Inositol nicotinate

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Inositol nicotinate
Inositol nicotinate.png
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
oral
ATC code
Legal status
Legal status
Identifiers
  • cyclohexane-1,2,3,4,5,6-hexayl hexanicotinate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.026.806 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C42H30N6O12
Molar mass 810.732 g·mol−1
3D model (JSmol)
Melting point 255 °C (491 °F)
  • O=C(O[C@H]6[C@H](OC(=O)c1cccnc1)[C@H](OC(=O)c2cccnc2)[C@H](OC(=O)c3cccnc3)[C@@H](OC(=O)c4cccnc4)[C@@H]6OC(=O)c5cccnc5)c7cccnc7

Inositol nicotinate, also called inositol hexanicotinate and inositol hexaniacinate, is marketed in the United States as a "no-flush niacin" dietary supplement. [1] Flushing, in physiology, essentially means that epidermal tissues have become reddened, such as when the skin is irritated from the histamine responses related to an allergic reaction, or from recent physical exercise, or even from anger or embarrassment.

This form of niacin is supposed to reduce or prevent flushing by being broken down into the metabolites niacin (nicotinic acid) and inositol at a slow rate. [1]

See also

Related Research Articles

<span class="mw-page-title-main">Nicotinamide</span> Dietary supplement and medication

Niacinamide or nicotinamide is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used by mouth to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, niacinamide has the benefit of not causing skin flushing. As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. It is a water-soluble vitamin. Niacinamide is the supplement name, while nicotinamide is the scientific name.

<span class="mw-page-title-main">Niacin</span> Organic compound and a form of vitamin B3

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitaminB3, an essential human nutrient. It can be manufactured by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.

A nutrient is a substance used by an organism to survive, grow, and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi, and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures, such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted to smaller molecules in the process of releasing energy, such as for carbohydrates, lipids, proteins, and fermentation products, leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.

<span class="mw-page-title-main">Flushing (physiology)</span> Medical condition

Flushing is to become markedly red in the face and often other areas of the skin, from various physiological conditions. Flushing is generally distinguished from blushing, since blushing is psychosomatic, milder, generally restricted to the face, cheeks or ears, and generally assumed to reflect emotional stress, such as embarrassment, anger, or romantic stimulation. Flushing is also a cardinal symptom of carcinoid syndrome—the syndrome that results from hormones being secreted into systemic circulation.

B vitamins are a class of water-soluble vitamins that play important roles in cell metabolism and synthesis of red blood cells. They are a chemically diverse class of compounds, but are associated in diet, often occurring together in the same foods. Dietary supplements containing all eight are referred to as a vitamin B complex. Individual B vitamins are referred to by B-number or by chemical name, such as B1 for thiamine, B2 for riboflavin, and B3 for niacin, while some are more commonly recognized by name than by number, such as pantothenic acid (B5), biotin (B7), and folate (B9).

<span class="mw-page-title-main">Erythema</span> Symptom defined as redness of the skin or mucous membranes mostly due to inflammation

Erythema is redness of the skin or mucous membranes, caused by hyperemia in superficial capillaries. It occurs with any skin injury, infection, or inflammation. Examples of erythema not associated with pathology include nervous blushes.

<span class="mw-page-title-main">Inositol</span> Carbocyclic sugar

Inositol, primarily the isomer myo-inositol, is a carbocyclic sugar that is abundant in the brain and other mammalian tissues; it mediates cell signal transduction in response to a variety of hormones, neurotransmitters, and growth factors and participates in osmoregulation. Concerning regulation of osmosis, in most mammalian cells the intracellular concentrations of myo-inositol are 5 to 500 times greater than the extracellular concentrations.

<span class="mw-page-title-main">Maculopapular rash</span> Type of rash

A maculopapular rash is a type of rash characterized by a flat, red area on the skin that is covered with small confluent bumps. It may only appear red in lighter-skinned people. The term "maculopapular" is a compound: macules are small, flat discolored spots on the surface of the skin; and papules are small, raised bumps. It is also described as erythematous, or red.

<span class="mw-page-title-main">Carcinoid</span> A slow-growing type of neuroendocrine tumor

A carcinoid is a slow-growing type of neuroendocrine tumor originating in the cells of the neuroendocrine system. In some cases, metastasis may occur. Carcinoid tumors of the midgut are associated with carcinoid syndrome.

Mother is an energy drink that originated in Australia and New Zealand by Coca-Cola. Introduced in late 2006 after Coca-Cola's failed attempt to purchase Red Bull, it competes with the two leading energy drinks on the market, V and Red Bull, in the $151 million industry.

<span class="mw-page-title-main">Emerge Stimulation Drink</span> UK energy drink

Emerge is a carbonated mixed-fruit flavour energy drink from the United Kingdom which contains taurine and caffeine. It is produced by the Cott Corporation at their packaging facility at Kegworth in Leicestershire. It is sold in Sainsburys, Asda, Poundland, Home Bargains and other retailers, usually newsagents. Its primary difference from competing brand-name energy drinks such as Red Bull and Relentless is the comparatively lower RRP of between 59p and 75p. It can often be found at a lower price than this, for example in pound shops or more recently, for loyalty card prices.

<span class="mw-page-title-main">Acipimox</span> Chemical compound

Acipimox is a niacin derivative used as a lipid-lowering agent. It reduces triglyceride levels and increases HDL cholesterol. It may have less marked adverse effects than niacin, although it is unclear whether the recommended dose is as effective as standard doses of niacin.

<span class="mw-page-title-main">Nicotinyl alcohol</span> Chemical compound

Nicotinyl alcohol (pyridylcarbinol) is a niacin derivative used as a hypolipidemic agent and as a vasodilator. It causes flushing and may decrease blood pressure.

<span class="mw-page-title-main">Hydroxycarboxylic acid receptor 2</span> Protein-coding gene in the species Homo sapiens

Hydroxycarboxylic acid receptor 2 (HCA2), also known as GPR109A and niacin receptor 1 (NIACR1), is a protein which in humans is encoded (its formation is directed) by the HCAR2 gene and in rodents by the Hcar2 gene. The human HCAR2 gene is located on the long (i.e., "q") arm of chromosome 12 at position 24.31 (notated as 12q24.31). Like the two other hydroxycarboxylic acid receptors, HCA1 and HCA3, HCA2 is a G protein-coupled receptor (GPCR) located on the surface membrane of cells. HCA2 binds and thereby is activated by D-β-hydroxybutyric acid (hereafter termed β-hydroxybutyric acid), butyric acid, and niacin (also known as nicotinic acid). β-Hydroxybutyric and butyric acids are regarded as the endogenous agents that activate HCA2. Under normal conditions, niacin's blood levels are too low to do so: it is given as a drug in high doses in order to reach levels that activate HCA2.

<span class="mw-page-title-main">Inositol-phosphate phosphatase</span> Class of enzymes

The enzyme Inositol phosphate-phosphatase is of the phosphodiesterase family of enzymes. It is involved in the phosphophatidylinositol signaling pathway, which affects a wide array of cell functions, including but not limited to, cell growth, apoptosis, secretion, and information processing. Inhibition of inositol monophosphatase may be key in the action of lithium in treating bipolar disorder, specifically manic depression.

Vitamins occur in a variety of related forms known as vitamers. A vitamer of a particular vitamin is one of several related compounds that performs the functions of said vitamin and prevents the symptoms of deficiency of said vitamin.

<span class="mw-page-title-main">Laropiprant</span> Chemical compound

Laropiprant (INN) was a drug used in combination with niacin to reduce blood cholesterol that is no longer sold, due to increases in side-effects with no cardiovascular benefit. Laropiprant itself has no cholesterol lowering effect, but it reduces facial flushes induced by niacin.

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Vitamin B<sub>3</sub> Class of chemically related vitamers

Vitamin B3, colloquially referred to as niacin, is a vitamin family that includes three forms, or vitamers: niacin (nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the body to nicotinamide adenine dinucleotide (NAD). NAD is required for human life and people are unable to make it within their bodies without either vitamin B3 or tryptophan. Nicotinamide riboside was identified as a form of vitamin B3 in 2004.

<span class="mw-page-title-main">Menthyl nicotinate</span> Chemical compound

Menthyl nicotinate is an organic compound with the formula C16H23NO2. It is the ester of nicotinic acid (niacin, vitamin B3) and menthol. At room temperature, menthyl nicotinate is a colorless, odorless, viscous liquid.

References

  1. 1 2 Taheri R (15 January 2003). "No-Flush Niacin for the Treatment of Hyperlipidemia". Medscape.com. Retrieved 14 September 2010.