]}
Animal studies suggest inositol reduces the severity of the osmotic demyelination syndrome if given prior to rapid correction of chronic hyponatraemia.^[13] Further study is required prior to its application in humans for this indication.
Studies from ''in vitro'' experiments, animal studies, and limited clinical experiences, claim that inositol may be used effectively against some types of cancer, particularly when used in combination with phytic acid ^{[14] [15]}.

Illicit uses

''myo''-Inositol powder can be used in small proportions as a cutting agent for cocaine or methamphetamine ("crystal meth"). It has an almost identical appearance when in powder form and portrays similar qualities when heated. This, in addition to the fact that it adds almost no discernable taste or feel to either drug regardless the method of use, makes it an ideal cutting agent. Cutting either drug at any point in the distribution increases volume of the street product and increases dealer profits. However, at higher cut levels the inositol becomes somewhat noticeable in that the quality of the product is obviously diminished.

See also

★ Essential nutrient

★ inositol phosphate

★ inositol trisphosphate

★ inositol pentakisphosphate

★ inositol hexaphosphate

★ inositol triphosphate receptor

★ Inositol hexanicotinate

References

1. ''Merck Index'', 11th Edition, '4883'.
2. The Chemical and Bio-physical properties of Phosphatidylinositol phosphates, Thesis for M.Res., S. M. N. Furse, , , Imperial College London, 2006,
3. D-chiro-inositol--its functional role in insulin action and its deficit in insulin resistance, Larner J, , , Int J Exp Diabetes Res, 2002
4. Modulation of ATP-dependent chromatin-remodeling complexes by inositol polyphosphates, , , , Science, 2003

5.
Regulation of chromatin remodelling by inositol polyphosphates, , , , Science, 2003

6. Ovulatory and metabolic effects of D-chiro-inositol in the polycystic ovary syndrome, Nestler J E, Jakubowicz D J, Reamer P, Gunn R D, Allan G, , , N Engl J Med, 1999
7. Effects of d-chiro-inositol in lean women with the polycystic ovary syndrome, Iuorno M J, Jakubowicz D J, Baillargeon J P, Dillon P, Gunn R D, Allan G, Nestler J E, , , Endocr Pract, 2002
8. D-chiro-inositol--its functional role in insulin action and its deficit in insulin resistance, Larner J, , , Int J Exp Diabetes Res, 2002
9. Role of inositolphosphoglycan mediators of insulin action in the polycystic ovary syndrome, Nestler J E, Jakubowicz D J, Iuorno M J, , , J Pediatr Endocrinol Metab, 2000
10. Double-blind, controlled, crossover trial of inositol versus fluvoxamine for the treatment of panic disorder, Palatnik A, Frolov K, Fux M, Benjamin J, , , Journal of Clinical Psychopharmacology, 2001
11. Inositol treatment of obsessive-compulsive disorder, Fux M, Levine J, Aviv A, Belmaker RH, , , American Journal of Psychiatry, 1996
12. Phosphoinositides in cell regulation and membrane dynamics, Di Paolo G, De Camilli P, , , Nature, 2006
13. Myoinositol administration improves survival and reduces myelinolysis after rapid correction of chronic hyponatremia in rats, Silver SM, Schroeder BM, Sterns RH, Rojiani AM, , , J Neuropathol Exp Neurol, 2006
14. http://jn.nutrition.org/cgi/content/full/133/11/3778S
15. http://www.ip-6online.com/articles.html

External links

★ ''Cancer Inhibition by Inositol Hexaphosphate (IP6) and Inositol: From Laboratory to Clinic'' (scientific publication}