Synthesis of possible metabolites of chlorpromazine. I. 7‐hydroxy derivatives of chlorpromazine, nor<sub>1</sub>‐chlorpromazine and nor<sub>2</sub>‐chlorpromazine

Nodiff, Edward A.; Ina, Shuichiro; Oda, Noriichi; Hayazaki, Takanori; Nishibe, Sansei; Kohno, Takayuki; Hausman, M.; Manian, Albert A.

doi:10.1002/jhet.5570040212

Cited by 12 publications

References 9 publications

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The Smiles and Related Rearrangements of Aromatic Systems

2011

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In 1894, Henriques reported that bis(2‐hydroxy‐1‐naphthyl) sulfide was converted to an isomeric dibasic substance by treatment with alkaline ferricyanide and a subsequent reduction of the intermediate obtained. Hinsberg carried out a similar sequence of reactions with bis(2‐hydroxy 1 naphthyl) sulfone. The structures of the isomeric products of the two series were established by Smiles who recognized the occurrence of a novel intramolecular nucleophilic rearrangement. This chapter surveys the reactions, which because of the extensive work of Smiles, have been called Smiles rearrangements. They may be characterized as intramolecular displacements at aromatic rings initiated by nucleophilic centers located two or three atoms distant from the functional group which is displaced.

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The Smiles and Related Rearrangements of Aromatic Systems

2011

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Determination of chlorpromazine and its major metabolites by gas chromatography/mass spectrometry: Application to biological fluids

Gruenke

Craig

Klein

et al. 1985

Biol. Mass Spectrom.

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A method for the quantitative determination of chlorpromazine and five of its major metabolites in a single sample of biological fluid in the ng/ml range has been developed utilizing gas chromatography/mass spectrometry with selected ion recording. The assay is highly specific and quantification is accomplished by an inverse stable isotope dilution technique, using deuterium-labeled variants of the compounds as internal standards. In this way the concentrations of chlorpromazine and five of its major metabolites (the sulfoxide, the N-oxide, the monodemethylated, the didemethylated, and the 7-hydroxylated compounds) can be determined in biological fluids. Levels in humans have been measured both in plasma and in red blood cells and are compared to those found in related in vitro studies.

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Nickel‐Catalyzed C−H Chalcogenation of Anilines

Müller

Ackermann

2016

Chemistry A European J

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The C-H thiolation of aniline derivatives was accomplished with a versatile nickel(II) catalyst under ligand-free conditions. The robust nature of the nickel catalysis system was reflected by the C-H thiolation with a good functional group tolerance and an ample scope, employing anilines possessing removable directing groups. The widely applicable nickel catalyst also allowed for aniline C-H selenylations, while mechanistic studies provided strong support that the rate-determining step is the C-H activation.

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Synthesis of possible metabolites of chlorpromazine. I. 7‐hydroxy derivatives of chlorpromazine, nor₁‐chlorpromazine and nor₂‐chlorpromazine

Abstract: The title compounds and various derivatives have been prepared as analytical standards for the identification of chlorpromazine metabolites in biological materials. Additional evidence is presented for the existence of a halogen‐induced Smiles rearrangement in the phenothiazine series.

Cited by 12 publications

References 9 publications

The Smiles and Related Rearrangements of Aromatic Systems

The Smiles and Related Rearrangements of Aromatic Systems

Determination of chlorpromazine and its major metabolites by gas chromatography/mass spectrometry: Application to biological fluids

Nickel‐Catalyzed C−H Chalcogenation of Anilines

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Synthesis of possible metabolites of chlorpromazine. I. 7‐hydroxy derivatives of chlorpromazine, nor1‐chlorpromazine and nor2‐chlorpromazine

Abstract: The title compounds and various derivatives have been prepared as analytical standards for the identification of chlorpromazine metabolites in biological materials. Additional evidence is presented for the existence of a halogen‐induced Smiles rearrangement in the phenothiazine series.

Cited by 12 publications

References 9 publications

The Smiles and Related Rearrangements of Aromatic Systems

The Smiles and Related Rearrangements of Aromatic Systems

Determination of chlorpromazine and its major metabolites by gas chromatography/mass spectrometry: Application to biological fluids

Nickel‐Catalyzed C−H Chalcogenation of Anilines

Contact Info

Product

Resources

About

Synthesis of possible metabolites of chlorpromazine. I. 7‐hydroxy derivatives of chlorpromazine, nor₁‐chlorpromazine and nor₂‐chlorpromazine