Analytical Study of the Reaction of Phenothiazines With Some Oxidants, Metal Ions, and Organic Substances (Review Article)

Kojło, Anatol; Karpińska, Joanna; Kuźmicka, Ludmiła; Misiuk, Wieslawa; Puzanowska-Tarasiewicz, Helena; Tarasiewicz, M.

doi:10.1081/tma-100001461

Cited by 40 publications

(36 citation statements)

References 71 publications

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“…It is marketed under the different brand names as decanoate (e.g., Modecate, Fludecate), enanthate (e.g., Flunanthate) or hydrochloride (e.g., Prolixin, Dapotum, Lyogen). The identification and differentiation of some phenothiazine picrates have been carried out [7] and a review on various aspects of phenothiazines has been published [8].…”

Section: Resultsmentioning

confidence: 99%

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Dutkiewicz

Siddaraju²,

Yathirajan

et al. 2010

J Chem Crystallogr

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The title compound, C 22 H 28 F 3 N 3 OS 2? 9 2(C 6 H 2 N 3 O 7 -) 9 (CH 3 ) 2 SO-the picrate salt of the potent antipsychotic drug, fluphenazine-crystallizes in the triclinic P-1 space group with unit cell parameters a = 10.6333(12) Å , b = 11.9696(12) Å , c = 17.7036 (15) Å , a = 103.265(9)°, b = 98.414(9)°, c = 102.702 (10)°. The ionic fragments: the fluphenazinium dictation, and two picrate anions, are joined by means of strong N-HÁÁÁO and weak C-HÁÁÁO hydrogen bonds into the chains of alternating cations and anions, expanding along [010] direction. Within the chain, the picrates interact by means of short pÁÁÁp interactions: the mean distance between the planes is 3.366 Å ; additional interaction of the same type between one of the picrates and the phenyl ring of the phenothiazine ring system additionally strengthen the pattern. The phenothiazine ring exists in a typical, ''butterflylike'' conformation, with two terminal rings planar and the central ring in a slightly flattened boat form. This conformation results in the dihedral angle between the terminal rings of 41.76(5)°. The aliphatic chain which substitutes phenothiazine at N-position is not in an extended conformation, the torsion angles along this chain are 75.95(14)°a nd -163.96(10)°. The structure contains also the solvent-dimethylsulphoxide molecules, which are connected with the cation-anion structure by means of strong O-HÁÁÁO hydrogen bonds.Keywords Fluphenazine Á Phenothiazines Á Picrates Á Hydrogen bonds Á Crystal packing Experimental PreparationFluphenazine dihydrochloride (5.6 g, 0.01 mol) was dissolved in 25 mL of methanol and picric acid (2.4 g, 0.01 mol) was dissolved in 25 mL of methanol. Both the solutions were mixed and the mixture was stirred in a beaker at 333 K for 1 h and was kept aside for 3 days at room temperature. The formed salt was filtered and dried in vaccum desiccator over phosphorous pentoxide. It was observed that, regardless of the proportions in which the donor and acceptor were mixed, only the 1:2 complex was formed. X-ray quality crystals were obtained from a solution of dimethylsulphoxide after slow evaporation (m.p.: 501-503 K). CrystallographyYellow transparent prism-like crystal (0.2, 0.2, 0.08 mm) was used for data collection. Diffraction data were collected at 120(1) K by the x-scan technique up to 2h = 56.5°, on an Xcalibur Eos diffractometer [1] with graphite-monochromatized MoK a radiation (k = 0.71073 Å ). The temperature

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Section: Resultsmentioning

confidence: 99%

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Dutkiewicz

Siddaraju²,

Yathirajan

et al. 2010

J Chem Crystallogr

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“…14 Phenothiazines were also used as spectrophotometric reagents 2,8 and indicators in various redox titrations with K2Cr2O7, Ce(SO4)2, NH4VO3, KBrO3. 1,3,15 In the presented paper the applications of some oxidizing agents for the spectrophotometric and flow-injection determination of 2,10-disubstituted phenothiazines have been described. with the formation of colored oxidation products.…”

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Efficient Oxidizing Agents for Determination of 2,10-Disubstituted Phenothiazines

Puzanowska-Tarasiewicz

Kuźmicka

Karpińska

et al. 2005

ANAL. SCI.

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“…In order to continue our work on psychotropic drugs analysis [17][18][19][20][21] the aim of the present work is to utilise simple, reliable and accurate extractive spectrophotometric methods for the determination of the antidepressant drug, nortriptyline in pure form and in different pharmaceutical formulations available on the Polish markets. The methods are based on the reaction between this drug with niobium(V) and iron(III) thiocyanate complexes.…”

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Sensitive Extractive Spectrophotometric Methods for the Determination of Nortriptyline Hydrochloride in Pharmaceutical Formulations

Misiuk

Tykocka

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Nortriptyline (NOR) belongs to the family of tricyclic antidepressants, a group of drugs widely used for treating depressive diseases. Its chemical structure is shown in Fig. 1.Most existing methods for the determination of nortriptyline in bulk, pharmaceutical formulations and biological samples have been reviewed. 1) Among other methods described for the assay of this drug are direct UV-spectrophotometry, 2,3) derivatives spectrophotometry, 4,5) fluorimetry 6) and colourimetry. 7,8) The colourimetric methods involve ion association complex with dye-Light Green FCF at pH 5 and Orange II 7) at pH 2 or charge-transfer complex with 7,7,8,8-tetracyanoquinodimethane (TCQN). 8)Extractive spectrophotometric procedures are popular for their sensitivity in the assay of drugs and, therefore, ion-pair extractive spectrophotometry has received considerable attention for the quantitative determination of many pharmaceutical compounds. [9][10][11][12][13][14][15][16] Quantitative analysis of the drugs applying extractive spectrophotometric methods is mainly founded on such factors as type of solvent extraction, nature of coordination agents, acidity of the solution, concentration of reagents, temperature, time of reaction and extraction.Some methodological reports for the determination of nortriptyline 6,7,11,21,[25][26][27] using specrophotometry have been published. However, these methods have several disadvantages in terms of cost performance, consumption of time and essential equipment, difficult reaction conditions and procedures for determination of drugs.For example, De La Pena et al. 6) developed a fast kinetic method for the determination of nortriptyline in pharmaceutical preparations by use of photometric and fluorimetric detection. But the applied procedures required a temperature of 50°C for both types of detection. Obtained linear dynamic ranges of the drug determinations were too broad.Another method 21) was based on oxidation of imipramine and desipramine (drugs related to nortriptyline) with ammonium metavanadate. The method has been developed for determination of the drugs in the visible (VIS) range. However, the applied oxidizing agent cannot be used for determination of nortriptyline in the VIS range. The drug oxidation product is colourless and ammonium metavanadate is an unsuitable agent for its production.Oztunc et al. 8) have proposed a method for nortriptyline determination which exhibited disadvantages in terms of difficult reaction conditions. In this procedure maximum absorption was reached at 80°C and heating time of 10 min was recommended for maximum intensity colour development.Most of the proposed agents for spectrophotometric determination of nortriptyline and related drugs are unsatisfactory for different reasons, e.g., a long period for maximum intensity color development, lengthy and difficult procedure, lack Sensitive Extractive Spectrophotometric Methods for the Determination of Nortriptyline Hydrochloride in Pharmaceutical FormulationsWieslawa MISIUK* and Agnieszka TYKOCKA

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Analytical Study of the Reaction of Phenothiazines With Some Oxidants, Metal Ions, and Organic Substances (Review Article)

Cited by 40 publications

References 71 publications

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

The Crystal Structure of Fluphenazinium Dipicrate Dimethylsulphoxide Solvate

Efficient Oxidizing Agents for Determination of 2,10-Disubstituted Phenothiazines

Sensitive Extractive Spectrophotometric Methods for the Determination of Nortriptyline Hydrochloride in Pharmaceutical Formulations

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