Synthesis of the beta-D-glucuronides of 2,3-, 3,4-, and 2,6-dichlorophenol.

The beta-D-glucuronides of 2,3-, 3,4-, and 2,6-dichlorophenol (1-3) were prepared by a modified Koenigs-Knorr synthesis. As the alkaline hydrolysis of perpivaloylated methyl (2,3-dichlorophenyl)-glucuronate 1a led to a dehydrated glucuronide, the preparation of peracetylated methyl dichlorophenylglucuronates with subsequent cleavage of the ester bindings under mild conditions was preferred.

[Discrepant results with immunohistochemical detection TDx/ADx?].

In the last 2 years we had some problems to confirm the thin-layer results (amphetamines, opiates, benzodiazepines, barbiturates and cocaine) with the immunoassay system TDx/ADx. Between January 1989 and December 1990 we did 883 screenings in urine samples (pre- and postmortal) and had 157 discrepancies (20%). In regard of the high level of discrepancies, we had to test the compatibility of TDx and ADx, their detection limits and compared the results with a second method, thin-layer chromatography.

[Isolation of chlorphenoxamine metabolites in human urine and their identification].

After the administration of chlorphenoxamine (2-[1-(4-chlorophenyl)-1-phenylethoxy]-N,N-dimethylethanamine++ +, Systral) (I) the following compounds have been detected in human urine. They were identified as chlorphenoxamine (I), N-demethyl-chlorphenoxamine (II), chlorphenoxamine-N-oxide (III), 1-(4-chlorophenyl)-l-phenylethanol (IV), 1-(4-chlorophenyl)-1-(4'-hydroxyphenyl)-ethanol (V), 1-(4-chlorophenyl)-1-(4'-hydroxyphenyl)-ethene (VI), 1-(4-chlorophenyl)-1-(4'-hydroxy-3'-methoxyphenyl)-ethanol (VII), 1-(4-chlorophenyl)-1-(4'-hydroxy-3'-methoxyphenyl)-ethene (VIII), 2-[1-(4-chlorophenyl)-1-(4'-hydroxyphenyl)-ethoxy]-N-methyl-ethanamine (IX) and 2-[1-(4-chlorophenyl)-1-(4'-hydroxy-3'-methoxyphenyl-ethoxy]- N-methylethanamine (X). The compounds IV, V, VI, VII, VIII, IX and X were also found to be excreted as conjugates.

[Cleavage of 2-phenylpropan-1-ol and 2-phenylpropan-2-ol-glucuronide, 2 metabolites of isopropylbenzol (Cumol)].

The behaviour of 2-phenyl-1-propanol (I) and 2-phenyl-2-propanol (II) and their glucuronides with HCl has been investigated. While I shows a high acidic constancy, II undergoes a partial conversion into 2-phenylpropane (III) which itself yields numerous products. The glucosidic bond of glucuronide I is quantitatively split by 10.