Pyridoxine (CHEM002133)

Record Information
Version1.0
Creation Date2009-07-21 20:26:12 UTC
Update Date2026-05-14 16:24:23 UTC
Accession NumberCHEM002133
Identification
Common NamePyridoxine
ClassSmall Molecule
Description
Pyridoxine is the 4-methanol form of vitamin B6 and is converted to pyridoxal 5-phosphate in the body. Pyridoxal 5-phosphate is a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. Although pyridoxine and vitamin B6 are still frequently used as synonyms, especially by medical researchers, this practice is erroneous and sometimes misleading. Pyridoxine is one of the compounds that can be called vitamin B6. Pyridoxine assists in the balancing of sodium and potassium as well as promoting red blood cell production. It is linked to cancer immunity and helps fight the formation of homocysteine. It has been suggested that Pyridoxine might help children with learning difficulties, and may also prevent dandruff, eczema, and psoriasis. In addition, pyridoxine can help balance hormonal changes in women and aid in immune system. Lack of pyridoxine may cause anemia, nerve damage, seizures, skin problems, and sores in the mouth. Deficiency, though rare because of widespread distribution in foods, leads to the development of peripheral neuritis in adults and affects the central nervous system in children.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Inflammatory Agent
  • Drug
  • Essential Vitamin
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Vitamin
  • Vitamin B Complex
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridineChEBI
3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridineChEBI
3-Hydroxy-4,5-dimethylol-alpha-picolineChEBI
5-Hydroxy-6-methyl-3,4-pyridinedimethanolChEBI
PyridoxolChEBI
Vitamin b6ChEBI
3-Hydroxy-4,5-dimethylol-a-picolineGenerator
3-Hydroxy-4,5-dimethylol-α-picolineGenerator
2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridineHMDB
2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridineHMDB
2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridineHMDB
3-Hydroxy-2-picoline-4,5-dimethanolHMDB
AdermineHMDB
GravidoxHMDB
HydoxinHMDB
PiridossinaHMDB
PiridoxinaHMDB
PyridoxinHMDB
PyridoxinumHMDB
PyridoxolumHMDB
Pyridoxol hydrochlorideHMDB
RodexHMDB
Pyridoxine hydrochlorideHMDB
Chemical FormulaC8H11NO3
Average Molecular Mass169.178 g/mol
Monoisotopic Mass169.074 g/mol
CAS Registry Number65-23-6
IUPAC Name4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol
Traditional Namepyridoxine
SMILESCC1=C(O)C(CO)=C(CO)C=N1
InChI IdentifierInChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3
InChI KeyLXNHXLLTXMVWPM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridoxines
Direct ParentPyridoxines
Alternative Parents
Substituents
  • Pyridoxine
  • Methylpyridine
  • Hydroxypyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Erythrocyte
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Vitamin B6 MetabolismSMP00017 map00750
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point159-162°C
Boiling PointNot Available
Solubility2.2E+005 mg/L
Predicted Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-0.57ALOGPS
logP-0.95ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)5.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.58 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.11 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral; parenteral (intramuscular). The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Pyridoxine is absorbed mainly in the jejunum.
Mechanism of ToxicityVitamin B6 is the collective term for a group of three related compounds, pyridoxine (PN), pyridoxal (PL) and pyridoxamine (PM), and their phosphorylated derivatives, pyridoxine 5'-phosphate (PNP), pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP). Although all six of these compounds should technically be referred to as vitamin B6, the term vitamin B6 is commonly used interchangeably with just one of them, pyridoxine. Vitamin B6, principally in its biologically active coenzyme form pyridoxal 5'-phosphate, is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemogloblin, sphingomyelin and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA).
MetabolismHepatic. Half Life: 15-20 days
Toxicity ValuesLD50: 4 gm/kg (oral, rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of vitamin B6 deficiency and for the prophylaxis of isoniazid-induced peripheral neuropathy.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsToxic effects include convulsions, dyspnea, hypermotility, diarrhea, ataxia and muscle weakness.
TreatmentAdminister charcoal as a slurry. (17)
Concentrations
Not Available
External Links
DrugBank IDDB00165
HMDB IDHMDB0000239
FooDB IDFDB000574
Phenol Explorer IDNot Available
KNApSAcK IDC00001551
BiGG IDNot Available
BioCyc IDPYRIDOXINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPyridoxine
Chemspider ID1025
ChEBI ID16709
PubChem Compound ID1054
Kegg Compound IDC00314
YMDB IDYMDB00037
ECMDB IDECMDB00239
References
Synthesis Reference

Harumi Kita, “Production of pyridoxine.” U.S. Patent US4339586, issued October, 1972.

MSDSLink
General References
1. Itov, Z. I.; Stepanova, S. V.; El'yanov, B. S.; Gunar, V. I. Synthesis of pyridoxine under high pressure. Khimiko-Farmatsevticheskii Zhurnal (1987), 21(7), 858-62.
2. Henderson JM, Codner MA, Hollins B, Kutner MH, Merrill AH: The fasting B6 vitamer profile and response to a pyridoxine load in normal and cirrhotic subjects. Hepatology. 1986 May-Jun;6(3):464-71.
3. Chiang EP, Selhub J, Bagley PJ, Dallal G, Roubenoff R: Pyridoxine supplementation corrects vitamin B6 deficiency but does not improve inflammation in patients with rheumatoid arthritis. Arthritis Res Ther. 2005;7(6):R1404-11. Epub 2005 Oct 14.
4. Manyam BV, Ferraro TN, Hare TA: Isoniazid-induced alteration of CSF neurotransmitter amino acids in Huntington's disease. Brain Res. 1987 Apr 7;408(1-2):125-30.
5. Temesvari P, Szilagyi I, Eck E, Boda D: Effects of an antenatal load of pyridoxine (vitamin B6) on the blood oxygen affinity and prolactin levels in newborn infants and their mothers. Acta Paediatr Scand. 1983 Jul;72(4):525-9.
6. McCully KS: Homocysteine, vitamins, and prevention of vascular disease. Mil Med. 2004 Apr;169(4):325-9.
7. Chen S, Ito M, Saijo T, Naito E, Kuroda Y: Molecular genetic analysis of pyridoxine-nonresponsive homocystinuric siblings with different blood methionine levels during the neonatal period. J Med Invest. 1999 Aug;46(3-4):186-91.
8. Wasilewska A, Narkiewicz M, Rutkowski B, Lysiak-Szydlowska W: Is there any relationship between lipids and vitamin B levels in persons with elevated risk of atherosclerosis? Med Sci Monit. 2003 Mar;9(3):CR147-51.
9. Kidd GS, Dimond R, Kark JA, Whorton N, Vigersky RA: The effects of pyridoxine on pituitary hormone secretion in amenorrhea-galactorrhea syndromes. J Clin Endocrinol Metab. 1982 Apr;54(4):872-5.
10. Plecko B, Stockler-Ipsiroglu S, Paschke E, Erwa W, Struys EA, Jakobs C: Pipecolic acid elevation in plasma and cerebrospinal fluid of two patients with pyridoxine-dependent epilepsy. Ann Neurol. 2000 Jul;48(1):121-5.
11. Pirulli D, Marangella M, Amoroso A: Primary hyperoxaluria: genotype-phenotype correlation. J Nephrol. 2003 Mar-Apr;16(2):297-309.
12. Amoroso A, Pirulli D, Florian F, Puzzer D, Boniotto M, Crovella S, Zezlina S, Spano A, Mazzola G, Savoldi S, Ferrettini C, Berutti S, Petrarulo M, Marangella M: AGXT gene mutations and their influence on clinical heterogeneity of type 1 primary hyperoxaluria. J Am Soc Nephrol. 2001 Oct;12(10):2072-9.
13. Tolis G, Laliberte R, Guyda H, Naftolin F: Ineffectiveness of pyridoxine (B6) to alter secretion of growth hormone and prolactin and absence of therapeutic effects on galactorrhea-amenorrhea syndromes. J Clin Endocrinol Metab. 1977 Jun;44(6):1197-9.
14. Esteve-Romero J, Capella-Peiro ME, Monferrer-Pons L, Gil-Agusti M: Micellar liquid chromatography in clinical chemistry: application to the monitorization of B6 vitamins. Clin Chim Acta. 2004 Oct;348(1-2):69-77.
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24035968
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2580028