Amitriptylinoxide Research Articles

A new sensing platform for electrochemical assay of amitriptyline based on molecularly imprinted polymer/NiCo2O4 modified carbon cloth

In this study, a new electrochemical sensing strategy is presented for amitriptyline (AMT) by a molecularly imprinted polymer/NiCo2O4 (MIP/NCO) as an electrode modifier on a carbon cloth (CC). The AMT/imprinted polymer ratio was first optimized by means of the density functional theory (DFT) model. The successful formation of the electrode materials was assessed via several characterizations such as X-ray diffraction and Fourier transform infrared spectroscopy. The findings confirmed the nearly complete extraction of the template from the polymer network. The electrochemical properties of the eluted MIP/NCO/CC (EMIP/NCO/CC) were also appraised using cyclic voltammetry (CV) and differential pulse voltammetry (DPV). The constructed sensor demonstrated the superior detection efficiency towards the oxidation of AMT in phosphate buffer solution (PB, pH =7) with a broad linear range from 0.01 μM to 1 μM, a high sensitivity of 58 µA/µM cm2, and a low limit of detection of 2.39 nM. The interfering agents had no significant influence on the detection of AMT. The analysis of AMT in real samples yielded satisfactory results as well. This electrode was particularly well-suited for prospective applications in drug determination owing to its great sensitivity, easy regeneration, and modification with EMIP/NCO.

The development of disposable electrochemical sensor based on MoSe2-rGO nanocomposite modified screen printed carbon electrode for amitriptyline determination in the presence of carbamazepine, application in biological and water samples

The present attempt developed a simple sensing system based on the modification of screen-printed carbon electrode (SPCE) with MoSe2/reduced graphene oxide (rGO) nanocomposite (MoSe2-rGO/SPCE) to voltammetrically co-detect amitriptyline and carbamazepine. Different techniques such as field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FT-IR) were employed to characterize MoSe2-rGO nanocomposite morphology and structure. Moreover, chronoamperometry, differential pulse voltammetry (DPV) and linear sweep voltammetry (LSV) were utilized to explore the electrochemical oxidation of amitriptyline. Data revealed a great current sensitivity for the MoSe2-rGO/SPCE towards amitriptyline. The peak currents of amitriptyline oxidation on the MoSe2-rGO/SPCE had linear dynamic range (0.02–380.0 μM) and a narrow limit of detection (0.007 μM). The MoSe2-rGO/SPCE was successful in sensing carbamazepine and amitriptyline in real specimens, with appreciable recovery rates.

Voltammetric Amitriptyline Determination Using a Metal-Free Electrode Based on Phosphorus-Doped Multi-Walled Carbon Nanotubes

A new electrode material of phosphorus-doped multi-walled carbon nanotubes (P-MWCNTs) was developed as an electrochemical sensing element for amitriptyline (AMT). P-MWCNTs were hydrothermally synthesized and drop casted on a glassy carbon electrode (P-MWCNTs/GCE). The P-MWCNTs were morphologically, chemically and structurally characterized. The electrochemical characteristics of the P-MWCNTs/GCE were investigated by cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and adsorptive stripping voltammetry (AdSV). The P-MWCNTs increased electron transfer at the GCE and the electrochemical conductivity of the electrode. Electrocatalytic activity toward the oxidation of AMT was excellent. In the optimal voltammetric condition, the P-MWCNTs/GCE produced linear ranges of 0.50 to 10 μg ml−1 and 10 to 40 μg ml−1. The limit of detection (LOD) and limit of quantification (LOQ) were 0.15 μg ml−1 and 0.52 μg ml−1, respectively. The developed sensor displayed good repeatability, reproducibility and specificity. The sensor successfully quantified AMT in pharmaceutical tablets, giving results consistent with spectrophotometric analysis. The sensor achieved recoveries from 98 ± 2% to 101 ± 5% from spiked urine samples. The proposed sensor could be applied to determine AMT in pharmaceutical and urine samples for forensic toxicology.

Determination of Amitriptyline on a Carbon Nanocomposite Ionic Liquid Electrode

This manuscript reports oxidation of amitriptyline at the carbon nanocomposite ionic liquid electrode fabricated using multi-walled carbon nanotubes and the ionic liquid 1-octylpyridinium hexafluorophosphate. The surface morphology of the electrode was characterized by scanning electron microscopy. Differential pulse voltammetry was applied as an analytical procedure for the determination of the sub-micromolar concentration of amitriptyline. Different experimental parameters were optimized. Considering optimized conditions, the proposed electrode represented remarkable sensitivity toward determination of amitriptyline compared to other conventional electrodes and linearity in the range from 5 × 10–8 to 9 × 10–5 was obtained for amitriptyline with the detection limit of 1.9 × 10–8 M. Cyclic voltammetry was applied to obtain information about the reaction mechanism and calculating some kinetic parameters. The oxidation process was irreversible and showed adsorption-controlled behavior. The method was successfully applied for the quantification of amitriptyline in pharmaceuticals forms.

Electrocatalytic Behavior and Determination of Amitriptyline Drug with MWCNT@Celllulose Composite Modified Glassy Carbon Electrode.

A novel nanocomposite of cellulose based on multiwalled carbon nanotube (MWCNT) was synthesized by a simple solution mixing–evaporation method. The morphology, thermal investigations, electrocatalytic oxidation of amitriptyline were analyzed at multi-walled carbon/cellulose nanocomposite in detail. The amitriptyline (AMT) drug was electrochemically studied in a phosphate buffer at different pH using the MWCNT/cellulose modified glassy carbon electrode (GCE). As per the linear relationship among AMT along with peak current, differential pulse voltammetry technique has been established for their quantitative pharmaceutical’s determination. The oxidation potential shifted negatively compared to GCE, showing that the MWCNT/cellulose modified electrode had an excellent catalytic activity for the AMT oxidation. The anodic peak current varied linear response with AMT’s concentration in the range of 0.5 to 20.0 μM with a LOD of 0.0845 μM and LOQ of 0.282 μM, respectively. The proposed method was effectively put on the determination of AMT in pharmaceutical and urine samples. This novel methodology is presented here as an example of a complete development methodology for the determination of amitriptyline drug and sensor for use in healthcare fields.

Oxidation of amitriptyline and nortriptyline by ferrate(VI): efficiency and reaction pathways

The oxidation of amitriptyline (AMI) and nortriptyline (NOR), two typical tricyclic antidepressants, has been studied in ferrate(VI) (Fe(VI)) solution. The removal rate of AMI and NOR increased with increasing Fe(VI) dosage and was seen to be pH dependent in the order pH 7.0 < 10.0 < 8.0 < 9.0. UV irradiation at 254nm was found to exert a synergistic effect on the Fe(VI) oxidation of AMI and NOR. By LC–ESI-MS/MS analysis, the main oxidation products of AMI and NOR by Fe(VI) have been identified. The exocyclic double bond is first oxidized to give the exo-epoxide, which is then hydrolyzed and finally oxidized to give dibenzosuberenone and 3-dimethylamino-propionaldehyde. The results suggest that Fe(VI) has a good ability to oxidize AMI and NOR in aqueous solution and could be an effective treatment method for the purification of waters containing these particular antidepressants.

Oxidation of Tricyclic Antidepressant Agent, Amitriptyline, by Permanganate in Sulphuric Acid Medium: Kinetic and Mechanistic Approach

The kinetics of oxidation of amitriptyline by potassium permanganate in aqueous sulphuric acid medium at 298K and at a constant ionic strength of 0.20 mol dm-3 has been investigated spectrophotometrically. The reaction exhibits 5:4 stoichiometry (5 Amitriptyline:4 KMnO4). The reaction was first order with respect to manganese(VII) concentration. The order with respect to amitriptyline was found to be less than unity (0.80). Increase in acid concentration increased the rate. The order with respect to acid concentration was also less than unity (0.40). The effect of added products, ionic strength and dielectric constant have been studied on the rate of reaction. The oxidation products were identified by using 2,4 DNP derivative, IR, GCMS spectral studies. A suitable mechanism was proposed on the basis of experimental results. The reaction constants involved in the different steps of the reaction mechanism were calculated. The activation parameters with respect to slow step of the mechanism was determined and discussed.

Ruthenium(III) Catalyzed Oxidative Degradation of Amitriptyline-A Tricyclic Antidepressant Drug by Permanganate in Aqueous Acidic Medium

The oxidation of amitriptyline by potassium permanganate has been investigated spectrophotometrically in the presence of ruthenium(III) as catalyst in aqueous acidic medium at a constant ionic strength of 0.20 mol⋅dm−3. The stoichiometry was found to be 1:1 in terms of the mole ratio of amitriptyline and permanganate ions consumed. The order of the reaction with respect to manganese(VII) and ruthenium(III) concentration was unity while the order with respect to amitriptyline was less than unity over the concentration range studied. The rate increased with an increase in acid concentration. The reaction rates revealed that the Ru(III) catalyzed reaction was about eight-fold faster than the uncatalyzed reaction. The oxidation products were identified by spectral analysis. A tentative mechanism consistent with the kinetics has been proposed. The reaction constants involved in the different steps of the reaction mechanism were calculated. Kinetic experiments suggest that HMnO4 is the reactive permanganate species and [Ru(H2O)6]3+ is the reactive Ru(III) species.

Bis -(3,5-dimethyl-pyrazolyl-1-methyl)-(3-phosphanyl-propyl)-amine complexes of copper(II), nickel(II), and cobalt(II)

A series of Cu(II), Co(II), and Ni(II) complexes of bis-(3,5-dimethyl-pyrazolyl-1-methyl)-(3-phosphanyl-propyl)-amine C15H26N5P (1), prepared from 3-aminopropylphosphine and 1-hydroxymethyl-3,5-dimethylpyrazole were characterized. The nature of bonding and the geometry of the complexes have been deduced from elemental analysis, infrared, electronic, 1H NMR, 31P NMR spectra, magnetic susceptibility, and conductivity measurements. The studies indicate octahedral geometry for nickel complex and square pyramidal geometry for copper and cobalt complexes. The EPR spectra of copper complex in acetonitrile at 300 K and 77 K were recorded. Biological activities of the ligand and metal complexes have been studied on Staphylococcus aureus, Escherichia coli, Aspergillus niger, and Aspergillus flavus by well-diffusion method. The zone of inhibition values were measured at 37°C for a period of 24 h. The electrochemical behavior of copper complexes was studied by cyclic voltammetry. Catalytic study indicates the copper complex has efficient catalytic activity in oxidation of amitriptyline.

The Metabolic Fate of Amitriptyline, Nortriptyline and Amitriptylinoxide in Man

Amitriptyline (AT), the most widely used tricyclic antidepressant, undergoes oxidative metabolism in the side chain with production of the secondary amine nortriptyline (NT), a primary amine, and the N‐oxide amitriptylinoxide (AT‐NO); in addition, direct conjugation leads to a quaternary ammonium‐linked glucuronide. Hydroxylation of AT or NT at the ethylene bridge of the central seven‐membered ring results in four isomeric alcohols and occurs with high stereo‐ and enantioselectivity, the (−)‐(E)‐10‐hydroxy compounds usually being the major products. The disposition of the alcohols is also partially enantioselective, for instance with regard to glucuronidation and reversible oxidation to ketones. Introduction of a second hydroxy group results in isomeric glycols. Oxidative attack at an aromatic ring is a minor pathway leading to dihydrodiols and phenols. Numerous metabolites originate by combinations of reactions in the ring system and the side chain. AT‐NO is by about one‐third excreted in unchanged form or as 10‐hydroxy derivative; the major part is reduced to AT and metabolized further. The review covers current knowledge on the enzymes participating in the individual pathways. Their quantitative importance is inferred from kinetic studies in volunteers and patients and from experiments in vitro. Clinical consequences of biochemical findings mainly derive from the impact of the polymorphic CYP2D6 mediating (−)‐(E)‐10‐hydroxylation and from its potential inhibition by other psychoactive drugs.

Auditory event-related potentials in the course of antidepressant treatment: Latencies

1. 1. In depressive patients (DSM-III-R) treated with amitriptyline or amitriptylin oxide, the authors evaluated cognitive functions and auditory event-related potentials (AERP) before (n = 29) and after therapy (n = 17). 2. 2. AERP were elicited by an oddball paradigm. Cognitive functions were evaluated by the Zahlen-Verbindungs-Test, the Zahlen-Symbol-Test, and the Benton-Test. 3. 3. The latency of N1 seemed to be increased significantly with therapy. This is discussed in the context of a processing negativity. 4. 4. The latency of the endogenous component P3 (P300) was found to be increased with cognitive disturbances and with age but not related to mood score. It was decreased significantly with therapy. 5. 5. The registration of P3 latency is an appropriate method to demonstrate cognitive impairment and improvement with therapy in a depressive episode.

Auditory event-related potentials in the course of antidepressant treatment: amplitudes

1. 1. In depressive patients (DSM-III-R) treated with amitriptyline or amitriptylin oxide, the authors evaluated cognitive functions and auditory event-related potentials (AERPs) before (n = 29) and after therapy (n = 17). 2. 2. AERPs were elicited by an oddball paradigm. Cognitive functions were evaluated by the Zahlen-Verbindungs-Test, the Zahlen-Symbol-Test, and the Benton-Test. 3. 3. The amplitudes of the components N1, N2, and P3 showed a negative correlation with age and cognitive disturbances. The amplitude of N2 and the interpeak amplitudes N2/P3 and P3/slow wave were decreased with higher depression score. 4. 4. After treatment, the amplitude of N2 was increased and the sum of all peaks shifted to more negative values. 5. 5. The results suggest that the AERP amplitudes may reflect improvement from depression with special aspects of mood, cognition and drug profile.

Amitriptylinoxide

Amitriptylinoxide

Detection of 3,3'-spirobiphthalide from the oxidation of amitriptyline

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDetection of 3,3'-spirobiphthalide from the oxidation of amitriptylineA. W. Missen and H. M. StoneCite this: Anal. Chem. 1977, 49, 12, 1864Publication Date (Print):October 1, 1977Publication History Published online1 May 2002Published inissue 1 October 1977https://doi.org/10.1021/ac50020a058RIGHTS & PERMISSIONSArticle Views34Altmetric-Citations2LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (111 KB) Get e-Alerts Get e-Alerts

Studies on the oxidation of amitriptyline.

The quantitative determination of amitriptyline extracted from biological fluids has been achieved using an oxidation procedure. By use of selective oxidation methods a knowledge of the levels of 10-hydroxylated metabolites of amitriptyline can be obtained. Some evidence is presented that dehydroamitriptyline, or its demethylated derivatives, are natural metabolites of amitriptyline in man.

Binding and oxidation of amitriptyline and a series of its oxidized metabolites in liver microsomes from untreated and phenobarbital-treated rats.

1. The tricyclic antidepressant drug amitriptyline and its oxidized metabolites elicit the type I spectral change in rat liver microsomes and have low spectral dissociation constants (Ks-values), indicating that they bind with high affinities to cytochrome P-450. The Ks-values of these substrates are related to their RF-values on t.l.c.—a low Ks-value corresponding to a high RF-value and vice versa. This suggests that the ability of these compounds to interact with microsomal P-450 is dependent on their physical-chemical properties2. The Ks-value of amitriptyline increases with increasing concn. of microsomal protein, and the max. magnitude of the type I spectral change is reached when the molar concn. ratio amitriptyline/P-450 is very low (range: 0.98–2.8). Desmethylnortriptyline elicits the type I spectral change at low concn. (<2 μM), but a type II change at higher concn. (>2 μM). At max. type I change, just before the ‘type II absorbancy peak’ at 434 nm appears, the incubation system contains about one mol of desmethylnortriptyline per mol of P-450.3. The rate of oxidation of a parent compound is more rapid than that of its oxidized metabolites, and the rates of demethylation of amitriptyline, 10-hydroxy-amitriptyline and nortriptyline correlate with their Ks-values. The 10-hydroxylation of desmethylnortriptyline is very slow at substrate concn which cause the type II spectral change. Upon incubation of 10-hydroxynortriptyline, 10-oxo-nortriptyline was found and identified by mass fragmentography. This might reflect the formation of the metabolite 10,11-dihydroxynortriptyline, which upon derivatization for g.l.c. is dehydrated to 10-oxo-nortriptyline.4. Phenobarbital treatment of rats increases the rate of demethylation of amitriptyline, but decreases the 10-hydroxylation of nortriptyline. Amitriptyline elicits the type I spectral change in microsomes from phenobarbital-treated animals, as in ‘control’ microsomes, but nortriptyline elicits an atypical type II spectrum. Desmethylnortriptyline elicits only the type II change in the phenobarbital microsomes. The results indicate that phenobarbital induces qualitative alterations of cytochrome P-450 and/or its microenvironment.5. Since both amitriptyline and its oxidized metabolites seem to interact with cytochrome P-450, it is plausible that these compounds influence each others metabolism by competition for microsomal interaction. Such possible interactions should be kept in mind when analyzing factors influencing the total fate of a drug and its metabolites.