Determination of low concentrations of dibenzylamine in human plasma and urine by gas chromatography with a nitrogen-phosphorus detector

Calvo, M.B.; Pedraz, J L; Domínguez-Gil, A

doi:10.1016/s0378-4347(00)82776-0

Cited by 6 publications

(4 citation statements)

References 4 publications

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“…N ‐(phenylmethyl)‐benzenemethanamine, also called dibenzylamine, a thermal decomposition product of the vulcanization agent zinc dibenzyldithiocarbamate and a possible precursor to the formation of N ‐nitrosodibenzylamine,40 was discovered in four out of ten ethyl acetate extracts. Dibenzylamine has also been found by other authors in artificial saliva leachates from baby bottle teats40 and in human‐plasma and urine samples 41. Fig.…”

Section: Resultssupporting

confidence: 56%

Searching for anthropogenic contaminants in human breast adipose tissues using gas chromatography‐time‐of‐flight mass spectrometry

et al. 2008

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The potential of GC-TOF MS for screening anthropogenic organic contaminants in human breast adipose tissues has been investigated. Initially a target screening was performed for a list of 125 compounds which included persistent halogen pollutants (OC pesticides, PCBs, PBDEs), PAHs, alkylphenols, and a notable number of pesticides from the different fungicide, herbicide and insecticide families. Searching for target pollutants was done by evaluating the presence of up to five representative ions for every analyte, all measured at accurate mass (20 mDa mass window). The experimental ion abundance ratios were then compared to those of reference standards for confirmation. Sample treatment consisted of an extraction with hexane and subsequent normal-phase HPLC or SPE clean-up. The fat-free LC fractions were then investigated by GC-TOF MS.Full-spectral acquisition and accurate mass data generated by GC-TOF MS also allowed the investigation of non-target compounds using appropriate processing software to manage MS data. Identification was initially based on library fit using commercial nominal mass libraries.This was followed by comparing the experimental accurate masses of the most relevant ions with the theoretical exact masses with calculations made using the elemental composition calculator included in the software.The application of both target and non-target approaches to around 40 real samples allowed the detection and confirmation of several target pollutants including p,p'-DDE, HCB, and some PCBs and PAHs. Several non-target compounds that could be considered anthropogenic pollutants were also detected. These included 3,5-di-tert-butyl-4-hydroxy-toluene (BHT) and its metabolite 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO), dibenzylamine, n-butyl benzenesulfonamide, some naphthalene-related compounds and several PCBs isomers not 3 included in the target list. As some of the compounds detected are xenoestrogens the methodology developed in this paper could be useful in human breast cancer research.4

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Section: Resultssupporting

confidence: 56%

Searching for anthropogenic contaminants in human breast adipose tissues using gas chromatography‐time‐of‐flight mass spectrometry

et al. 2008

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“…Finally it should be noticed that the lowest effective concentration in the present study of 5 µmol/l DBA is not far away from the maximum plasma concentration of 0.72±0.15 µmol/l (141.6±28.7 ng/ml) determined when applying the antibiotic cephazoline-dibenzylamine at a dose of 1250 mg (Calvo et al 1989). One should therefore be aware that DBA could exert subtle changes of cardiac, or possibly also other voltage-dependent K + currents.…”

Section: Discussioncontrasting

confidence: 50%

“…the pungent irritant capsaicin (Castle 1992), the local anaesthetics bupivacaine (Castle 1990) and quinidine (Jahnel et al 1994), the Ca 2+ channel blockers verapamil and nifedipine (Jahnel et al 1994), and the K + channel blocker tedisamil (Dukes and Morad 1989). In this study, we describe the block of the voltage-dependent K + current by dibenzylamine (DBA), a compound that has been introduced into certain antibiotics, as cephazoline, to generate a sustained pharmacological action of these antibiotics (Calvo et al 1989). After release from the complex in the organism, DBA behaves as an independent chemical entity.…”

Section: Introductionmentioning

confidence: 99%

Dibenzylamine - a novel blocker of the voltage-dependent K + current in myocardial mouse cells

Doepner

Koopmann

Knopp

et al. 2001

Naunyn-Schmiedeberg's Archives of Pharmacology

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Ventricular myocytes of the mouse ventricle were voltage clamped with a patch-clamp technique in the whole-cell configuration. At depolarizing voltage pulses, these myocytes develop a large voltage-dependent K+ outward current. Application of the drug dibenzylamine (DBA) to the bath solution blocked the voltage-dependent K+ current. The concentration/response relationship for the peak current at +40 mV indicates a 1:1 binding of the drug to the receptor with a concentration of half maximum effect of 43.1 micromol/l. The block did not require activation of the channels by depolarizing pulses. At concentrations causing partial block (25 micromol/l), the block was independent of voltage. At the same concentration, DBA completely blocked the slow component of the recovery from inactivation (-80 mV) whereas steady-state inactivation was not altered. It is concluded that DBA is a novel blocker of the voltage-dependent K+ current in mouse cardiac myocytes which preferentially affects the current component generating the slow recovery from inactivation.

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“…DBA is a benzaldehyde derivative whose clinical import stems from its use as a pharmacologic vehicle for certain antibiotics (26) and as a biologically active contaminant identified in commercial preparations of l ‐(+)‐β‐hydroxybutyrate (4,22). Although it is a novel compound with promising anticonvulsant properties, it is labeled as a toxic, potentially carcinogenic substance in the Environmental Protection Agency (EPA) inventory under the Toxic Substances Control Act (TSCA), and thus is a poor candidate for further preclinical and clinical development.…”

Section: Discussionmentioning

confidence: 99%

Voltage‐Dependent Block of N‐Methyl‐d‐Aspartate Receptors by the Novel Anticonvulsant Dibenzylamine, a Bioactive Constituent of l‐(+)‐β‐Hydroxybutyrate

et al. 2003

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Summary:Purpose: Previously we demonstrated that L-(+)-β-hydroxybutyrate (L-BHB), acetoacetate (ACA), acetone, and dibenzylamine (DBA) were anticonvulsant in an audiogenic seizure-susceptible model, and that DBA was a bioactive contaminant identified in commercial lots of L-BHB. In the present study, we asked whether these effects could be mediated by ionotropic glutamate or γ -aminobutyric acid A (GABA A ) receptors.Methods: We studied the effects of both stereoisomers of BHB (as well as the racemate), ACA, and DBA on N-methyl-Daspartate (NMDA), α-amino-3-hydroxy-5methyl-4-isoxazoleproprionic acid (AMPA), and GABA A receptors in cultured rodent neocortical neurons by using whole-cell voltage-clamp recording techniques.Results: Only L-BHB and DBA exerted a concentration-and voltage-dependent block of NMDA-evoked currents, whereas none of the tested substrates affected AMPA-or GABA-activated currents. The kinetics of whole-cell block by L-BHB and DBA were similar, providing additional evidence that DBA is responsible for the anticonvulsant activity of L-BHB.

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Determination of low concentrations of dibenzylamine in human plasma and urine by gas chromatography with a nitrogen-phosphorus detector

Cited by 6 publications

References 4 publications

Searching for anthropogenic contaminants in human breast adipose tissues using gas chromatography‐time‐of‐flight mass spectrometry

Searching for anthropogenic contaminants in human breast adipose tissues using gas chromatography‐time‐of‐flight mass spectrometry

Dibenzylamine - a novel blocker of the voltage-dependent K + current in myocardial mouse cells

Voltage‐Dependent Block of N‐Methyl‐d‐Aspartate Receptors by the Novel Anticonvulsant Dibenzylamine, a Bioactive Constituent of l‐(+)‐β‐Hydroxybutyrate

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