10404-90-7

Upstream product

• 969-99-3 chlorpromazine sulfoxide 
• 92-39-7 2-chlorophenothiazine 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 69-09-0 chlorpromazine hydrochloride 
• 1672-76-0 Chlorpromazine oxide 
• 50-53-3 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine 

Relevant academic research and scientific papers

Synthesis and synergistic antimycobacterial screening of chlorpromazine and its metabolites

The antimycobacterial activities of chlorpromazine and its metabolites were evaluated alone and in combination with antitubercular drugs. Although associated with limited antimycobacterial activity when tested individually, chlorpromazine and its metabolites exhibited clear synergy when tested in combination with a number of aminoglycosides as well as the active metabolite of rifampicin, 25-desaceteylrifampicin. The combination of chlorpromazine and spectinomycin was associated with the greatest synergy, yielding a fractional inhibitory concentration index (FICI) of 0.31. Synergistic interactions were also observed for combinations of 7-hydroxychlorpromazine or nor-chlorpromazine with kanamycin, streptomycin, spectinomycin and 25-desacetylrifampicin (FICI 0.19-0.5).

Metabolism of phenothiazines: identification of N oxygenated products by gas chromatography and mass spectrometry

The solid inlet mass spectra of N oxide and N oxide sulfoxide metabolites of promazine, chlorpromazine and levomepromazine (methotrimeprazine) have been determined at different temperatures and compared with the mass spectra of the main thermolytic product of the N oxides and N oxide sulfoxides obtained during combined gas chromatography mass spectrometry. Diagnostic ions were produced by direct insertion of the compounds at ambient temperature into the mass spectrometer. These ions distinguish the N oxides of arylalkyl tertiary amines from the N oxygenated derivatives of primary and secondary arylalkylamines.

Synthesis of the N-oxides of phenothiazine antipsychotic agents

Chlorpromazine N-oxide, fluphenazine N(4')-oxide, prochlorperazine N(4')- oxide, sulforidazine N-oxide, and trifluoperazine N(4')-oxide were synthesized by oxidation of the designated nitrogen atom in the N-10 side chain of the respective parent drug with 3-chloroperoxybenzoic acid. In the case of trifluoperazine, a stepwise increase in the amount of oxidant yielded the N(1'),N(4')-dioxide and N(1'),N(4'),S-trioxide. The N',S-dioxides of chlorpromazine and sulforidazine were obtained by hydrogen peroxide oxidation of the appropriate parent drug.