Publications by authors named "Jack DeRuiter"

Background: Iatrogenesis is an inevitable global threat to healthcare that drastically increases morbidity and mortality. Cancer is a fatal pathological condition that affects people of different ages, sexes, and races around the world. In addition to the detrimental cancer pathology, one of the most common contraindications and challenges observed in cancer patients is severe adverse drug effects and hypersensitivity reactions induced by chemotherapy.

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Bisphenol-S (BPS) is a current substitute for Bisphenol-A (BPA) in various commercial products (paper, plastics, protective can-coatings, etc.) used by all age groups globally. The current literature indicates that a drastic surge in pro-oxidants, pro-apoptotic, and pro-inflammatory biomarkers in combination with diminished mitochondrial activity can potentially decrease hepatic function leading to morbidity and mortality.

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The goal of this study was to analyze the effect of COVID-19 drugs and biologicals on hyperglycemia. A literature search with key terms, such as "COVID-19 drugs and hyperglycemia" and "COVID-19 vaccines and hyperglycemia," was conducted using PubMed through September 2021. The CDC data were referenced for current COVID-19 profile and statistics.

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Background: COVID-19 and tuberculosis (TB) are infectious diseases that predominantly affect the respiratory system with common symptoms, such as cough, fever, and shortness of breath, making them dual burdens.

Methods: This review will discuss the characteristics of the coexistence of TB and new infectious illnesses to provide a framework for addressing the current epidemic. Currently, there are no clear and significant data on COVID-19 infection in TB patients, they may not respond appropriately to drug therapy and may have worse treatment outcomes, especially if their TB treatment is interrupted.

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Rationale: The halogenated derivatives of N-(2-methoxy)benzyl-2,5-dimethoxyphenethylamine (25-NBOMe) such as the 4-bromo analogue (25B-NBOMe) represent a new class of hallucinogenic or psychedelic drugs. The purpose of this study was to determine the role of the electron-donating groups (halogen and dimethoxy) in the pathway of decomposition for the distonic molecular radical cation in the electron ionization mass spectrometry (EI-MS) process of the trifluoroacetamide (TFA) derivatives.

Methods: The systematic removal of substituents from the 4-halogenated 2,5-dimethoxyphenethylamine portion of the N-dimethoxybenzyl NBOMe analogues allowed an evaluation of structural effects on the formation of major fragment ions in the EI-MS of the TFA derivatives.

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A series of N,N-disubstituted piperazines were synthesized containing the structural elements of both methylenedioxybenzylpiperazine (MDBP) and trifluoromethylphenylpiperazine (TFMPP) in a single molecule. These six potential designer drug molecules having a regioisomeric relationship were compared in gas chromatography-mass spectrometry (GC-MS), gas chromatography-infrared spectroscopy and serotonin receptor affinity studies. These compounds were separated by capillary gas chromatography on an Rxi®-17Sil MS stationary phase film and the elution order appears to be determined by the position of aromatic ring substitution.

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The analytical differentiation of the indole ring regioisomeric chloro-1- n-pentyl-3-(1-naphthoyl)-indoles is described in this report. The regioisomeric chloroindole precursor compounds, N- n-pentyl chloroindole synthetic intermediates, and the target chloro-substituted naphthoylindoles showed the equivalent gas chromatographic elution order based on the position of chlorine substitution on the indole ring. The regioisomeric chloro-1- n-pentyl-3-(1-naphthoyl)-indoles yield electron ionization mass spectra having equivalent major fragments resulting from cleavage of the groups attached to the central indole nucleus.

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Designer drugs are synthetically formulated to mimic the psychostimulatory effects of an original controlled/illegal drug of abuse. Designer drugs have similar chemical structure or functional analog as compared to existing controlled psychostimulatory drugs. There is a substantial rise in the production and use of designer drugs globally.

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Tuberculosis represents a significant public health crisis. There is an urgent need for novel molecular scaffolds against this pathogen. We screened a small library of marine-derived compounds against shikimate kinase from Mycobacterium tuberculosis ( MtSK), a promising target for antitubercular drug development.

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The indole ring regioisomeric methoxy-1-n-pentyl-3-(1-naphthoyl)-indoles represent indole ring-substituted analogs of the synthetic cannabinoid JWH-018. The electron ionization mass spectra show equivalent regioisomeric major fragments resulting from cleavage of the groups attached to the central indole nucleus. The characteristic (M-17)+ fragment ion at m/z 354 resulting from the loss of OH group is significant in the mass spectra of all four compounds.

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The twelve 1-n-pentyl-2-, 3-, 4-, 5-, 6- and 7-(1- and 2-naphthoyl)-indoles each have the same substituents attached to the indole ring, identical elemental composition (CHNO) yielding identical nominal and accurate masses. These twelve isomers cover all possible positions of carbonyl bridge substitution for both indole (positons 2-7) and naphthalene rings (positions 1 and 2). Regioisomeric compounds can represent significant challenges for mass based analytical methods however, infrared spectroscopy is a powerful tool for the identification of positional isomers in organic compounds.

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Article Synopsis
  • The study focuses on six regioisomers of 1-n-pentyl-2-, 3-, 4-, 5-, 6-, and 7-(2-naphthoyl)-indoles, all sharing the same substituents and elemental composition.
  • Electron ionization mass spectra show similarities and some differences in fragment ions among the isomers, indicating different cleavage patterns.
  • The separation of amide inverse isomers and their improved gas chromatography retention compared to naphthoyl ketone isomers reveals the influence of substituent placement on the indole ring.
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Benzylpiperazine has been designated as Schedule I substance under the Controlled Substances Act by Drug Enforcement Administration. Benzylpiperazine is a piperazine derivative, elevates both dopamine and serotonin extracellular levels producing stimulatory and hallucinogenic effects, respectively, similar to methylenedioxymethamphetamine (MDMA). However, the comparative neurotoxic effects of Piperazine derivatives (benzylpiperazine and benzoylpiperazine) have not been elucidated.

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Multiple and complementary analytical methods are often necessary for the identification of a specific compound from a series of closely related structural isomers. Gas chromatography-mass spectrometry (GC-MS), gas chromatography-product ion mass spectrometry (GC-MS/MS) and gas chromatography-infrared spectroscopy (GC-IR) were used to differentiate between the six dimethoxypyrrovalerone (DMPV) regioisomers. The six regioisomeric aminoketones were separated on a 50% phenyl stationary phase and the elution order is related to the positioning of substituents on the aromatic ring.

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The desoxy phenethylamine analogues in this study represent a combination of alkyl side-chain and cyclic amines (azetidine, pyrrolidine, piperidine and azepane) to yield a set of molecules of identical elemental composition as well as major mass spectral fragment ions (base peaks) of identical elemental composition. These desoxy phenethylamine analogues of the aminoketone designer drug, 3,4-methylenedioxy-pyrrovalerone (MDPV) related to the natural product cathinone were prepared from piperonal (3,4-methylenedioxybenzaldehyde) via the intermediate precursor ketones. The aminoketones and the desoxy phenethylamine regioisomers were each separated in capillary gas chromatography experiments using an Rxi-17Sil MS stationary phase with the aminoketones showing greater retention than the corresponding desoxyamines.

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A combination of GC-MS, MS/MS and GC-IR techniques were used to characterize the ring substitution pattern, the alkyl side-chain and the cyclic tertiary amine portions of a series of six homologous and regioisomeric methylenedioxyphenyl-aminoketones related to the designer drug, 3,4-methylenedioxypyrovalerone (MDPV). Chromatographic retention increases with the hydrocarbon content of the alkyl side-chain and the 3,4-methylenedioxy substitution pattern shows higher retention than the corresponding 2,3-methylenedioxy isomer. The aminoketones show major peaks in their mass spectra corresponding to the homologous series of iminium cation fragments from the loss of the regioisomeric methylenedioxybenzoyl radical species.

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Rationale: A number of synthetic cathinones (aminoketones, 'bath salts') are tertiary amines containing a cyclic amino group, most commonly pyrrolidine. These totally synthetic compounds can be prepared in a number of regioisomeric designer modifications and many of these can yield isomeric major fragment ions in electron ionization mass spectrometry (EI-MS).

Methods: A series of regioisomeric cyclic tertiary amines were prepared and evaluated in EI-MS and MS/MS product ion experiments.

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Rationale: Precursor materials are available to prepare aminoketone drugs containing regioisomeric propyl and isopropyl side-chain groups related to the drug alpha-pyrrovalerone (Flakka) and MDPV (3,4-methylenedioxypyrrovalerone). These compounds yield equivalent regioisomeric iminium cation base peaks in electron ionization mass spectrometry (EI-MS).

Methods: The propyl and isopropyl side-chain groups related to alpha-pyrrovalerone and MDPV were prepared and evaluated in EI-MS and tandem mass spectrometry (MS/MS) product ion experiments.

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The regioisomeric 1-n-pentyl-3-(methoxybenzoyl)indoles and the 1-n-pentyl-3-(methylbenzoyl)indoles represent potential designer modifications in the synthetic cannabinoid drug category. These six compounds were prepared by a two-step synthetic method. The analytical properties and methods of regioisomeric differentiation were developed in this study.

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Rationale: A number of synthetic cannabinoids such as the 1-alkyl-3-acylindoles are the target of significant designer drug activity. One of the first waves of these compounds identified in clandestine samples was 1-n-pentyl-3-(1-naphthoyl)indole, JWH-018. These totally synthetic molecules can be prepared in a number of regioisomeric forms.

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The GC-MS properties of the synthetic cannabinoid drug of abuse 3-(1-naphthoyl)-1-pentylindole (JWH-018) and all 5 of its' regioisomeric 1-naphthoyl substituted 1-n-pentylindoles are compared in this report. These compounds have the 1-naphthoyl-group attached at each of the possible substituent positions of the indole ring. The six compounds have the same elemental composition C24H23NO and the same substituents attached to the indole ring.

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A number of N-substituted piperazines have been described as drugs of abuse in recent years. This new drug category includes several series of aromatic ring substituted phenylpiperazines. The wide variety of available precursors makes regioisomerism a significant issue in these totally synthetic compounds.

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This report compares the GC-MS and FTIR properties of all 6 regioisomeric benzoyl substituted-1-n-pentylindoles. These compounds have the benzoyl-group attached at each of the possible ring substituent positions of the indole ring. The six compounds have the same elemental composition C20H21NO yielding identical nominal and exact masses.

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The birth of the twenty first century has provoked a substantial rise in the use of designer drugs, such as synthetic cathinones, because of a decrease in the availability and purity of other drugs of abuse. The khat plant or Catha edulis, contains cathinone, the parent compound. Synthetic cathinones are sold under the name "bath salts" as a ploy to circumvent legislation from banning their use.

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A series of seven regioisomeric bromodimethoxy benzyl piperazines including the designer benzylpiperazine (4-bromo-2,5-dimethoxybenzylpiperazine) were synthesized and their analytical profiles evaluated using GC-MS and FT-IR. The mass spectra for the seven regioisomeric bromodimethoxy benzyl piperazines are almost identical with only the two 2,3-dimethoxy isomers showing one unique major fragment ion at m/z 214/216. Thus, mass spectrometry alone does not provide for the confirmation of identity of any one of the seven compounds to the exclusion of the other isomers.

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