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Temperature is an essential physical characteristic that influences all biological processes. Building on previous research on dialkylamino-functionalized rhodamine-based thermo-sensors, we investigate herein the thermosensitive properties of triamino-phenazinium dyes. Through a simple five-step synthetic route, we synthesized amino-phenazinium chromophores 6 and 7, featuring diethylamine substituents at different positions. A comparative analysis of optical properties and thermosensitivity was conducted on these compounds and an isomer, 5, in which butylamine moiety replaced the diethylamine group. The different emissive behaviors of the three fluorophores emphasize that not only the chemical nature but also the specific position of the alkylamine substituent play fundamental roles in the synthesis of highly emissive thermo-probes. [ABSTRACT FROM AUTHOR]

The present work was performed with the objective of novel topical formulation development of poorly watersoluble drug Diclofenac diethylamine by loading the drug-containing nanosponge into the topical formulation. The nanosponges are polymeric nanoparticles that entrap the drug. The drug-loaded nanosponge has different absorption characteristics in comparison to the pure drug in the topical drug delivery system. The drug was first loaded in the ethylcellulose nanosponge using the emulsion solvent diffusion method. Then Diclofenac diethylamine nanosponge-loaded topical gel formulations were developed by using Carbopol 940 as a gel-forming polymer. The Diclofenac diethylamine-loaded nanosponges were evaluated for various evaluation parameters such as particle size distribution, surface morphology, drug entrapment efficiency, polydispersity index, etc. The topical gel formulations were evaluated for pH, in vitro drug release, viscosity, in vivo performance and compared with the marketed formulation. The average size of prepared nanosponge formulations was found in the range of 102.8 nm to 475.5 nm. Scanning electron microscopy photographs of developed formulations reveal the spongy and porous nature of particles along with spherical shape. The polydispersity index (PI) was found in the range of 0.756 to 0.954. It was found that formulation F3 with a drug-to-polymer ratio of 1:3 has the highest drug loading. Further nanosponges were characterized for different parameters and results revealed acceptable characteristics of B3 formulation. These prepared nanosponges were loaded in topical Carbopol gel (Formulation AB3) and evaluated for in vitro and in vivo performance. The data were fitted to different kinetic models which reveal typical zero order in vitro drug diffusion with prolonged drug release. The developed formulation generated better analgesic and anti-inflammatory responses compared to the standard marketed formulation. [ABSTRACT FROM AUTHOR]

In order to improve and replace the enantiomer method outlined in the olodaterol hydrochloride draft monograph (From the European Pharmacopoeia forum), one new, simple, and fast enantioselective normal phase high‐performance liquid chromatography chiral method was developed on polysaccharide‐based Chiral MX (2) (4.6 × 250 mm, 5 μm) column. n‐Hexane, ethanol, and diethylamine in the ratio of 40:60:0.1 (V/V/V) were selected as mobile phase at a flow rate of 0.8 mL/min, and the detection was performed on a photodiode array detector at 225 nm with 5 μL injection volume. The column temperature was set at 40°C for better peak shape and sensitivity. The analysis time can be shortened to 15 min, whereas the resolution between enantiomer and olodaterol was found to be even more than 10.0, which was far better than that obtained with the reported method in this draft monograph. The developed chiral method was validated in accordance with ICH Q2 (R1), including specificity, LOD&LOQ, precision, linearity, accuracy, and robustness. Thereby, the proposed method was demonstrated to be suitable for the determination of enantiomer in olodaterol hydrochloride bulk drug and drug product. Besides, the thermodynamic parameters were evaluated on the basis of Van't Hoff plots that was used to explain correlative chiral recognition mechanisms with the chiral stationary phase. [ABSTRACT FROM AUTHOR]

An RP-HPLC method with a UV detector was developed for the simultaneous quantification of diclofenac diethylamine, methyl salicylate, and capsaicin in a pharmaceutical formulation and rabbit skin samples. The separation was achieved using a Thermo Scientific ACCLAIMTM 120 C18 column (Waltham, MA, USA, 4.6 mm × 150 mm, 5 µm). The optimized elution phase consisted of deionized water adjusted to pH = 3 using phosphoric acid mixed with acetonitrile in a 35:65% (v/v) ratio with isocratic elution. The flow rate was set at 0.7 mL/min, and the detection was performed at 205 nm and 25 °C. The method exhibits good linearity for capsaicin (0.05–70.0 µg/mL), methyl salicylate (0.05–100.0 µg/mL), and diclofenac diethylamine (0.05–100.0 µg/mL), with low LOD values (0.0249, 0.0271, and 0.0038 for capsaicin, methyl salicylate, and diclofenac diethylamine, respectively). The RSD% values were below 3.0%, indicating good precision. The overall greenness score of the method was 0.61, reflecting its environmentally friendly nature. The developed RP-HPLC method was successfully applied to analyze Omni Hot Gel® pharmaceutical formulation and rabbit skin permeation samples. [ABSTRACT FROM AUTHOR]

Experiments were carried out to transfer diethylamine (DEA) from water to carbon tetrachloride under static conditions inside a 50 cm3 buret for the fixed initial concentration of 2.5 mol dm−3. Initial concentration was chosen after ruling out lower concentrations to study the long-term instability. The phase volumes (i.e., 5 and 10 cm3) were equal for the separate trials at different extraction times. During extraction, intermittent interfacial jerking occurred up to 1800 s. After this time, the jerking frequency decreased and disappeared by 3600 s. The jerking time interval increased as the extraction progressed. Jerking resulted in profuse streaming into the extract phase, coupled with a throw of liquid from the interfacial region to the bulk of the aqueous phase. The complete concentration profiles of the solute in both phases were developed immediately after the jerking phenomena. In the aqueous phase, the concentration profiles revealed one and two zones of the minimum concentration of DEA in the bulk of the 5- and 10-cm3 phase volumes, respectively. The interfacial mass transfer coefficient during the jerking was high due to the absence of any interfacial barrier. The interfacial mass transfer coefficient in the absence of instability was much less than that in the presence of jerking. Also, it was higher than that for the systems where unidirectional ejections occurred due to the energy instability of the liquid–liquid interface. This work has also estimated the average spreading velocity of the interface, which caused the jerking due to the obstruction from the wall. [ABSTRACT FROM AUTHOR]

Emulsions stabilized by solid particles are called Pickering emulsions, using diclofenac diethylamine for topical use. In this study, screening for the effect of the type of solid particles (bentonite 3%; Avicel RC-591 2.5%; and kaolin 15%) and soybean oil concentration (10%; 20%, and 30%) using the Taguchi orthogonal array method, with independent variables (type of solid particles and concentration of soybean oil, dependent variables (viscosity, pH, %EE, creaming index, globule size, and % cumulative penetration). The Pickering emulsion with Avicel RC-591 for solid particles produced a stable emulsion during 21 days of storage. Using the Taguchi orthogonal array method, the best formula based on the dependent variable is Formula 4 with physical test results at viscosity 566 cp, pH value 8.18, adsorption efficiency 55.70%, creaming index 100%, globule size 57.1 µm, cell diffusion Franz test at 120 minutes resulted in a cumulative penetration of 69.829%. The penetration power of Formula 4 is better than the emulsion with tween and span emulsifiers, which has a cumulative amount at 120 minutes of 12.609%. Therefore, Avicel RC-591 2.5% solid particles with 10% soybean oil concentration resulted in a stable Pickering emulsion and better penetration than emulsions with tween and span emulsifiers. [ABSTRACT FROM AUTHOR]

Prodrugs are an important strategy for the development and design of therapeutic drugs. They involve the addition of an easily removable group (such as an ester) to a molecule in order to chemically protect it from metabolism, hydrolysis, or interaction with tissues. In the therapeutic drug market, prodrugs may reduce adverse effects, lead to more accurate tissue delivery, increase bioavailability and duration of effects. The same strategy has, however, been used in the illicit drug market. Internationally controlled drugs such as LSD, MDMA and benzodiazepines have been detected in the market with the addition of alkyl chain that can be removed in physiological conditions. Cyclical analogues may also be used, as is the case for 1cP‐LSD and GBL (a prodrug of GHB). Adequate detection requires increased care with extraction and analytical conditions—as the parent drugs may be formed as artifacts during these processes—and an in‐depth knowledge of metabolic pathways to avoid erroneous detection and allow for adequate identification of the drug used. Legislative updates may also be necessary to ensure prodrugs can be controlled at the same level as other illicit drugs. This article is categorized under:Toxicology > New Psychoactive SubstancesToxicology > Drug AnalysisToxicology > Analytical [ABSTRACT FROM AUTHOR]

Reactions between octa(2,6-fluorophenyl)porphyrazine and pyridine, 2-methylpyridine, morpholine, piperidine, butylamine, tert-butylamine, diethylamine, and triethylamine in a benzene medium have been studied. The acid–base reactions between the macroheterocycle and piperidine or butylamine are slow processes leading to the formation of kinetically stable proton-transfer complexes. The structures of these complexes have been optimized using CAM-B3LYP/cc-pVTZ. The changes in the reactivity of octa(2,6-fluorophenyl)porphyrazine are analyzed as a function of the steric structure and proton-acceptor power of the nitrogenous base. [ABSTRACT FROM AUTHOR]

A sensitive, easy-to-use, fast, and cost-effective TLC-densitometric method was developed for the separation of metronidazole, secnidazole, ornidazole, tinidazole, and 2-methyl-5-nitroimidazole and for the determination of metronidazole and tinidazole in Metronidazole Polpharma and Tinidazolum Polpharma tablets. Analyses were performed on chromatographic plates precoated with silica gel 60F254 using chloroform + methanol + diethylamine in a volume ratio of 9:1:1 as the optimal mobile phase. The method has been validated. The intraday and interday precision values for the three different concentrations ranged from 0.99% to 1.48% and 0.89% to 1.76%, and the precision values ranged from 1.13% to 2.48% and 0.95% to 2.49% for metronidazole and tinidazole, respectively. The limit of quantification (LOQ) was 0.036 and 0.066 µg/spot for metronidazole and tinidazole, respectively. The mean recovery was 103.1% and 100.6% for metronidazole and tinidazole, respectively. The content of metronidazole and tinidazole in tablets in relation to the content declared by the manufacturer was 101.3% and 99.8%, respectively. The obtained results were verified using the pharmacopeial method. The presented method is fast, sensitive, precise, selective, accurate, and robust. It allows for the analysis of several samples on one chromatography plate at the same time. [ABSTRACT FROM AUTHOR]

The title compound, (C4H12N)[V(C12H8N4O2)O2]H2O, was synthesized via aerial oxidation on refluxing picolinohydrazide with ethyl picolinate followed by addition of VIVO(acac)2 and diethylamine in methanol. It crystallizes in the triclinic crystal system in space group P.... In the complex anion, the dioxido-vanadium(V) moiety exhibits a distorted square-pyramidal geometry. In the crystal, extensive hydrogen bonding links the water molecule to two complex anions and one diethylammonium ion. One of the CH2 groups in the diethyl-amine is disordered over two sets of sites in a 0.7:0.3 ratio. [ABSTRACT FROM AUTHOR]

A tandem aldol condensation/Diels‐Alder sequence of reactions was designed leading to the synthesis of a new series of derivatives of polysubstituted‐decalines. Both steps of the process took place in the same pot and in the presence of H2O/PEG as the medium and diethylamine as the catalyst of the process. The required dienes were formed in situ and reacted with the dienophile (acrylonitrile) to produce high yields of the final decaline derivatives. Mechanistic studies suggested that the process goes through an initial aldol condensation reaction followed by a [4+2] cycloaddition step and then an olefinic bond rearrangement to give the final adducts. To support the proposed mechanism, the intermediate dienes were synthesized separately as well and their stepwise reactions with the dienophile led to the same products. Ten derivatives of the target structure were prepared and then characterized by various spectroscopic methods and X‐ray crystallography analysis. The procedure was also developed to engage some other dienophiles successfully. [ABSTRACT FROM AUTHOR]

A mechanism is proposed for the decomposition of molecular clusters of diethylamine (C2H5)2NH on the surface of the NaAux intermetallic compound with the formation of decomposition products desorbed from the surface, including in the form of ions with m/z from 58 to 197, during heating of the intermetallic compound at a rate of 20 K/s. Exposure of the NaAux surface at a temperature of 320 K in diethylamine vapor leads to the formation of molecular clusters on it. Rapid heating of NaAux at a rate of 20 K/s leads to the decay of clusters, desorption, and ionization of the decay products due to the redistribution of internal energy over the degrees of freedom of the cluster. The study of thermal ionization processes during heating of NaAux at a rate of 20 K/s in the temperature range from 600 to 1000 K made it possible to establish that the surface stoichiometry during heating is quasi-stationary, dehydrogenation and ionization of individual diethylamine molecules occur under equilibrium conditions, while for compounds formed in the process of cluster decay, the conditions are not equilibrium. [ABSTRACT FROM AUTHOR]

Background: Monitoring impurities in drug products is a principal requirement of pharmaceutical regulatory authorities all over the world to ensure drug safety. For this reason, there is a great need for analytical QC of dugs products. Objective: In this study, a simple, efficient, and direct HPLC method was developed for the determination of three impurities of diclofenac. Methods: The HPLC method was developed using a mobile phase which consisted of an HPLC grade mixture, acetonitrile-0.01M phosphoric acid adjusted to pH 2.3 (1 þ 3, by volume). Results: The separation was performed in 15 min. The calibration curves of the three impurities were linear; the correlation coefficients were 0.999 at concentrations of 0.00015-0.003 mg/mL. Conclusion: The validation of this method shows that it meets all validation criteria. This shows the reliability of this method for the routine control of diclofenac impurities. Highlights: The validation of a robust HPLC method for the determination of diclofenac impurities is of great importance for the pharmaceutical industry to control its products. [ABSTRACT FROM AUTHOR]

3-chloro-4-hydroxyphenylacetic acid (CHPAA) is a fungal metabolite. It is a small molecule that is useful in crystal engineering studies due to the functional groups present. Six amines were selected to form salts with CHPAA. Linear derivatives included diethylamine (DEA) and di-N-butylamine (DBM). The aromatic compounds chosen were 2-aminopyridine (A2MP), 2-amino-4-methylpyridine (A24MP), 2-amino-6-methylpyridine (A26MP) and 4-dimethylaminopyridine (DMAP). The salts were characterised using single-crystal X-ray diffraction, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. For all the crystal structures, N-H···O and C-H···Cl contacts were present. O-H···O contacts were found in all the crystal structures except for ( C H P A A 2 −) 2 D E A + , which was also the only structure that displayed a Cl···Cl contact. Furthermore, C-H···O contacts were found in all the crystal structures except for (C H P A A −) (D B M +).   The thermal stability trend showed that the DBM salt was more stable than the DEA salt. For the aromatic co-formers, the thermal stability trend showed the following: C H P A A − (D M A P +)   >   (C H P A A −) (A 2 M P +) > 2 C H P A A − 2 A 26 M P + > (C H P A A −) (A 24 M P +) . [ABSTRACT FROM AUTHOR]

Background. The creation of new effective corrosion inhibitors for structural grades of carbon steel is an urgent problem. In the area of achieving import substitution of this type of metal protection products, certain results have been achieved. Purpose. Creation and study of the properties of new inhibitors based on sodium carboxymethylcellulose and phosphorus-containing compounds. Methodology. Electrochemical (Corrtest: Potentiostat/Galvanostat), gravimetric, IR spectroscopic (IR spectrometer EN 1407) and X-ray phase (DRON-05) methods were used. Originality. For the first time, phosphorus-containing derivatives of sodium carboxymethylcellulose, diethylamine and aniline were used to create inhibitors, and a mechanism for their protective action was proposed. Findings. Sodium carboxymethylcellulose and phosphorus-containing corrosion inhibitors were synthesized and their properties were studied by physicochemical methods. [ABSTRACT FROM AUTHOR]

Diethylamine vapor is harmful to people if inhaled or swallowed, as it results in the oxidation of hemoglobin in the body into unwanted methemoglobin, which is unable to transport oxygen in the blood, resulting in reduced blood oxygenation. Lack of blood oxygenation leads to hypoxemia. MnO2 nanorods, carbon soot, and MnO2@ZIF-8 are sensing materials used to prepare solid-state gas sensors that operate at room temperature. The prepared sensing materials were characterized by scanning electron microscopy, transmission electron microscopy, powder X-ray diffraction, X-ray photoelectron spectroscopy, and Fourier-transform infrared spectroscopy. The performance of the MnO2@ZIF-8 based sensor improved significantly when the carbon soot was introduced into the composite. The effect of the amount of CNPs in the composite on the performance of the sensors was studied. The MnO2@ZIF-8/CNPs-based sensor with a 3:1 mass ratio was highly selective towards diethylamine vapor over acetone, methanol, ethanol, and 3-pentanone vapors. An in situ FTIR coupled with LCR meter was used to understand the sensing mechanism of diethylamine vapor and it was found that the sensing mechanism was by deep oxidation of diethylamine to CO2, H2O, and other molecules. The sensing mechanism was studied by monitored by CO2 band intensity which was produced from the reaction between the sensing materials and the analyte vapor. As the sensor's exposure time increased the intensity of the CO2 IR band increased. We observed the direct relationship between the surface reaction rate and the sensor's sensitivity.

New hydroxy-methylenebisphosphonic derivatives were prepared with different P-functions. The outcome of the reaction of α-oxophosphonates (YC(O)P(O)(OR)2) and dialkyl phosphites or diarylphosphine oxides depended on the Y substituent of the oxo-compound, the nature of the P-reagent and the amount of the diethylamine catalyst. Starting from dimethyl α-oxoethylphosphonate, in the presence of 5% of diethylamine, the corresponding Pudovik adduct was the single product. While using 40% of the catalyst, the rearranged species with the >P(O)–O–CH–P(O)< skeleton was the exclusive component. A similar reaction of α-oxobenzylphosphonate followed the rearrangement protocol. X-ray crystallography revealed not only the spatial structures of the three products, but also an intricate pattern evolving from the interplay of slight chemical differences, solvent inclusion and disorder as well as H-bridge patterns, which invite further investigation. In vitro activity of the compounds was assessed on different tumor cell cultures using end-point-type cell tetrazolium-based measurements. These structure–activity studies revealed a cytostatic effect for four rearranged derivatives containing aromatic units. One of them had a pronounced effect on MDA-MB 231 and Ebc-1 cells, showing IC50 = 37.8 and 25.9 µM, respectively. [ABSTRACT FROM AUTHOR]

We described here a simple and metal‐free protocol to synthesize [1,2,3]triazolo[1,5‐a]quinoline 3‐carboxamides through a two‐step synthetic strategy, in which the first step uses organocatalysis (10 mol % of diethylamine or 1,8‐diazabicyclo[5.4.0]undec‐7‐ene, while the second step involves the use of inorganic base (1.2 or 0.1 equiv. of potassium hydroxide). These reactions were performed between β‐keto amides and o‐carbonyl phenylazides in dimethylsulfoxide as solvent at 70 °C for 2 h. The synthetic protocol is ample, which thirteen examples of secondary [1,2,3]triazolo[1,5‐a]quinoline 3‐carboxamides were synthesized ranging from good to excellent yields (63‐96 %), and six different tertiary [1,2,3]triazolo[1,5‐a]quinolines 3‐carboxamides were obtained ranging from moderate to good yields (48–76 %). [ABSTRACT FROM AUTHOR]

Trimethylsilyl esters of P(III) acids were synthesized in high yields (89–94%) by the reaction of hydrophosphoryl compounds with hexamethyldisilazane at 20°C in the presence of ZnSO4 and diethylamine. The reaction is complete in 4 h, it does not require specially prepared solvents or an inert atmosphere, and can be proposed as a new synthetically useful and easy-to-perform method for the synthesis of trimethylsilyl esters of P(III) acids. [ABSTRACT FROM AUTHOR]

The removal yield of organic substances present in water depends on the environmental conditions, on the chemical composition of the water and on the chemical substance dissolved in the water, which constitutes the substrate of the metabolic activities of the microalgae that use these substances in the biochemical reactions of cellular enzyme complexes. o-Chlorobenzylidene malononitrile (CS, to use its military designation) was synthesized in-house, for research purposes, by a condensing reaction between o-chlorobenzaldehide and malononitrilein the presence of diethylamine. The detection, identification and confirmation of o-chlorobenzylidenemalononitrile (coded CBM in this experimental study) was performed using gas chromatography–mass spectrometry (GC-MS) and the purity of CBM was 99%. The biodegradation capacity in the samples that contained the biological suspension, after 24 h and 96 h of incubation, was determined via GC-MS analysis, and no evidence of the presence of CBM or some metabolites of CBM was detected. In the parallel samples, a hydrolysis process of CBM at room temperature, without biological treatment, revealed two main metabolites, malononitrile and o-chlorobenzaldehyde, respectively. This study is focused on evaluating the biodegradation capacity of o-chlorobenzylidene malononitrile in the presence of a biological material, culture of Chlorella sp., in comparison with a classical hydrolysis process. The tests performed indicate that the suspension of Chlorella sp. consumed the entire amount of CBM and metabolites from the analyzed samples. The tests prove that the biological material can be used to decontaminate the affected areas. [ABSTRACT FROM AUTHOR]

Hydrogen gas production generated from carbon-free molecules while utilizing solar energy provided a pathway for zero carbon emission energy. In photocatalytic hydrogen gas production, alcohol and oxygenated compounds as sacrificial agents are often added to accelerate the water splitting process while simultaneously decomposing to form H2 and CO2. However, the generation of CO2 requires an additional measure to curb carbon from being released into the atmosphere. This study evaluated the performance of TiO2 photocatalysts to generate hydrogen from NH3 solution as carbon-free molecules. The investigation is extended to alkylamines compounds as sacrificial agents. H2 is linearly produced from NH3 when using Pd/TiO2; however, the rate is reduced after a prolonged photocatalytic reaction. Alkylamines molecules are more susceptible for H2 production than NH3, with the reactivity increased from NH3 < triethylamine < diethylamine < ethylamine. Comparative analysis was also conducted on the amount of H2 and CO2 gases released from alkylamines and alcohols to indicate nitrogen-containing compounds viability as sacrificial agents for carbon-emission free sacrificial agents in photocatalytic water splitting reaction. [ABSTRACT FROM AUTHOR]

New N-substituted oxime derivatives (5b, 5d-g, 5i-k, and 5m) and known compounds (5a, 5c, 5h, 5g, 5l, and 5n-q) were obtained by reacting phenyl and butyl oxime chloride analogs with aniline, piperazine derivatives, piperidine, and diethylamine. Structures of all new compounds were determined by 1H NMR, 13C NMR, HRMS, and FTIR methods. All compounds were evaluated in vitro for their antiradical activity and hydrogen peroxide scavenging activity. Compounds 5g, 5h, 5i, 5j, 5k, 5l, 5m, and 5p have shown good antiradical activities with EC50 values < 1 (conc. antiradical (µM)/conc. DPPH (µM)). Similar results were obtained in the peroxide scavenging activity tests. These results have shown that piperidine and butyl substitution greatly increases the antiradical activity of the oximes. Compounds 5l and 5m were found to be the best radical scavengers. In addition, molecular docking studies were performed for compounds (5a-q) against CP450 (CYP1A2), NADPH oxidase, and Xanthine oxidase to predict their antioxidant capabilities through ROS-producing enzyme inhibitions. [ABSTRACT FROM AUTHOR]

Background: The objective of this current study was to fabricate and characterize the sustained release double layered transdermal patches of Diclofenac Diethylamine using hydrophobic acrylic polymer Eudragit RL 100 and hydrophilic polymer Polyvinyl pyrrolidone K-30 in combination as first layer of matrix type patch and pressure sensitive acrylic adhesive Duro Tak 387-2510 as the second layer of drug-in-adhesive type patch to provide sustained anti-inflammatory effect. Materials and Methods: Solvent casting method was employed to prepare patch over the backing membrane. The double layered technique were attempted to create the desirable features of acrylic polymer and adhesive. The drug-polymers compatibility studies were examined by Infrared spectroscopy. A full-thickness excised abdominal rat skin sample was used to perform the permeation studies using Franz's Diffusion Cell. Results: Drug-polymers compatibility studies revealed no evidence of interaction and the formulations showed satisfactory physicochemical-mechanical characteristics. It was found that release profiles were affected by the proportion of polymer and permeation enhancer used. The optimized formulation MF3 showed maximum in vitro and ex vivo percent cumulative drug permeated i.e. 87.28 ± 3.88% and 81.95 ± 2.64% respectively, with flux 12.96 ± 0.51 μg/cm2/h and permeability coefficient 1.09 ± 0.45 cm/h, in 24 hr. Also, the permeation studies suggested that dimethyl sulphoxide exhibit more promising results as permeation enhancer. Conclusion: It was concluded that an ideal Diclofenac Diethylamine double layered transdermal patch would serve as the best carrier to provide sustained effect with desirable permeation enhancement characteristics. [ABSTRACT FROM AUTHOR]

Purpose: Knee osteoarthritis (KOA) is regarded as one of the leading musculoskeletal diseases. Although the efficacy is under exploration, fire needling therapy is considered an effective alternative for KOA. This trial aims to investigate the effectiveness of different frequencies of fire needling therapy in attenuating pain and promoting function in KOA patients. Methods: This is a study protocol for a pilot, three-arm, single-center, randomized controlled trial. A total of 90 participants with KOA will be recruited and randomly assigned to the high-frequency fire needling group (3 sessions per week, for 6 weeks), the low-frequency fire needling group (1 session per week, for 6 weeks) or the positive control group (Diclofenac Diethylamine Emulgel, 3 times per day, for 6 weeks) in a 1:1:1 ratio. Participants will accomplish the trial at Week 14 after a follow-up evaluation. The response rate will be set as the primary outcome that the proportion of participants obtaining a minimal clinically important difference, which is identified as ≥ 2 units on the numerical rating scale (NRS) and ≥ 6 units on the Western Ontario and McMaster Universities Osteoarthritis Index (WOMAC) function score at Week 6 compared with Week 0. Secondary outcomes are NRS, WOMAC, Brief Pain Inventory, Short-Form Health Survey-12, Timed Up and Go Test, and pain threshold. Discussion: This is the first standardized protocol comparing fire needling therapy and positive control drugs. This trial may provide reliable evidence for the effectiveness of fire needling therapy and dose–effect property of it in KOA. Trial registration: The trial has been registered on Chinese Clinical Trial Registry (Registered number: ChiCTR2100043041), registered on 4 February 2021. [ABSTRACT FROM AUTHOR]

Resins have enormous potential in the removal of naphthenic acids (NAs) from transformer oil due to their rich porosity and high mechanical and diversified functionality, whereas their poor adsorption capacity limits application. In this work, the polystyrene–diethylamine resin (PS−DEA−x) was prepared by grafting diethylamine (DEA) onto chloromethylated polystyrene (PS−Cl) resin to efficiently adsorb cyclopentane carboxylic acid from transformer oil for the first time. The characterization analysis results indicated that amine contents were significantly enhanced with the increase in DEA. Particularly, resin with a molar ratio of 1:5 depending on chloromethyl to DEA (PS−DEA−5) exhibited the highest amine contents and efficient adsorption of cyclopentane carboxylic acid (static adsorption capacity up to 110.0 mg/g), which was about 5 times higher than that of the pristine PS−Cl. The thermodynamic and kinetic studies showed that the adsorption behaviors could be well fitted to the Langmuir isotherm equation and pseudo−second−order rate equation. Moreover, it was found that 1 g of the PS−DEA−5 can decontaminate about 760 mL transformer oil to meet reuse standards by a continuous stream, indicating its potential application in industry. [ABSTRACT FROM AUTHOR]

This work presents the development and optimization of the stability-indicating method for solifenacin succinate and its main degradation product, formed through oxidation, using the high-performance liquid chromatography technique with diode array detection using the quality by design approach. In this work, a forced degradation study was performed to evaluate the potential degradation profile of the active ingredient, solifenacin succinate. Here, multiple optimizations of the extraction procedure are proposed. Often, the prescribed procedure focuses on recovering the active pharmacological ingredient while neglecting the recovery of impurities, a critical step in the development of stability-indicating methods. In this step, an experimental design of mixtures using the simplex model was used in order to optimize the recovery of the active ingredient and its main degradation product. Mixture solvents were evaluated by combining water (0–40%), acetonitrile (0–100%), and ethanol (0–100%) using the ultrasound-assisted extraction technique, with evaluation times set at 10 and 30 min. The highest values were obtained using a solvent mixture of acetonitrile and ethanol in a ratio of 90 : 10 (v/v), along with a 30-minute ultrasound-assisted extraction. These recovery values exceeded those of the control condition. The development of the chromatographic method was carried out from a screening step based on the conditions reported in the literature. Subsequently, it was submitted to an optimization step where the possible analysis time was significantly reduced without loss of chromatographic efficiency. The optimal condition obtained was on the Xbridge chromatographic column with dimensions of 250 × 4.6 mm and 5 μm particle size. The system operated in gradient mode using a mobile phase containing a phosphate buffer (pH 6.7), with 0.5% diethylamine and acetonitrile in a ratio of 85 : 15 (v/v). Another mobile phase contained a phosphate buffer (pH 6.7) with 0.5% diethylamine and acetonitrile in a ratio of 20 : 80 (v/v). The temperature of the chromatographic column was maintained at 40°C, with a mobile phase flow rate of 1.1 mL/min and an injection volume of 10 μL in a gradient elution mode. The developed method was applied to evaluate the degradation profile of commercially purchased drugs. [ABSTRACT FROM AUTHOR]

Background: Diclofenac diethylamine (DDEA) gel has demonstrated efficacy for treatment of ankle sprains in both the 1.16% four-times-daily (QID) and 2.32% twice-daily (BID) formulations. The objective of this study was to compare, for the first time, the efficacy of DDEA 2.32% gel BID and DDEA 1.16% gel QID. Methods: This was a phase 3, randomized, double-blind, multicenter, active-controlled, parallel-group study conducted in China from October 2019 to November 2020, designed to determine the noninferiority of DDEA 2.32% gel BID relative to DDEA 1.16% gel QID for treatment of grade I–II ankle sprain. At study entry, patients must have had pain on movement (POM) ≥50 mm on a 100-mm visual analogue scale (VAS), and not received any pain medication. The primary efficacy endpoint was the noninferiority of DDEA 2.32% gel BID vs DDEA 1.16% gel QID for POM as assessed by the patient using the 100-mm VAS, conducted on day 5. Secondary endpoints included measures of ankle tenderness, joint function, swelling, and patient-reported pain intensity and pain relief. Results: A total of 302 patients were randomized and 95.4% completed the study. The mean (SD) change in POM from baseline to day 5 using the 100-mm VAS was − 42.8 mm (19.7 mm) with DDEA 2.32% gel BID and − 43.1 mm (18.1 mm) with DDEA 1.16% gel QID for the per-protocol population. The least squares mean difference (DDEA gel 2.32% – DDEA gel 1.16%) at this timepoint was 1.11 mm (95% CI − 3.00, 5.22; P = 0.595), and the upper limit (5.22 mm) of the 95% CI was less than the noninferiority margin of 13 mm, demonstrating that DDEA 2.32% gel BID was noninferior to DDEA 1.16% gel QID. Similar trends were seen for the secondary efficacy endpoints. There was no significant difference in the incidence of treatment-emergent adverse events or adverse events adjudicated as being treatment related. All treatment-related adverse events were dermatological; one patient discontinued from the DDEA 2.32% gel BID arm due to application-site inflammation. Conclusions: DDEA 2.32% gel BID offers a convenient alternative to DDEA 1.16% gel QID, with similar pain reduction and relief, anti-inflammatory effects, and tolerability. Trial registration: NCT04052620. [ABSTRACT FROM AUTHOR]

3-chloro-4-hydroxyphenylacetic acid (CHPAA) is a fungal metabolite. It is a small molecule that is useful in crystal engineering studies due to the functional groups present. Six amines were selected to form salts with CHPAA. Linear derivatives included diethylamine (DEA) and di-N-butylamine (DBM). The aromatic compounds chosen were 2-aminopyridine (A2MP), 2-amino-4-methylpyridine (A24MP), 2-amino-6-methylpyridine (A26MP) and 4-dimethylaminopyridine (DMAP). The salts were characterised using single-crystal X-ray diffraction, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. For all the crystal structures, N-H···O and C-H···Cl contacts were present. O-H···O contacts were found in all the crystal structures except for (CHPAA2−)2DEA+, which was also the only structure that displayed a Cl···Cl contact. Furthermore, C-H···O contacts were found in all the crystal structures except for (CHPAA−)(DBM+). The thermal stability trend showed that the DBM salt was more stable than the DEA salt. For the aromatic co-formers, the thermal stability trend showed the following: CHPAA−(DMAP+) > (CHPAA−)(A2MP+)>2CHPAA−2A26MP+>(CHPAA−)(A24MP+).

New bis(N,N-diethylamino)(phenethyl)methylsilane and 1,2-bis(N,N-diethylamino)-1,2-di(phenethyl)-1,2-dimethyldisilane were synthesized by the reaction of diethylamine with (phenethyl)methyldichlorosilane. Structure of the obtained compounds was confirmed by 1Н, 13С, and 29Si NMR spectroscopy data. [ABSTRACT FROM AUTHOR]

The existence of heavy metals such as Cr(VI) in water is a threat to human and animal life. Herein, a novel method is reported, whereby, a low-cost adsorbent was prepared by reacting the cellulose ofMoringa Oleifera leaves with epichlorohydrin and triethylamine using diethylamine (DEA) as a modifying agent for Cr(VI) and bacterial removal. The functionalised Moringa Oleifera(FMO) was confirmed using XRD, FTIR, TGA, SEM, BET and Zeta potential. The FTIR results showed that the amino groups were successfully grafted on the surface of Moringa Oleifera (MO). Dosage, pH, contact time and initial concentrations were optimised to 2.5 g, 2, 85 min and 20 mg/L, respectively. The FMO removed 99% Cr(VI) at optimum conditions. Adsorption kinetics fitted well with pseudo second order, suggesting a chemisorption mechanism between Functionalisedcellulose ofMoringa Oleifera(FMO) and Cr(VI). The maximum adsorption capacity obtained from Langmuir Isotherm for Cr(VI) removal was 60.6061 mg/g. The correlation coefficient (R2) obtained from the linear calibration curve of Cr(VI) was 0.9999, with a limit of quantification (LOQ) and limit of detection (LOD) of 1.486 and 0.4461 mg/L, respectively. Reusability studies also displayed that the material could be used for up to 7 cycles, with a > 90% Cr (IV) removal. This bio adsorbent was highly selective towards chromium(VI) in the industrial waste water containing interfering ions. FMO was also tested for its antibacterial activity using pond, river, tap and sewage water against several bacterial strains. It was found that the FMO was most potent against E. coli, Staphylococcus aureus and total coliforms. Based on the data obtained, this study has shown that environmentally safe bioadsorbents can be used as multifunctional materials for the treatment of water. [ABSTRACT FROM AUTHOR]

We have developed novel series of 5-arylidene-1, 3-thiazolidin-4-one analogues using diethylamine as catalyst. Diethylamine was found suitable in synthesizing variety of title compounds in 62-85% yield. In-vitro anticancer activity of synthesized analogues was evaluated using human breast (MCF7), lung (Hop62) and hepatic (HepG2) cell lines using SRB assay. Amongst the synthesized compounds 9b, 9e, 9f are excellent in inhibiting growth of cancer cell lines with GI50 value <10µg/ml in comparison with Adriamycin standard. We have also performed docking studies using SHP2 in complex with inhibitor (PDB ID: 2Shp) but results were non-supportive, very weak. We found no correlation between anticancer studies and docking studies. [ABSTRACT FROM AUTHOR]

Amines with two carbon atoms in the organic chain [ethylamine (EA), diethylamine (DEA), triethylamine (TEA)] have been used as precipitant agents to obtain a hydrotalcite-like compound with Zn (II) and Al (III) as layered cations and with nitrate anions in the interlayered region to balance the charge. This Layered Double Hydroxide was prepared following the coprecipitation method, and the effect on the crystal and particle sizes was studied. Also, the effect of submitting the obtained solids to hydrothermal post-synthesis treatment by conventional heating and microwave assisted heating were studied. The obtained solids were exhaustively characterized using several instrumental techniques, such as X-ray diffraction, Thermal Analysis (DTA and TG), Chemical Analysis, Infrared Spectroscopy (FT-IR), determination of Particle Size Distribution and BET-Surface area. Well crystallized solids were obtained showing two possible LDH phases, depending on the orientation of the interlayer anion with respect to the brucite-like layers. The results indicated that there is a certain influence of the amine, when used as a precipitating agent, and as a consequence of the degree of substitution, on the crystallinity and particle size of the final solid obtained. The LDHs obtained using TEA exhibited higher crystallinity, which was improved after a long hydrothermal treatment by conventional heating. Regarding the shape of the particles, the formation of aggregates in the former solid was detected, which could be easily disintegrated using ultrasound treatments, producing solid powder with high crystallinity and small particle size, with homogeneous size distribution. [ABSTRACT FROM AUTHOR]

The study investigated the effects of the concentration of secondary amines with various molecular weights (specifically, diethylamine, di-n-propylamine, diisopropylamine, and di-n-butylamine), which were used as templates, on the crystallization performance of AlPO4-11 molecular sieves. For this purpose, various analytical methods such as XRD, SEM, and N2 adsorption/desorption were employed. The template concentration (more specifically, the template/Al2O3 ratio) was shown to have a major effect on the phase composition of the crystallization products. However, for each template under study, a high-phase-purity AlPO4-11 could be synthesized only within a narrow range of template/Al2O3 ratios. The study demonstrated the effects of template type on the morphology and dispersion of AlPO4-11 molecular sieves. [ABSTRACT FROM AUTHOR]

The hydroaminomethylation of the long-chain olefin 1-decene and diethylamine with a homogeneous Rh(acac)(cod)/SulfoXantphos catalyst complex as a one-pot synthesis was investigated. The influence of reaction conditions such as temperature and synthesis gas pressure was determined, as well as the effects of the initial concentrations of catalyst precursor, ligand, and reactants on the yield of fatty amine. Hydroaminomethylation was successfully carried out in an aqueous microemulsion system using a non-ionic surfactant with a reaction time of 2 h. A maximum yield of 34%, high regioselectivities >97%, and chemoselectivities >85% were achieved. [ABSTRACT FROM AUTHOR]

Many amines with high toxicity always cause a serious threat to the ecological environment and human health; thus, their detection is important. Herein, a dual-mode colorimetric and ratiometric fluorescent sensor based on cellulose for detecting amines has been constructed by a new strategy. This sensor is made of a "negative response" indicator (Lum-MDI-CA) and a "positive response" indicator (perylene tetracarboxylic acid, PTCA). Lum-MDI-CA was obtained by attaching luminol onto cellulose chains, which emitted blue fluorescence and was quenched upon contact with amines. A possible mechanism of fluorescence quenching phenomenon is proposed by the intramolecular charge transfer (ICT) of Lum-MDI-CA. Subsequently, by simply mixing Lum-MDI-CA with PTCA, a dual-mode fluorescence sensor was designed for visual detection and classification of amines. When adding ammonia (NH 3), morpholine (MOR), benzylamine (BNZ), diethylamine (DEA), and triethylamine (TEA), respectively, the dual-mode sensor showed visible different color changes under both UV light and daylight. In addition, owing to the excellent processibility and formability of cellulose acetate backbone, the prepared sensor can be easily processed into different material forms, including inks, coatings, films, and fibers, which still exhibit excellent fluorescence emission. Such sensors based on cellulose fluorescent materials are of great value in anti-counterfeiting and information encryption. [Display omitted] [ABSTRACT FROM AUTHOR]

[Display omitted] • Two-step dehydrogenation reaction of DEA to generate acetonitrile and ethylene occurred on Cu 5 /TiO 2. • DEA could directly decompose into ethylamine and ethylene on Cu 5 /HZSM-5(27). • Severe coke deposition was formed on Cu 5 /HZSM-5(27) with strong Brønsted acidity. • Cu 5 /HZSM-5(130) and Cu 5 /S-1 with lower Brønsted acidity and reducibility released more unwanted gas-phase byproducts. This work investigated the reaction behaviors of diethylamine (DEA) catalytic oxidation on various Cu-based catalysts with different supports (TiO 2 , HZSM-5(27), HZSM-5(130) and S-1). It was found that the acidic environment of catalysts greatly influenced reaction pathways of DEA oxidation. On Cu 5 /TiO 2 catalyst mainly with Lewis acidity, DEA preferentially dissociated through a two-step dehydrogenation to produce acetonitrile and ethylene, while on Cu 5 /HZSM-5(27) catalyst with strong Brønsted acidity, DEA could directly decompose into ethylamine and ethylene via N-C cleavage. Both pathways existed simultaneously over Cu 5 /HZSM-5(130) with decreased Brønsted acidity. Thereafter, acetonitrile could be further oxidized on the Cu 5 /TiO 2 catalyst to generate a large amount of NO x via NCO(a) intermediates over-oxidation, while ethylamine on Cu 5 /HZSM-5 samples would convert to acetamide and then produced N 2 and CO 2. The Cu2+ species due to enriched Brønsted acid sites in Cu 5 /HZSM-5 catalysts ensured excellent N 2 selectivity via internal SCR mechanism. Additionally, the strong Brønsted acidity of Cu 5 /HZSM-5(27) could induce the polymerization of carbonaceous intermediates and thereby resulted in severe coke deposition. As for Cu 5 /HZSM-5(130) and Cu 5 /S-1 with relatively lower Brønsted acidity and reducibility would release some unwanted gas-phase by-products like ethyl-isocyanate. This work provided useful guidance for designing NVOCs catalysts with high activity and less toxic by-products. [ABSTRACT FROM AUTHOR]

Resins have enormous potential in the removal of naphthenic acids (NAs) from transformer oil due to their rich porosity and high mechanical and diversified functionality, whereas their poor adsorption capacity limits application. In this work, the polystyrene–diethylamine resin (PS−DEA−x) was prepared by grafting diethylamine (DEA) onto chloromethylated polystyrene (PS−Cl) resin to efficiently adsorb cyclopentane carboxylic acid from transformer oil for the first time. The characterization analysis results indicated that amine contents were significantly enhanced with the increase in DEA. Particularly, resin with a molar ratio of 1:5 depending on chloromethyl to DEA (PS−DEA−5) exhibited the highest amine contents and efficient adsorption of cyclopentane carboxylic acid (static adsorption capacity up to 110.0 mg/g), which was about 5 times higher than that of the pristine PS−Cl. The thermodynamic and kinetic studies showed that the adsorption behaviors could be well fitted to the Langmuir isotherm equation and pseudo−second−order rate equation. Moreover, it was found that 1 g of the PS−DEA−5 can decontaminate about 760 mL transformer oil to meet reuse standards by a continuous stream, indicating its potential application in industry.

An automated sorbentless cryogenic needle trap device (ASCNTD) was developed for the extraction of organic volatile impurities (OVIs) from solid pharmaceuticals prior to their determination by gas chromatography (GC). In this method, a new set up was designed and used to extraction of several OVIs from ceftazidime, ceftriaxone sodium and amoxicillin. For this purpose, a proper amount of the sample was transferred into the extraction vessel. The sample headspace components were started to circulate through a needle with a flow rate of 20 mL min−1. The OVIs were trapped on the inner surface of a needle placed on top of the sample by flowing liquid nitrogen. After a predetermined time, the coiled nichrome resistance wire placed into the hollow ceramic rod was heated and the trapped analytes were desorbed and swept into the GC capillary column using the carrier gas. The effective parameters such as volume of the sample vial, headspace flow rate, extraction temperature and time, and desorption conditions have been investigated. Qualification studies reveal that pyridine (as a degradation product of ceftazidime), methylene chloride, diethylamine, triethylamine, isopropyl alcohol and n -butyl acetate are the main impurities in the studied pharmaceuticals. Detected OVIs were quantitated using external standard method. The obtained relative standard deviation values were <8%, and the limits of detection (LOD) for the detected OVIs were in the range of 1–34 ng g−1. [ABSTRACT FROM AUTHOR]

Vortioxetine (VOR) is a new antidepressant drug used to treat major depressive disorder. In this work, a novel, simple, rapid, accurate, precise, selective, stability-indicating, and fully validated high-performance liquid chromatography method with diode array detection (HPLC-DAD) was developed to determine VOR in bulk and pharmaceutical formulations. A Polar-RP column was used, with a mobile phase consisting of acetonitrile (ACN), methanol (MeOH), acetate buffer pH 3.5, and addition of diethylamine (DEA) in the isocratic elution mode. Assessing the stability of the VOR is fundamental to guarantee the efficacy, safety, and quality of drug products. In this study, the VOR active pharmaceutical ingredient (API) and tablets were subjected to a detailed study of forced degradation, using several degrading agents (acid, alkaline, water, heat, light, and oxidation agents). The developed HPLC-DAD method allows the collection of all the essential data to determine degradation kinetics. It was found that the decomposition of vortioxetine is fragile towards oxidative conditions and photolysis, yielding the first-order and second-order kinetic reaction in the above stress conditions, respectively. The degradation products (DPs) were identified by the high-resolution liquid chromatography coupled with electrospray ionization-quadrupole-time of flight-mass spectrometry (LC-ESI-QTOF-MS) method. The HPLC-DAD method was successfully applied for the quantification of VOR in tablets. Additionally, in silico toxicity prediction of the DPs was performed. [ABSTRACT FROM AUTHOR]

Chlorination disinfection byproducts (CDBPs) can exert adverse human health effects. Many toxicology-based studies confirmed the health hazards of CDBPs, but little research has been done on gut microbiome. We explored the effect of CDBPs on intestinal microbiota in the Simulator of the Human Intestinal Microbial Ecosystem (SHIME). The results showed that CDBPs slightly inhibited the production of short-chain fatty acids, and the abundance of Actinobacteria decreased in the transverse colon and descending colon. The abundance of Proteobacteria increased in the ascending colon and descending colon, while it decreased in the transverse colon. The abundance of Firmicutes decreased in both the ascending colon and descending colon. In particular, the abundance of Lachnospiraceae members, Bilophila, Oscillospira, Parabacteroides, Desulfovibrio, and Roseburia increased in the ascending colon, while the abundance of Sutterella, Bacteroides, Escherichia, Phascolarctobacterium, Clostridium, Citrobacter, and Klebsiella increased in the descending colon. The Shannon index differed significantly in both the ascending colon and descending colon before and after exposure. Overall, we demonstrate the feasibility of applying the SHIME model to studying the effects of intestinal toxicity on health of chlorinated by-products. The findings of this study improve our understanding of the health impact of CDBPs on the intestinal microbiota and better control of CDBPs in treated water is recommended. [ABSTRACT FROM AUTHOR]

This paper presents the results of selective purification of oil distillates with a viscosity of 7.5 mm2/s and 18 mm2/s at 1 0 0 ∘ C, as well as a mixture of these oil distillates obtained by compounding at various ratios using an ionic liquid based on diethylamine and formic acid as an extractant acid. The conditions for the ionic liquid dearomatization of the indicated oil distillates were determined by studying the influence of various factors on the selective purification process. Many parameters are set for the objects of research. The values of physicochemical parameters determined under various conditions are presented in the tables. [ABSTRACT FROM AUTHOR]

Two mononuclear protic ferrocenyl acyclic diamino carbene gold(I) complexes AuCl[C(NHFc)(NR2)] were prepared by nucleophilic attack of diethylamine (R = Et) and diisopropylamine (R = iPr) at the ferrocenyl substituted isocyanide complex chlorido(isocyanoferrocene)gold(I) AuCl(CN−Fc). In the solid state, the multifunctional protic carbene gold(I) complexes display intermolecular aurophilic interactions or intermolecular NH⋅⋅⋅Cl hydrogen bonding in addition to intramolecular non‐classical NH⋅⋅⋅Fe hydrogen bonds. Oxidation of the AuCl[C(NHFc)(NR2)] complexes initially takes place at the iron centres giving highly coloured ferrocenium ions, which subsequently likely undergo electron transfer from gold(I) to iron(III) yielding putative EPR‐active gold(II) species. [ABSTRACT FROM AUTHOR]

Rationale: The mass spectra of amine thermal ionization on intermetallic NaAux emitters differ significantly from those of the same compounds on the surfaces of transition metals and their oxides. The factors underlying these differences are determined through studying the processes taking place on intermetallic surfaces, which give rise to the corresponding mass spectra. Methods: The dependence of mass spectral composition and individual line intensity of diethylamine thermal ionization on intermetallic NaAux surface on diethylamine pressure, oxygen, sodium atom current and emitter temperature was studied using a magnet sector mass spectrometer. Results: Diethylamine mass spectral composition is determined by the reaction between the molecules adsorbed on the NaAux surface. Oxygen and sodium concentration on the surface does not affect the mass spectral composition. Mass line intensity depends on diethylamine pressure and emitter temperature affecting the reaction efficiency on the surface. Conclusions: Intermetallic NaAux is an ionic semiconductor that can provide sufficient lifetime for adsorbed molecules to efficiently interact with each other and with their decomposition products. This creates unique conditions for the formation of various compounds on the surface with their mass exceeding by 2.5 times that of diethylamine. [ABSTRACT FROM AUTHOR]

The structure of the title compound, C27H46N2, at 93K has monoclinic (P21/n) symmetry. The title compound was prepared by treatment of 2-(2,6-diisopropylphenyl)-3,3-dimethyl-2-azaspiro[4.5]dec-1-en-2-ium hydrogen dichloride with two equivalents of lithium diethylamide. Characterization of the title compound by single-crystal X-ray diffraction and ¹H and 13C NMR spectroscopy is presented. Formation of the diethylamine adduct of the cyclic(alkyl)(amino)carbene (CAAC) was unexpected, as deprotonation using lithium diisopropylamide results in free CAAC formation. [ABSTRACT FROM AUTHOR]