4-Deoxypyridoxine

4-Deoxypyridoxine
Names
	Preferred IUPAC name 5-(Hydroxymethyl)-2,4-dimethylpyridin-3-ol
Identifiers
CAS Number	148-51-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	5869 ;
PubChem CID	6094;
UNII	P9QAN95HHX ;
CompTox Dashboard (EPA)	DTXSID50209849 ;
	InChI InChI=1S/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3 Key: KKOWAYISKWGDBG-UHFFFAOYSA-N ; InChI=1/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3 Key: KKOWAYISKWGDBG-UHFFFAOYAH;
	SMILES CC1=C(C(=NC=C1CO)C)O; Oc1c(c(cnc1C)CO)C;
Properties
Chemical formula	C8H11NO2
Molar mass	153.181 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	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] 4-Deoxypyridoxine has also been described as an inhibitor of sphingosine-1-phosphate lyase.^[5]

References[]

^ 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. doi:10.1093/jn/111.2.391. PMID 6257871.
^ 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. doi:10.1042/bj2100633. PMC 1154271. PMID 6135414.
^ 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.
^ 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. S2CID 23457740.
^ Weigel, Cynthia; Hüttner, Sören S.; Ludwig, Kristin; Krieg, Nadine; Hofmann, Susann; Schröder, Nathalie H.; Robbe, Linda; Kluge, Stefan; Nierhaus, Axel; Winkler, Martin S.; Rubio, Ignacio (2020-08-01). "S1P lyase inhibition protects against sepsis by promoting disease tolerance via the S1P/S1PR3 axis". EBioMedicine. 58. doi:10.1016/j.ebiom.2020.102898. ISSN 2352-3964. PMID 32711251.

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[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. doi:10.1093/jn/111.2.391. 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. doi:10.1042/bj2100633. PMC 1154271. PMID 6135414.

[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. S2CID 23457740.

[5] Weigel, Cynthia; Hüttner, Sören S.; Ludwig, Kristin; Krieg, Nadine; Hofmann, Susann; Schröder, Nathalie H.; Robbe, Linda; Kluge, Stefan; Nierhaus, Axel; Winkler, Martin S.; Rubio, Ignacio (2020-08-01). "S1P lyase inhibition protects against sepsis by promoting disease tolerance via the S1P/S1PR3 axis". EBioMedicine. 58. doi:10.1016/j.ebiom.2020.102898. ISSN 2352-3964. PMID 32711251.

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