Phenothiazine compounds

DiMascio, A., Haven, L.L., Klerman, G.L. The psychopharmacology of phenothiazine compounds a comparative study of the effects of chloipromazine in normal males. J. Nerv. Ment. Dis. 13b, 15-28, 168-186, 1963. 

Amitriptyline hydrochloride and imipramine hydrochloride are similar in structure, with the exception of the nitrogen in the center ring, and belong to the family of phenothiazine compounds. Finally, the two-carbon bridge linking the aromatic rings may be ethyl (-CH2CH2-) or ethylene (-CH=CH-). 

Table 2 shows the phenothiazine compounds tested by Dastidar, Chakrabarty and their group for detection of antimicrobial action along with the names of industries which supplied these compounds in pure, dry powder form. The table also provides specific references. 

Wang, J. Freiha, B.A. Deshmukh, B.K. Adsorptive extractive stripping voltammetry of phenothiazine compounds at carbon paste electrodes. Bioelectrochem. Bioenerg. 1985, 14, 457-467. 

Chlorpromazine Hydrochloride, USP. Chloiprono-zinc hydrochloride. 2-chloro-IO-[.T-(dimethylamino) )io-pyljphenothiuziiK monohydrochloride (Thorazine), waslle first phenothiazine compound introduced into therapy. II i<... 

Fig. 25. A comparison of the distribution and excretion of two antihistamines, the tertiary promethazine (a) and the quaternary (Aprobit) phenothiazine compound (6) labeled with3sS. Note the high concentrations of the tertiary amine in brain tissue and the restriction in the distribution of the quaternary compound mainly to the liver and the intestines. After Hansson and Schmiterlow145 ...

In the treatment of paludism, a series of newly synthesized phenothiazine compounds were found to inhibit the growth of both chloroquine-sensitive and chloroquine-resistent strains of Plasmodium falciparum. The antimalar-ial activity of these phenothiazines increased with the number of alkaline groups located in the alkylamino side chain. Also, phenothiazine, chloropro-mazine and other novel phenothiazine compounds inhibited the formation of (1-hematin, in a way similar to chloroquine [120]. 

In another type of medical study, some phenothiazine derivatives were prepared in order to obtain a drug permitting the prevention and/or treatment of hearing impairment [ 121,122], The efficiency of these phenothiazine compounds (Fig. 9) in the treatment of damage to the cochlea was investigated. The developed drug was protected by patents [121,122],... 

Fig. 9 Structure of phenothiazine compounds (R = H, alkyl, aralkyl, etc.) used in medicine for preventing and/or treating hearing loss...

Nichols et al. [ 144] patented some combinations of drugs including phe-nothiazines for the treatment of neoplasms. This invention provided formulations and structural modifications for phenothiazine compounds, resulting in altered biodistribution, thereby reducing the occurrence of adverse reactions associated with this class of drugs. 

Imipramine is structurally analogous to chlorpromazine but the replacement of sulphur by a —CHj - CH2— linkage causes a considerable change in steric and electronic geometry and in pharmacological activity. Like the phenothiazine compounds, imipramine shows some activity against acetylcholine, noradrenaline and histamine , and extrapyramidal side effects... 

The accidental discovery of psychotropic properties among a number of different compounds has been exploited by chemists to produce a huge range of psychotropic drugs, a few of which have been discussed in this review. While there can be no doubt that some of them have been of the greatest therapeutic value—the treatment of schizophrenia, for instance, has been revolutionized by the phenothiazine compounds—others have failed to... 

Wallace, J.E. Shimek, E.L.J. Stavchansky, S. Harris, S.C. Determination of promethazine and other phenothiazine compounds by liquid chromatography wih electrochemical detection. Anal.Chem., 1981, 53, 960-962... 

Dimethylaminopropyl) phenothiazine compound of 8-chlorotheophylline Promethazine chlorotheophyllinate BP BPC USP ... 

It enjoys the reputation for being the tranquilizer of the phenothiazine compounds. It is found to be efiective in the management of manifestations of psychotic disorders and manic depressive illness manicpahse), apprehension and anxiety and prior to surgery. It is also used for the treatment of moderate to severe agitation. 

The development of the tricyclic antidepressants arose out of work carried out on phenothiazine compounds related to chlorpromazine. The earlier molecules possessed two benzene rings joined by a third ring of carbon atoms, with sometimes a nitrogen, and had antidepressant activity, hence their name. Some of the later antidepressants have one, two or even four rings. Table 34.1 , (see below) lists the common tricyclic antidepressants, the selective serotonin reuptake inhibitors (SSRIs) and a number of other drugs that are also used for depression. 

Methylene blue is 3,7-bis-(dimethylamino)phenozathionium chloride tetramethyl thionin chloride, a phenothiazine derivative used in various ways as shown in Table 9. In one observed individual who had acquired a photosensitivity from a phenothiazine compound, the administration of methylene blue urinary antiseptic produced a flare of the photodermatitis. 

In 2005, Dahn et al. from Dalhousie University discovered that 2,5-di-tcrt-butyl-1,4-dimethoxybenzene (144) can be used as an additive in small quantities in batteries with LiFeP04 cathodes [138], Furthermore, in 2006, the same researchers discovered that phenothiazine compounds, such as 10-methylphenothiazine (145), can be used as additives in small quantities [139],... 

Common strong oxidants are used to obtain colored products by acting directly on the pharmaceutical, e.g., Ce(IV), Cr(VI), metavanadate, BrOT, N-bromosuccinimide, and chloramine-T. Direct oxidation of imipramine and desipramine by ammonium metavanadate allows its determination in pharmaceutical dosage forms. The quantitative estimation of 11 phenothiazine drugs in dosage forms is also based on the interaction of these phenothiazine compounds with diphenylamine in presence of N-bromosuccini-mide and sulfuric acid. Most of the studied phe-nothiazines yield bluish green products and the color is stable for at least 1 h. 

Table 100. Explanations for the hRf-values in Table 99 for phenothiazines, compounds of similar structure to phemthiazines, diaz pines ... 

Determination of Some Phenothiazine Compounds in Plasma by Gas Chromatography with Specific Detector for Nitrogen Compounds Rev. Chim. (Bucharest) 31(5) 492-494 (1980) CA 93 106698u... 

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