Pyridoxine hydrochloride

Nutrition supplements

Chemical Properties

White or almost white, crystalline powder.

Uses

Pyridoxine Hydrochloride is an acid form of vitamin b6, a water- soluble vitamin. it is soluble in water, and slightly soluble in alco- hol. it is slowly affected by sunlight and is reasonably stable in air. it has a ph of 2.3–3.5. it is also termed vitamin b6 hydrochloride. see pyridoxine.

Definition

ChEBI: Pyridoxine hydrochloride is the hydrochloride salt of pyridoxine. It is a hydrochloride and a vitamin B6. It contains a pyridoxine.

Application

Pyridoxine hydrochloride has been used:
As a vitamin component in a chemically defined diet with balanced metal content for metal depletion studies;
As a component of chemically defined medium (CDM) to culture Staphylococcus aureus WSPPA;
As analytical reference standards for the determination of analytes in pharmaceutical preparations by chromatography and spectrophotometric techniques;
As a vitamin to study the impact of protein expression and post-translational modifications specifically charge heterogeneity;
As a medicine, it is used to prevent or treat certain neurological disorders (peripheral neuropathy) caused by certain drugs (e.g. isoniazid). It is also used in the treatment of certain hereditary disorders (e.g. flavoururic aciduria, hyperoxaluria, homocystinuria).

brand name

Hexa-Betalin (Lilly).

General Description

Vitamin B6 has six forms namely, pyridoxal, pyridoxine, pyridoxamine, pyridoxamine 5′-phosphate, pyridoxine 5′-phosphate and pyridoxal 5′-phosphate. Pyridoxine hydrochloride primarily treats vitamin B6 deficiency and helps alleviate nausea and vomiting during pregnancy. It exists in various forms, including pyridoxine, pyridoxal, and pyridoxamine, which convert into the active coenzyme pyridoxal 5-phosphate (PLP or P5P) in the body.

Biochem/physiol Actions

Vitamin B6 is an essential coenzyme for amino acid, carbohydrate and lipid metabolism. Pyridoxine serves as a primary source in multivitamins. Pyridoxine deficiency is associated with peripheral neuropathy.

Clinical Use

Vitamin B6

Side effects

Common side effects of Pyridoxine hydrochloride include: headache, nausea, drowsiness, mild numbness or tingling. Serious allergic reactions are rare and include: rash, itching/swelling (especially of the face/tongue/throat), severe dizziness, difficulty breathing, decreased sensation of touch, temperature, and vibration; loss of balance or coordination. If serious side effects occur please seek medical attention.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, intramuscular, and subcutaneous routes. Human reproductive effects by ingestion and intramuscular routes: postpartum changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Synthesis

L-alanine, excess oxalic acid and ethanol were subjected to simultaneous ethylation and oxalylation in benzene to produce ethyl N-ethoxyoxalyl-L-alanine, which was then subjected to cyclization, hydrolysis and decarboxylation to produce 4-methyl-5-ethoxyoxazole, which was in turn salted with diethyl maleate by Diels-Alder addition, arylation, and reduction to obtain pyridoxal hydrochloride in a total yield of 56%.

Metabolism

Pyridoxine hydrochloride is metabolised to its active form pyridoxamine phosphate. It is stored mainly in the liver where there is oxidation to 4-pyridoxic acid and other inactive metabolites which are excreted in the urine.

Purification Methods

Purify the vitamin by recrystallisation from EtOH/Me2CO, n-BuOH or MeOH/Et2O. Its solubility in H2O is 22%, and in EtOH it is 1.1%. It is insoluble in Et2O and CHCl3. Acidic aqueous solutions are stable at 120o/30minute. The free base has m 159-160o after recrystallisation from Me2CO and sublimation at 140-145o/0.0001mm. It has UV max at 290nm ( 84,000), 253 and 325nm ( 3,700 and 7,100) in 0.1N aqueous HCl. [Khua & Wendt Chem Ber 71 780 1938, 72 311 1939, Harris & Folkers J Am Chem Soc 61 1242 1939, Harris et al. J Am Chem Soc 62 3198 1940, Beilstein 21/5 V 492.]