Confirmation of the enantiomers of 1-methyl-1,2,3,4-tetrahydroisoquinoline in the mouse brain and foods applying gas chromatography/mass spectrometry with negative ion chemical ionization.
With the aid of a new chiral derivatizing reagent and a sensitive and specific assay using capillary gas chromatography/negative ion chemical ionization mass spectrometry, the proportions of R and S enantiomers of 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) in mammalian tissues and foods were studied. R- and S-1MeTIQ enantiomers derivatized with a chiral derivatizing reagent, perfluoro-2-propoxypropionylchloride, were clearly separated. The ratio of enantiomers was R/S = 0.24, 0.55 and 0.60 in wine, cocoa and mouse brain. S-1MeTIQ predominated in all samples. This result suggested that 1MeTIQ could be formed at least partially through an enzymatic mechanism.
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Y
Y
Makino
Y
Y
Tasaki
S
S
Ohta
M
M
Hirobe
D000818:Animals; D001923:Brain Chemistry; D002099:Cacao / Q000032:analysis*; D002849:Chromatography, Gas; D007546:Isoquinolines / Q000032:analysis* / Q000138:chemical synthesis; D008297:Male; D013058:Mass Spectrometry; D051379:Mice; D008810:Mice, Inbred C57BL; D010945:Plants, Edible / Q000032:analysis*; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines; D014920:Wine / Q000032:analysis*
D007546:Isoquinolines; D044005:Tetrahydroisoquinolines; C050386:1-methyl-1,2,3,4-tetrahydroisoquinoline