Aromatic oxidation of some phenothiazines.
The previously reported N-oxidation products phenothiazine-N-OH, N-O. and -NOOH obtained upon chemical and metabolic oxidation of phenothiazine nuclei are now shown to be the C-oxidation products, 7-hydroxyphenothiazines, phenothiazin-3-ones and phenothiazin-7-ones which have the para-hydroquinoneimino and para-quinoneimino type systems. 2. The metabolism of various 2-substituted phenothiazines in vitro gave mainly ring-hydroxylated metabolites and sulphoxides. The phenolic metabolites were further oxidized to phenothiazones either as metabolites or as 'metabonates'. 3. After metabolism of chlorpromazine, nor1-chlorpromazine and nor2-chlorpromazine in vitro, phenothiazones ('pink compounds') were obtained as N-dealkylated products of the phenolic derivatives 7- or 3-hydroxy compounds. 4. The synthesis and physicochemical characteristics including t.l.c., u.v., g.l.c. and mass spectra of the oxidized phenothiazine nuclei and of 8-(N-methyl-anilino)-2-chlorophenothiazin-7-one are reported.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D006168:Guinea Pigs; D006900:Hydroxylation; D066298:In Vitro Techniques; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D010084:Oxidation-Reduction; D010640:Phenothiazines / Q000138:chemical synthesis / Q000378:metabolism*; D011817:Rabbits
D010640:Phenothiazines