65-23-6 Usage
Description
Pyridoxine hydrochloride provides pyridoxine, which is also known as vitamin B6. Vitamin B6 is naturally found in foods such as cereals, beans, vegetables, liver, meat, and eggs.? Vitamin B6 functionalizes as a coenzyme in the metabolism of protein, carbohydrate, and fat. Vitamin 6 is needed to maintain the health of nerves, skin, and red blood cells.
Pyridoxine is used to prevent or treat vitamin B6 deficiency caused by inadequate dietary intake. It is also used to treat drug induced deficiency in patients taking isoniazid or oral contraceptives.
Pharmacodynamics
Vitamin B6 (pyridoxine) is a water-soluble vitamin used in the prophylaxis and treatment of vitamin B6 deficiency and peripheral neuropathy in those receiving isoniazid (isonicotinic acid hydrazide, INH). Vitamin B6 has been found to lower systolic and diastolic blood pressure in a small group of subjects with essential hypertension. Hypertension is another risk factor for atherosclerosis and coronary heart disease. Another study showed pyridoxine hydrochloride to inhibit ADP- or epinephrine-induced platelet aggregation and to lower total cholesterol levels and increase HDL-cholesterol levels, again in a small group of subjects. Vitamin B6, in the form of pyridoxal 5'-phosphate, was found to protect vascular endothelial cells in culture from injury by activated platelets. Endothelial injury and dysfunction are critical initiating events in the pathogenesis of atherosclerosis.
Toxicity
Oral Rat LD50 = 4 gm/kg. Toxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
References
[1] http://www.webmd.com
[2] https://dailymed.nlm.nih.gov
Chemical Properties
crystalline solid
Physical properties
It is one kind of B vitamins, containing pyridoxine or pyridoxal or pyridoxamine.
Appearance: colorless crystals at room temperature. Solubility: soluble in water and
ethanol. Stability: stable in acid liquor but easily destroyed in alkali liquor. Pyridoxol
is resistant to high temperature, but pyridoxal and pyridoxamine are not.
History
The discovery of vitamin was tortuous and legendary. After fat-soluble A and water soluble B were discovered by the year of 1915, the discovery of vitamins entered
into a rapid developed period. In separation process of riboflavin by Kuhn and his
colleagues, they noticed the unusual relationship between growth-promoting activ ity and fluorescence of extracts. Then they supposed that the existence of no fluorescent substances were very necessary for growth-promoting activity of
riboflavin. And they considered this phenomenon as the evidence of a second chem ical existence in the thermostable complex. At last, they named this substance as
vitamin B6 .Vitamin B6 is widely distributed in foods, including meats, whole-grain products
(especially wheat), vegetables, and nuts. In the cereal grains, vitamin B6 is concen trated primarily in the germ and aleuronic layer. Thus, the refining of grains in the
production of flours, which removes much of these fractions, results in substantial
reductions of vitamin B6 content. The chemical forms of vitamin B6 tend to vary
among foods between plant and animal origin: plant tissues contain most pyridox ine (the free alcohol form, pyridoxol), whereas animal tissues contain most pyri doxal and pyridoxamine.
Uses
Different sources of media describe the Uses of 65-23-6 differently. You can refer to the following data:
1. antibacterial
2. pyridoxine HCL is a skin-conditioning agent that is also widely used in hair products.
3. Vitamin B6, a water-soluble vitamin with a solubility of 1 g in 5 ml of water. It functions in the utilization of protein and is an essential nutrient in enzyme reactions. It is necessary for proper growth. During processing, there is a loss due to leaching of the vitamin in water. It is destroyed by high temperatures, high irradiation, and exposure to light. During storage, loss increases with temperature and storage time. It is found in liver, eggs, and meats.
Definition
ChEBI: A hydroxymethylpyridine with hydroxymethyl groups at positions 4 and 5, a hydroxy group at position 3 and a methyl group at position 2. The 4-methanol form of vitamin B6, it is converted intoto pyridoxal phosphate which is a coenzyme f
r synthesis of amino acids, neurotransmitters, sphingolipids and aminolevulinic acid.
Indications
Vitamin B6 deficiency
World Health Organization (WHO)
Pyridoxine (vitamin B6) is listed in theWHO Model List of
Essential Drugs.
General Description
The discovery of vitamin B6 is generally ascribed to Paul Gy?rgy who first realized there was a vitamin that was distinctly different from vitamin B2 in 1934. Pyridoxine (PN) is the C4 hydroxymethyl derivative, pyridoxal (PL) is the C4 formyl derivative and pyridoxamine (PM) is the C4 aminomethyl derivative of 5-(hydroxymethyl)- 2-methylpyridin-3-ol). Each of these are also converted to their corresponding 5'-phosphate derivatives referred to as pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP), and pyridoxamine 5'-phosphate (PMP), respectively . Because of their ability to interconvert, all are considered active forms of vitamin B6 in vivo. Although PLP is the major coenzyme form, PMP can also function as a coenzyme primarily in aminotransferases. The major metabolite is 4-pyridoxic acid, which is excreted in the urine.
Biological Activity
pyridoxine (pyridoxol, vitamin b6, gravidox), also known as vitamin b6, is a form of vitamin b6 found commonly in food and used as dietary supplement. pyridoxine exerts antioxidant effects in cell model of alzheimer's disease via the nrf-2/ho-1 pathway.
Biochem/physiol Actions
Pyridoxine plays a key role in cell maintenance and amino acid metabolism. Deficiency of vitamin B6 leads to anemia especially in pregnant women and seizures in newborns. It serves as cofactor for heme biosynthesis during δ-amino levulinic acid formation, γ-aminobutyric acid (GABA) transaminase and glutamic acid decarboxylase. Vitamin B6 also helps in reactive oxygen species (ROS) scavenging and helps plants in overcoming the abiotic and biotic stress.
Pharmacology
The metabolically active form of vitamin B6 is pyridoxal phosphate, which serves as
a coenzyme of numerous enzymes, most of which are involved in the metabolism of
amino acids. Vitamin B6 functions through the following general mechanisms:
decarboxylation, transamination, racemization, elimination, replacement reactions,
and β-group interconversions.Pyridoxal phosphate is practically involved in all amino acid metabolism reac tions, such as transaminations, transsulfuration, and selenoamino acid metabolism,
in both their biosynthesis and their catabolism. Vitamin B6 also plays an important
role in the tryptophan–niacin conversion, histamine synthesis, neurotransmitter syn thesis, and hemoglobin synthesis.Vitamin B6 has two roles in gluconeogenesis, transaminations and glycogen uti lization. It is required for the utilization of glycogen to release glucose by serving as
a coenzyme of glycogen phosphorylase.
Clinical Use
Pyridoxine is indicated in the treatment and prevention of known or suspected vitamin B6 deficiency, which is most likely to occur in the setting of alcoholism in developed countries. At least seven genetic disorders that result in a vitamin B6 deficiency syndrome in the presence of an adequate dietary intake have been identified. These result from defects in enzymes that are responsible for the bioactivation or utilization of vitamin B6.
Safety Profile
Moderately toxic by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic
effects: ataxia, local anesthetic, paresthesia. When heated to decomposition it emits toxic fumes of Nox
Veterinary Drugs and Treatments
Pyridoxine use in veterinary medicine is relatively infrequent. It
may be of benefit in the treatment of isoniazid (INH) or crimidine
(an older rodenticide) toxicity. Pyridoxine deficiency is apparently
extremely rare in dogs or cats able to ingest food. Cats with severe
intestinal disease may have a greater requirement for pyridoxine in
their diet. Experimentally, pyridoxine has been successfully used
in dogs to reduce the cutaneous toxicity associated with doxorubicin
containing pegylated liposomes (Doxil?). Pyridoxine has been
demonstrated to suppress the growth of feline mammary tumors
(cell line FRM) in vitro.
In humans, labeled uses for pyridoxine include pyridoxine deficiency
and intractable neonatal seizures secondary to pyridoxine
dependency syndrome. Unlabeled uses include premenstrual syndrome
(PMS), carpal tunnel syndrome, tardive dyskinesia secondary
to antipsychotic drugs, nausea and vomiting in pregnancy, hyperoxaluria
type 1 and oxalate kidney stones, and for the treatment
of isoniazid (INH), cycloserine, hydrazine or Gyometra mushroom
poisonings.
Check Digit Verification of cas no
The CAS Registry Mumber 65-23-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 65-23:
(4*6)+(3*5)+(2*2)+(1*3)=46
46 % 10 = 6
So 65-23-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
65-23-6Relevant articles and documents
Pyridoxamine, a scavenger agent of carbohydrates
Adrover, Miquel,Vilanova, Bartolome,Munoz, Francisco,Donoso, Josefa
, p. 154 - 167 (2007)
Pyridoxamine has been found to inhibit protein glycation and to avoid the formation of advanced glycation end-products (AGEs). One of the mechanisms by which pyridoxamine can inhibit glycation involves the scavenger of carbonyl groups with glycation capacity. In this work, we conducted a kinetic study of the reactions of pyridoxamine with various carbohydrates under physiological pH and temperature. The reactions involving hexoses were found to give a tricyclic compound (5) in addition to pyridoxal and pyridoxine. Such a tricyclic compound inhibits the Amadori rearrangement and the formation of other carbonyl compounds with glycating properties. The reactions involving pentoses gave compound 7 and pyridoxal - by transamination of the Schiff base. The transamination reaction enhances the inhibitory action of pyridoxamine. The formation rate constants for the Schiff base, k3, were found to be similar to those for the reactions of D-glucose with amino acids, which suggests competition between pyridoxamine and terminal amino residues in proteins for glycating sites in sugars. These constants are dependent on the electrophilic character of the carbonyl carbon in the carbohydrate.
Biosynthesis of vitamin B6 in Rhizobium: in vitro synthesis of pyridoxine from 1-deoxy-D-xylulose and 4-hydroxy-L-threonine.
Tazoe, Masaaki,Ichikawa, Keiko,Hoshino, Tatsuo
, p. 934 - 936 (2002)
Pyridoxine (vitamin B6) in Rhizobium is synthesized from 1-deoxy-D-xylulose and 4-hydroxy-L-threonine. To define the pathway enzymatically, we established an enzyme reaction system with a crude enzyme solution of R. meliloti IFO14782. The enzyme reaction system required NAD+, NADP+, and ATP as coenzymes, and differed from the E. coli enzyme reaction system comprising PdxA and PdxJ proteins, which requires only NAD+ for formation of pyridoxine 5'-phosphate from 1-deoxy-D-xylulose 5-phosphate and 4-(phosphohydroxy)-L-threonine.
Preparation method of high content vitamin B6
-
Paragraph 0043-0044; 0051-0052, (2019/07/16)
The invention relates to a preparation method of a high content vitamin B6. According to the method, 1,5-dihydro-3,3-disubstituent group-8-methyl-9-alkyl carbonyl oxypyrido [3,4-e]-1,3-dioxane is prepared by the Diels-Alder addition reaction, aromatization reaction and esterification reaction of 4-methyl-5-alkoxyl-oxazole and 2,2-disubstituent group-4,7-dihydro-1,3-dioxepine in the presence of ananhydride through the "one-pot method", and then vitamin B6 is prepared by deprotection. According to the method, the stability of the raw materials of 4-methyl-5-alkoxyl-oxazole and 2,2-disubstituentgroup-4,7-dihydro-1,3-dioxepine are ensured, the reaction is thorough, and the selectivity is high, so that the method provides guarantees for the preparation of high content medicinal vitamin B6.
Effect of structure of nucleophile and substrate on the quaternization of heterocyclic amines
Zhuravlev,Verolainen,Voronchikhina
experimental part, p. 1025 - 1028 (2011/01/11)
The influence of the nature of the quaternizing agent and substrate on the quaternization of heterocyclic amines, derivatives of pyridine, ss-picoline, nicotinamide, pyridoxine, was studied. The synthesized compounds were characterized by IR spectroscopy and elemental analysis. The conclusions were made about the effect of the structure of nucleophile and substrate on the process of quaternization reaction. Pleiades Publishing, Ltd., 2010.
Xi:Irritant;
