4-Deoxypyridoxine

4-Deoxypyridoxine
IUPAC name 5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol
Identifiers
CAS number	148-51-6
PubChem	6094
ChemSpider	5869 Y
Jmol-3D images	Image 1 Image 2
SMILES CC1=C(C(=NC=C1CO)C)O Oc1c(c(cnc1C)CO)C
InChI InChI=1S/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3 Y Key: KKOWAYISKWGDBG-UHFFFAOYSA-N Y InChI=1/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3 Key: KKOWAYISKWGDBG-UHFFFAOYAH
Properties
Molecular formula	C8H11NO2
Molar mass	153.18 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Deoxypyridoxine is a vitamin B₆ antagonist.^[1] It may be toxic to developing embryos since it can have negative effects on collagen and elastin during development.^[2] The presence of this compound can produce vitamin B₆ deficiency, which suppresses the immune system.^[3] This immunosuppression can be beneficial in animal models of Trichinella spiralis infections.^[4]

References

1. ^ Coburn SP, Mahuren JD, Schaltenbrand WE, Wostmann BS, Madsen D (1 February 1981). "Effects of vitamin B-6 deficiency and 4'- deoxypyridoxine on pyridoxal phosphate concentrations, pyridoxine kinase and other aspects of metabolism in the rat". J. Nutr. 111 (2): 391–8. PMID 6257871. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=6257871. 
2. ^ Bird TA, Levene CI (1983). "The effect of a vitamin B-6 antagonist, 4-deoxypyridoxine, on the cross-linking of collagen in the developing chick embryo". Biochem. J. 210 (3): 633–8. PMC 1154271. PMID 6135414. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1154271. 
3. ^ Trakatellis A, Dimitriadou A, Exindari M, et al. (1992). "Effect of pyridoxine deficiency on immunological phenomena". Postgrad Med J 68 Suppl 1: S70–7. PMID 1409221. 
4. ^ Frydas S, Papaioanou N, Vlemmas I, et al. (1999). "Vitamin B₆-deficient diet plus 4-deoxypyridoxine (4-DPD) reduces the inflammatory response induced by T. spiralis in diaphragm, masseter and heart muscle tissue of mice". Mol. Cell. Biochem. 197 (1–2): 79–85. doi:10.1023/A:1006958310081. PMID 10485327.