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Results for “BARBITAL DERIVATIVES”

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At least 19 recordsLinked to original sources
PubMed1987

A barbital derivative as an atypical antidepressant drug in mice.

An isopropyl derivative of barbital (5,5-diethyl-2-(isopropyloxy)pyrimidine-4,6-dione, O2IB) was administered intraperitoneally 30 min before tests in mice. Former experimental investigations have shown that O2IB has an antidepressant psychopharmacological spectrum. It increases toxicity of yohimbine in mice at 175 mg/kg, antagonises from 50 mg/kg on hypothermia induced by a high dose of apomorphine and is active on the behavioural despair test at 125 mg/kg. These effects are those observed with classical antidepressants. Since phenytoin has an antidepressant profile in mice, carbamazepine is active on manic-depressive illness and beta-mimetic drugs are antidepressants, the question presents itself whether isopropylation or anticonvulsive activity is more important for the antidepressant psychopharmacological spectrum, or whether both are of equal importance.

Animals↗
PubMed1985

Heteroassociation of O- and N-isopropyl derivatives of barbital and phenobarbital with 9-ethyladenine.

Heteroassociation of O- and N-isopropyl derivatives of barbital and phenobarbital with 9-ethyladenine (9-EA) in CCl4 solutions were studied by infrared spectroscopy. Cyclic heterodimers of high stability (725 less than KH less than 1960 1 X mol-1) compared to the corresponding homodimers (20 less than KD less than 60 1 X mol-1) were formed. The heteroassociation constants are interpreted in terms of both the hydrogen bonding tendency of the donor and acceptor centres and the number of sites available for the formation of hydrogen bonds. Such measurements may contribute to the understanding of the interactions between barbiturates, adenosine and their receptors in the brain.

Adenine↗
PubMed1989

Synthesis of N-beta-D-glucopyranosyl derivatives of barbital, phenobarbital, metharbital, and mephobarbital.

The condensation of per(trimethyl)silylbarbital and -phenobarbital with 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose in the presence of stannic chloride in dichloroethane gave moderate yields of the beta-coupled barbiturate N-D-glucopyranosyl derivatives. Reaction of metharbital and mephobarbital under the same conditions was unsuccessful. The homologous N-methylglucosides were prepared by reaction of the barbital and phenobarbital N-glucosyl derivatives with diazomethane. The diastereomers of the phenobarbital and mephobarbital derivatives were resolved by use of C-18 reverse-phase h.p.l.c. 1H- and 13C-n.m.r. spectroscopy, and thermospray 1.c.-m.s. proved to be the most useful methods for characterizing the barbiturate glucosides.

Barbital↗
PubMed1995

Synthesis of N-beta-D-glucopyranosyluronate derivatives of barbital, phenobarbital, metharbital, and mephobarbital.

The synthesis and characterization of barbital, phenobarbital, metharbital, and mephobarbital glucuronides is reported. The condensation of per(trimethylsilyl)-barbital and -phenobarbital with methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate in the presence of trimethylsilyl trifluoromethanesulfonate gave moderate yields of the N1-(beta-D-glucopyranosyluronate) barbiturate derivatives. The diastereomers of the phenobarbital derivatives were resolved by use of C18 reversed-phase HPLC. The homologous N3-methyl barbiturate N1-glucuronates were prepared by reaction of the barbital and phenobarbital N1-glucuronate derivatives with diazomethane. The absolute configuration of the phenobarbital N1-beta-D-glucopyranuronate epimers was determined by oxidative removal of the glycon from the mephobarbital N1-beta-D-glucopyranuronate epimers to give the optical isomers of mephobarbital. The spectroscopic data for this series of compounds will facilitate the characterization of N-glycosylated imide xenobiotics that may be detected as mammalian metabolites in biodisposition studies.

Barbital↗
PubMed1989

Ion-pair HPLC study of sulfonamides, barbiturates and antiphlogistic acids on a dynamically modified silica gel stationary phase.

The behaviour of some groups of acidic drugs (barbital derivatives, sulfonamides and antiphlogistic acids) was studied with a reversed-phase ion-pair HPLC method. A methanol-water-posphate buffered (pH = 7) mobile phase containing various concentrations of cetrimide was applied on a silica gel column. The correlations between the migration and the chemical structure within the different groups of compounds are discussed. Monofunctional benzene derivatives were utilized to investigate the influence of the various functional groups in this system on the retention.

Anti-Inflammatory Agents↗
PubMed1986

Central effects of N-allyl,N'-methyl-barbital and N-allylmethyprylon in mice.

Pharmacological activities (hypnotic, anticonvulsant and convulsant activities, acute toxicity and pentobarbital (PB) synergism) of N-allyl,N'-methyl derivatives of barbiturates and related N-allyl substituted compounds were studied in mice. N-Allylhexobarbital (AHB), N-allylglutethimide (AGI) and N-allylmethyprylon (AMP) showed hypnotic activity. N-Allyl,N'-methyl derivatives of barbital (B), phenobarbital (PheB) and PB (AMB, AMPheB and AMPB), AHB and AMP exhibited anticonvulsant activity against pentylenetetrazol (PTZ)-induced seizures. AMP was the most potent agent among the allyl compounds tested in the protective effect against PTZ-induced seizures. N-Allyl, N'-methylallobarbital (AMAlloB) showed a weak convulsant activity at a dose of 640 mg/kg, i.p. All allyl compounds tested showed potentiation of the PB-induced sleep. AMB prolonged the PB-induced sleep 30-fold as compared with the control. These results indicate that AMB, AMP and the other N-allyl compounds possess some depressant effects on the central nervous system.

Allyl Compounds↗
PubMed1986

N,N'-diallylbarbital potentiation of drug-induced sleep and motor incoordination.

Pharmacological activities (hypnotic activity, anticonvulsant activity against pentylenetetrazol (PTZ)-induced seizures and motor incoordination) of N-allyl substituted derivatives of barbital (B) were investigated using mice. N-Monoallylbarbital (MAB) was found to possess more potent hypnotic activity [HD50 = 146(140-152)mg/kg, i.p.] and anticonvulsant activity [PTZ-ED50 = 25.1(18.1-34.8)mg/kg, i.p.] than the parent compound, barbital [HD50 = 179(153-209)mg/kg, i.p. and PTZ-ED50 = 27.7(25.5-30.1)mg/kg, i.p.]. N,N'-Diallylbarbital (DAB) was devoid of not only the hypnotic activity, but also of anticonvulsant activity and motor incoordination. The interactions of these N-allyl derivatives with various sedative-hypnotics [B, phenobarbital (PheB), amobarbital (AB), pentobarbital (PB), thiopental (TP) or diazepam (DZ)] were studied to characterize the antagonist or agonist properties of these N-allyl compounds. MAB (50-200 mg/kg, i.p.) showed a dose-dependent potentiation of B (200 mg/kg, i.p.)-induced sleep. DAB (150-300 mg/kg, i.p.) prolonged B-induced sleeping time, but its dose-response relationship was not clearly observed. Both compounds (150 mg/kg, i.p.) also significantly prolonged PheB-, AB-, PB- and TP-induced sleeping time. Further, DAB (40 mg/kg, i.p.) enhanced DZ-induced motor incoordination. These results indicate that MAB and DAB potentiate sedative-hypnotics responses in different manner, and that the mechanism of action may be due to their different effect, each other, on the central nervous system (CNS).

Animals↗
PubMed1986

Isopropyl substitution on barbiturate ring: effects on 'open field' and 'hole board' behaviour and on biogenic amines concentrations in discrete regions of the rat brain after acute and chronic administration.

Previous studies have shown that slight modification of the barbitone molecule can lead to enhanced sedative activity, convulsant activity or putative antidepressant activity according to the position of the isopropyl substituent on the N- or O-moiety. When the acute effects of the N-, O2- and O4-isopropyl derivatives of barbital (NIB, O2IB), O4IB on the concentrations of brain biogenic amines were determined, it was found that NIB and O4IB increased the serotonin concentrations in several brain regions examined without markedly changing the 5-hydroxy-indole acetic acid (5-HIAA) concentrations; in contrast, O2IB increased the 5-HIAA concentration. Barbitone and NIB raised the concentration of noradrenaline in two of the regions examined whereas the O2-substituted derivative had a smaller effect; the dopamine concentration was slightly raised by NIB and O2IB. Following their chronic (14 days) administration, only barbitone and O2IB raised the serotonin concentration; O2IB raised the concentration of 5-HIAA in some regions as did NIB, which suggests that these compounds may increase serotonin turnover. Barbitone and O2IB slightly increased the noradrenaline content of the brain stem while only O2IB decreased the dopamine content. These results suggest that the effects of acute and chronic administration of barbitone and its isopropyl derivatives are qualitatively different; their effects are less marked after chronic administration. The GABA concentration was only affected after chronic administration, when NIB was shown to increase and O2IB to decrease the concentration. Following their chronic administration, O2IB decreased while NIB increased the locomotor activity of rats in the 'open field' and 'hole board' apparatus.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2000

Recovery of sodium dodecyl sulfate-proteins from gel electrophoretic bands in a single electroelution step for mass spectrometric analysis.

Mass spectrometric analysis of proteins derived from bands in gel electrophoresis is incompatible with the covalent fluorescent labeling of the protein. Thus, if one wishes to take advantage of the capacity for computer-directed electroelution of electrophoresis apparatus with intermittent fluorescent scanning of the migration path, the protein must be labeled fluorescently in a noncovalent, reversible fashion. This was recently achieved by staining of SDS-proteins with Cascade blue and electrophoresis in barbital buffer. However, the method was not a practical one for the purpose of isolating proteins from gel electrophoretic bands and their transfer into the mass spectrometer for three reasons: (i) Ten consecutive electroelution steps were required to obviate pH changes in the electroelution chamber; (ii) electroeluates from six gel electrophoretic lanes needed to be pooled; (iii) excessive protein loads ranging from 7 to 33 microg/pool were required. The present study reports the solution to those three problems. Mass spectrometric (MALDI-TOF) characterization of five proteins was demonstrated (i) after a single electroelution step; (ii) using electroelution from a single gel of 0.3-cm(2) cross-sectional area; and (iii) using a protein load of 2 (in one case 4) microg. However, the migration rates of the Cascade blue-SDS-protein-barbital complexes derived from proteins with widely varying molecular weights proved to be the same. Thus, despite the three advances made, the method to date remains restricted to samples of single proteins.

Electrophoresis, Agar Gel↗