Allithiamine

Allithiamine
Clinical data
ATC code	None;
Identifiers
	IUPAC name N-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-N-[(1Z)-4-hydroxy-1-methyl-2-(prop-2-en-1-yldisulfanyl)but-1-en-1-yl]formamide;
CAS Number	554-44-9 ;
PubChem CID	3037212;
ChemSpider	2301021 ;
UNII	83SWN21920;
Chemical and physical data
Formula	C15H22N4O2S2
Molar mass	354.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=CN(/C(=C(\SSC\C=C)CCO)C)Cc1cnc(nc1N)C;
	InChI InChI=1S/C15H22N4O2S2/c1-4-7-22-23-14(5-6-20)11(2)19(10-21)9-13-8-17-12(3)18-15(13)16/h4,8,10,20H,1,5-7,9H2,2-3H3,(H2,16,17,18)/b14-11- ; Key:WNCAVNGLACHSRZ-KAMYIIQDSA-N ;
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Allithiamine (thiamine allyl disulfide or TAD) is a lipid-soluble form of vitamin B₁ which was discovered in garlic (Allium sativum) in the 1950s along with its homolog prosultiamine.^[1] They were both investigated for their ability to treat Wernicke–Korsakoff syndrome and beriberi better than thiamine.^[2]

References

^ Fujiwara M, Watanabe H, Matsui K (1954). ""Allithiamine" A Newly Found Derivative of Vitamin B1". The Journal of Biochemistry. 41: 29–39. doi:10.1093/oxfordjournals.jbchem.a126421.
^ Rogers EF (April 1962). "Thiamine antagonists". Annals of the New York Academy of Sciences. 98 (2): 412–429. Bibcode:1962NYASA..98..412R. doi:10.1111/j.1749-6632.1962.tb30563.x. PMID 14493332. S2CID 32281714.

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