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Allithiamine

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Chemical compound

Pharmaceutical compound

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^N
PubChemCID	3037212
ChemSpider	2301021^Y
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-^Y Key:WNCAVNGLACHSRZ-KAMYIIQDSA-N^Y
^NY (what is this?) (verify)

Allithiamine (thiamine allyl disulfide orTAD) is alipid-soluble form ofvitamin B₁ which was discovered ingarlic (Allium sativum) in the 1950s along with itshomolog prosultiamine.^[1] They were both investigated for their ability to treatWernicke–Korsakoff syndrome andberiberi better thanthiamine.^[2]

^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.

Fat
soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin^#
D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol^# 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol
E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan
K (B02B)	Naphthoquinone Phylloquinone (K₁)^# Menaquinones (K₂) Menadione (K₃)^‡ Menadiol and derivatives (K₄) 4-Amino-2-methyl-1-naphthol (K₅)^‡ 2-Methylnaphthalene-1,4-diamine (K₆) 4-Amino-3-methyl-1-naphthol (K₇)