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CAS NUMBER: 6164-87-0
MOLECULAR FORMULA: C10H13NO7
MOLECULAR WEIGHT: 259.21
Nicotinyl alcohol is a Nicotinyl alcohol derivative used as a hypolipidemic agent and as a vasodilator.
Nicotinyl alcohol causes flushing and may decrease blood pressure.
Nicotinyl alcohol appears as a crystal that dissolves in water and alcohol with ease, also soluble in ether; melting range 147–148 ºC.
Nicotinyl alcohol is a brief peripheral vasodilator; this compound was made to make its action longer and effective.
Nicotinyl alcohol provokes cutaneous flushing in head and upper thorax with heat, but with no major effects in blood pressure.
Nicotinyl alcohol is used in peripheral vascular diseases, like arteriosclerosis obliterans, Raynaud's disease, thromboangiitis obliterans, arterial embolism, chilblains or migraine associated with vascular spasm.
Fischer and Tebrock worked with this drug in more than two hundred patients for more than three years, achieving effective improvements, mainly in symptoms related to intermittent claudication, ulcer healing and others.
Nicotinyl alcohol tartrate is a member of pyridines and a tartrate salt.
Alcohol analog of Nicotinyl alcohol which is a direct-acting peripheral vasodilator that causes flushing and may decrease blood pressure.
Nicotinyl alcohol belongs to the class of organic compounds known as pyridines and derivatives.
These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Nicotinyl alcohol can be analyzed by this reverse phase (RP) HPLC method with simple conditions.
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid.
Smaller 3 µm particles columns available for fast UPLC applications.
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation.
Nicotinyl alcohol also suitable for pharmacokinetics.
Nicotinyl alcohol is a Nicotinyl alcohol derivative used as a hypolipidemic agent and as a vasodilator.
Nicotinyl alcohol causes flushing and may decrease blood pressure.
Nicotinyl alcohol, 3-pyridinecarboxylicacid (Nicotinyl alcohol), is effective in the treatment of all types ofhyperlipoproteinemia except type I, at doses above thosegiven as a vitamin supplement.
The drug reduces VLDLsynthesis and, subsequently, its plasma products, IDL andLDL.
Plasma triglyceride levels are reduced because of thedecreased VLDL production.
Although Nicotinyl alcohol is the drug of choicefor type II hyperlipoproteinemias, its use is limited becauseof the vasodilating side effects.
Flushing occurs inpractically all patients but generally subsides when thedrug is discontinued.
The hypolipidemic effects of Nicotinyl alcohol may be caused byits ability to inhibit lipolysis (i.e., prevent the release ofFFAs and glycerol from fatty tissues).
Therefore, there is areduced reserve of FFA in the liver and diminution oflipoprotein biosynthesis, which reduces the production ofVLDL.
The decreased formation of lipoproteins leads to apool of unused cholesterol normally incorporated inVLDL.
This excess cholesterol is then excreted throughthe biliary tract.
USES OF NICOTINYL ALCOHOL:
Nicotinyl alcohol can be used as antineoplastic and used in the synthesis of histone deacetylase inhibitors.
Nicotinyl alcohol is an important factor in delivering hydrogen and fighting pellagra in organisms; it helps maintain skin and nerve health and stimulate digestion.
Nicotinyl alcohol or Nicotinyl alcoholamide are used to treat and prevent pellagra.
This is a disease caused by Nicotinyl alcohol deficiency.
Nicotinyl alcohol is also used to treat high cholesterol.
In some cases, Nicotinyl alcohol taken with colestipol can work as well as colestipol and a statin medicine.
Nicotinyl alcohol USP granular is used for food fortification, as dietary supplement and as an intermediate of pharmaceuticals.
Nicotinyl alcohol feed grade is used as vitamin for poultry, swines, ruminants, fish, dogs and cats, etc.
Nicotinyl alcohol is also used as intermediate for Nicotinyl alcohol derivatives and technical applications.
Nicotinyl alcohol is also known as vitamin B3.
Nicotinyl alcohol is a water-soluble conditioning agent that improves rough, dry, or flaky skin, helping smooth the skin and improve its suppleness.
Nicotinyl alcohol enhances the appearance and feel of hair, by increasing body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment. When used in the formulation of skin care products, Nicotinyl alcoholamide and Nicotinyl alcohol enhance the appearance of dry or damaged skin by reducing flaking and restoring suppleness.
Nicotinyl alcohol.
Nicotinyl alcohol is a precursor of the coenzymes NAD and NADP.
Widely distributed in nature; appreciable amounts are found in liver , fish, yeast and cereal grains. Dietary deficiency is associated with pellagra.
The term "Nicotinyl alcohol" has also been applied.
Nicotinyl alcohol is a water-soluble b-complex vitamin that is necessary for the growth and health of tissues.
Nicotinyl alcohol prevents pellagra.
Nicotinyl alcohol has a solubility of 1 g in 60 ml of water and is readily soluble in boiling water.
Nicotinyl alcohol is relatively stable in storage and no loss occurs in ordinary cooking. Sources include liver, peas, and fish.
Nicotinyl alcohol was originally termed Nicotinyl alcohol and also functions as a nutrient and dietary supplement.
Nicotinyl alcohol has been esterified to prolong itshypolipidemic effect.
Nicotinyl alcohol has been more effective experimentally than Nicotinyl alcohol in reducingcholesterol levels in rabbits.
Nicotinyl alcohols have been used in the treatment ofpatients with atherosclerosis obliterans.
The usual maintenance dose of Nicotinyl alcohol is 3 to 6 g/daygiven in three divided doses.
Nicotinyl alcohol is usually given atmealtimes to reduce the gastric irritation that often accompanieslarge doses.
-Used to solubilize riboflavin and as a peripheral vasodilator
-Alcohol analog of Nicotinyl alcohol
-A direct-acting peripheral vasodilator that is used in vasospasm and threatened gangrene
PHYSICAL AND CHEMICAL PROPERTIES OF NICOTINYL ALCOHOL:
-Melting point: -7 °C
-Boiling point: 154 °C/28 mmHg (lit.)
-density: 1.124 g/mL at 25 °C (lit.)
-refractive index: n20/D 1.545(lit.)
-Fp: >230 °F
-solubility: 1000mg/l
-pka: 13.68±0.10(Predicted)
-form: liquid (clear)
-color: clear light yellow
-PH: 7-8 (100g/l, H2O, 20℃)
-Water Solubility: soluble
-Sensitive: Hygroscopic
-Merck: 14,6527
-BRN: 107851
-InChIKey: MVQVNTPHUGQQHK-UHFFFAOYSA-N
-CAS DataBase Reference: 100-55-0(CAS DataBase Reference)
-NIST Chemistry Reference: Nicotinyl Alcohol(100-55-0)
-EPA Substance Registry System: 3-Pyridinemethanol (100-55-0)
CHEMICAL PROPERTIES OF NICOTINYL ALCOHOL:
Nicotinyl alcohol, also known as Nicotinyl alcohol or vitamin B3, is a white crystal or crystalline powder, odorless or has a slight odor, slight sour taste.
Melting point is 234-237℃.
Easily soluble in hot water, hot ethanol, alkaline water, propylene glycol, and chloroform.
Slightly soluble in water and ethanol; 100ml room temperature water can dissolve 1.6g.
Insoluble in ether and ester solutions.
The PH of 1% aqueous solution is 3.0-4.0.
Stable in heat, acidity and alkalinity.
Nicotinyl alcohol can produce a variety of adverse effects, depending on the intake and health of the consumer.
The skin flushing reaction produced by Nicotinyl alcohol has been recognized for more than 70 years (Bean 1978).
When taken on an empty stomach, crystalline Nicotinyl alcohol in doses as small as 10 mg may produce a mild and transient, but noticeable, flushing reaction.
While not desirable, such reactions produce no known adverse consequences, and they are almost never perceptible when small amounts of Nicotinyl alcohol are taken in tablet or capsule form or consumed as part of food.
Nicotinyl alcohol is sometimes referred to as Nicotinyl alcohol or nicotinamide and earlier called the P-P factor, antipellagra factor, antiblacktongue factor, and vitamin B4, Nicotinyl alcohol is available in several forms (Nicotinyl alcohol, Nicotinyl alcoholamide, Nicotinyl alcoholamide ascorbate, etc.) for use as a nutrient and dietary supplement.
Nicotinyl alcohol is frequently identified with the B complex vitamin grouping.
Early in the research on Nicotinyl alcohol, a nutritional Nicotinyl alcohol deficiency was identified as the cause of pellagra in humans, blacktongue in dogs, and certain forms of dermatosis in humans.
Nicotinyl alcohol deficiency is also associated with perosis in chickens as well as poor feathering of the birds.
PHYSCIAL PROPERTIES OF NICOTINYL ALCOHOL:
Nicotinyl alcohol and nicotinamide are colorless crystalline substances.
Each is insol uble or only sparingly soluble in organic solvents.
Nicotinyl alcohol is slightly soluble in water and ethanol; nicotinamide is very soluble in water and moderately soluble in ethanol
Nicotinyl alcohol is amphoteric and forms salts with acids as well as bases.
Nicotinyl alcohols car boxyl group can form esters and anhydrides and can be reduced.
Both Nicotinyl alcohol and nicotinamide are very stable in dry form, but in solution nicotinamide is hydro lyzed by acids and bases to yield nicotinic ac
The coenzyme forms of Nicotinyl alcohol are the pyridine nucleotides, NAD(H) and NADP(H).
In each of these compounds, the electron-withdrawing effect of the N-1 atom and the amide group of the oxidized pyridine nucleus enables the pyridine C-4 atom to react with many nucleophilic agents.
Nicotinyl alcohol is the reaction with hydride ions that is the basis of the enzymatic hydrogen transfer by the pyridine nucleotides; the reaction involves the transfer of two electrons in a single step
Several substituted pyridines are antagonists of Nicotinyl alcohol in biological systems: pyridine-3-sulfonic acid, 3-acetylpyridine, isoNicotinyl alcohol hydrazine, 17 and 6-aminonicotinamide.
MECHANISM OF ACTION OF NICOTINYL ALCOHOL:
Nicotinyl alcohol decreases formation and secretion of VLDL by the liver.
This action appears secondary to its ability to inhibit fatty acid mobilization from adipose tissue.
Circulating free fatty acids provide the main source of fatty acids for hepatic triglyceride synthesis, and lowering triglyceride synthesis lowers VLDL formation and secretion by the liver.
Since plasma VLDL is the source of LDL, lowering VLDL can ultimately lower LDL.
In addition, Nicotinyl alcohol shifts LDL particles to larger (more buoyant) sizes.
The larger LDL particles are thought to be less atherogenic.
Nicotinyl alcohol can also significantly increase plasma HDL levels; the mechanism is unknown.
MANUFACTURING PROCESS OF NICOTINYL ALCOHOL:
Nicotinyl alcohol is prepared by suspending 5 kg of catalyst grade charcoal in 200 liters of water, in a pressure vessel, and adding thereto 25 liters of 4% (as Pd metal) aqueous palladous chloride.
Air is displaced from the vessel and then hydrogen is passed into the aqueous mixture at a pressure of 3 to 5 psi, while stirring, until no further absorption is noted and the chloride is completely reduced to metal.
To the aqueous suspension of the palladized charcoal catalyst thus obtained are added 20.8 kg of 3-cyano-pyridine (96% purity); and then are added 70 liters of a hydrochloric acid solution prepared by diluting 30 liters of 36% HCl with 40 liters of water.
This represents approximately 1.75 mols of HCl for each mol of 3-cyano-pyridine.
The suspension is maintained at 10° to 15°C and stirred continuously while introducing a current of hydrogen at a pressure of 3 to 5 psi.
When absorption of hydrogen ceases and the 3-cyanopyridine is completely reduced, the reaction mixture is filtered to remove the catalyst.
The filter cake is washed with 40 liters of water in two equal portions, and the wash water is added to the filtrate.
The combined liquors, which comprise an aqueous hydrochloric acid solution of 3-aminomethyl-pyridine hydrochloride, are then heated to a temperature of 60° to 65°C, and ethyl nitrite gas is passed into the heated solution.
The ethyl nitrite is generated by placing 20 liters of 90% ethyl alcohol in a suitable vessel, diluting with 200 liters of water, and, while stirring, adding to the dilute alcohol 18.3 kg of nitrosyl chloride at the rate of 2.25 kg per hour.
When all the ethyl nitrite has been added, the reaction mixture is refluxed for approximately one hour, then concentrated to dryness under reduced pressure (25 to 30 mm Hg) and at a maximum temperature of 70°C.
The crystalline residue is dissolved in 35 liters of water and adjusted to a pH of 8 to 9 by addition (with cooling and stirring) of 11 to 12 kg of caustic soda.
Nicotinyl alcohol formed is filtered off, and the filter cake is washed with 20 liters of normal butyl alcohol.
Nicotinyl alcohol is used for the first extraction of the product from the aqueous filtrate.
The filtrate is then further extracted with four successive 20-liter portions of n-butyl alcohol.
All the extracts are combined and concentrated in vacuo (100°C/20 mm) to remove the n-butyl alcohol.
Nicotinyl alcohol is submitted to fractionation under reduced pressure.
The forerun (up to 112°C/2 to 3 mm) consists of a small amount of n-butyl alcohol and some 3-pyridylcarbinol.
The main fraction, boiling at 112° to 114°C/2 to 3 mm, consists of 3-pyridylcarbinol.
SYNONYM:
Nicotinyl tartrate
6164-87-0
Danaden
Radecol
Niacol
Ronicol retard
UNII-5G605ZIE90
Ronicol tartrate
Roniacol tartrate
Zuganol-R
3-Pyridylmethanol tartrate
Nicotinyl alcohol tartrate [JAN]
Pyridyl-3-carbinol tartrate
3-Pyridylcarbinol bitartrate
5G605ZIE90
Neu-2121
(2R,3R)-2,3-dihydroxybutanedioic acid;pyridin-3-ylmethanol
