119558-21-3

Basic information

• Product Name: (3R,4R)-4-hydroxy-4-(3-methoxyphenyl)-1-methyl-3-[(trimethylammonio)methyl]tetrahydro-2H-thiopyranium diiodide (non-preferred name)
• CAS NO: 119558-21-3
• Molecular Formula: C₁₇H₂₉NO₂S*2I
• Molecular Weight: 565.2916
• Mol File: 119558-21-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,4R)-4-hydroxy-4-(3-methoxyphenyl)-1-methyl-3-[(trimethylammonio)methyl]tetrahydro-2H-thiopyranium diiodide (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-4-hydroxy-4-(3-methoxyphenyl)-1-methyl-3-[(trimethylammonio)methyl]tetrahydro-2H-thiopyranium diiodide (non-preferred name)(119558-21-3)
• EPA Substance Registry System: (3R,4R)-4-hydroxy-4-(3-methoxyphenyl)-1-methyl-3-[(trimethylammonio)methyl]tetrahydro-2H-thiopyranium diiodide (non-preferred name)(119558-21-3)

Safety Data

• Hazardous Substances Data: 119558-21-3(Hazardous Substances Data)

Upstream product

• 41533-19-1 3-(N,N-Dimethylaminomethyl)-tetrahydro-4H-thiopyran-4-on 
• 1072-72-6 Tetrahydrothiopyran-4-one 
• 112775-98-1 3-((dimethylamino)methyl)-4-(3-methoxyphenyl)tetrahydro-2H-thiopyran-4-ol 
• 74-88-4 methyl iodide 

Relevant articles and documents

4-ARYL-3-(DIMETHYLAMINOMETHYL)THIACYCLOHEXAN-4-OLS INCLUDING THE THIA ANALOGUE OF TRAMADOL; SYNTHESIS AND ANALGETIC ACTIVITY

Mannich reaction of thiacyclohexan-4-one with dimethylamine and paraformaldehyde afforded 3-(dimethylaminomethyl)thiacyclohexan-4-one (XIV) which was subjected to reactions with a series of arylmagnesium bromides.The products were mixtures of trans- and cis-amino alcohols III-XII from which the predominating trans-components were mostly obtained by crystallization of hydrochlorides or chromatography of bases.The tramadol (I) analogue, i.e. the 3-methoxy compound V, was prepared in the form of both racemates and their relative configuration was confirmed by the IR spectra.Compound V was demethylated to the 3-hydroxyphenyl analogue XIII, transformed to the bis-onium salt XVI, partially N-demethylated to the N-monodemethyl analogue XVII, and oxidized to the sulfoxide XX and to the sulfone N-oxide XXI.Some of the amino alcohols (III-V, VIII, IX, XIII) showed clear analgetic activity in the writhing syndrome inhibition test in mice; the 3-methoxy and 3-hydroxy compounds (V and XIII) were the most active ones, the latter being slightly more active than tramadol (I).