Inositol

From Wikipedia, the free encyclopedia

myo-Inositol^[1]

Chemical name	cis-1,2,3,5-trans-4,6-Cyclohexanehexol
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	C₆H₁₂O₆
Molecular mass	180.16 g/mol
CAS number	[87-89-8]
Density	1.752 g/cm³
Melting point	225-227 °C
SMILES	O[C@H]1[C@H](O)[C@@H](O) [C@H](O)[C@H](O)[C@@H]1O
Disclaimer and references

Inositol, (of which the most prominent naturally-ocurring 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.

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, though it is not considered a vitamin itself because it is not a vital amine (contains no nitrogen) and is synthesised by the human body.

1 Structure
2 Synthesis
3 Function
4 Clinical implications
5 Illicit uses
6 See also
7 References
8 External links

[edit] Structure

The chemical formula of myo-inositol is C₆H₁₂O₆. 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]

[edit] 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.

[edit] Function

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

cytoskeleton assembly
nerve guidance (Epsin)
intracellular calcium (Ca²⁺) concentration control
cell membrane potential maintenance
serotonin activity modulation
breakdown of fats and reducing blood cholesterol^{[citation needed]}
gene expression ^[3] ^[4]

[edit] 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.

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.^[5] ^[6] ^[7]

Animal studies suggest inositol reduces the severity of the osmotic demyelination syndrome if given prior to rapid correction of chronic hyponatraemia.^[8] Further study is required prior to its application in humans for this indication.

[edit] 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.

[edit] See also

[edit] References

^ Merck Index, 11th Edition, 4883.
^ S. M. N. Furse (2006). The Chemical and Bio-physical properties of Phosphatidylinositol phosphates, Thesis for M.Res.. Imperial College London.
^ (2003) "Modulation of ATP-dependent chromatin-remodeling complexes by inositol polyphosphates". Science 299 (5603): 112-4. PMID 12434013.
^ (2003) "Regulation of chromatin remodelling by inositol polyphosphates". Science 299 (5603): 114-6. PMID 12434012.
^ Palatnik A, Frolov K, Fux M, Benjamin J (2001). "Double-blind, controlled, crossover trial of inositol versus fluvoxamine for the treatment of panic disorder". Journal of Clinical Psychopharmacology 21 (3): 335–339. PMID 11386498.
^ Fux M, Levine J, Aviv A, Belmaker RH (1996). "Inositol treatment of obsessive-compulsive disorder". American Journal of Psychiatry 153 (9): 1219–21. PMID 8780431.
^ Di Paolo G, De Camilli P (2006). "Phosphoinositides in cell regulation and membrane dynamics". Nature 443 (7112): 651-7. PMID 17035995.
^ Silver SM, Schroeder BM, Sterns RH, Rojiani AM (2006). "Myoinositol administration improves survival and reduces myelinolysis after rapid correction of chronic hyponatremia in rats". J Neuropathol Exp Neurol 65 (1): 37-44. PMID 16410747.