Die qualitative Analyse von Barbitursäurederivaten durch Kernresonanzspektroskopie

A hydrogen-bonding interaction between phenobarbital or pentobarbital with phosphatidyicholine in chloroform is indicated by the effects of added phosphatidylcholine on the infrared and proton magnetic resonance spectra of these barbiturates. The nitrogenbound proton of the barbiturate and the orthophosphate moiety of the phosphatidylcholine molecule appear to be involved. The more pronounced effect with the two barbiturates occurs in the proton magnetic resonance spectra of phenobarbital with increased amounts of phosphatidylcholine. A plot of the chemical shift of phenobarbital N-H against the concentration of phosphatidylcholine is linear and gives an extrapolated shift of 260 Hz (2.6 ppm)at 350C for a phosphatidylcholine-phenobarbital ratio of unity, pure 1:1 complex. It is suggested that the general depressant nature of barbiturates may be accounted for by their association in a similar fashion with a number of other phosphate-containing molecules.The biochemical effects of barbiturates are extremely diverse and occur in several organisms and cultured tissues. However, the molecular basis of their pharmacological action remains unknown. Barbiturates are general depressants. In addition to their well-known sedative action in the central nervous system, they also exhibit other depressant effects in biological systems. These include reduction of oxygen consumption in mammalian tissues, and inhibition of respiration in cell-free preparations of liver and brain mitochondria (1). Thus, it is likely that one or more moieties in the barbiturate enables it to interact with various other species. Barbituric acid itself produces no anesthetic effect; it becomes physiologically important only when side chains are attached to the C-5 position (Fig. 1). The substitution of different alkyl groups in the C-5 position is known to affect the onset and duration of anesthesia (2). The specificity and necessity for the lipophilic side chains presumably arises because the barbiturates are active in nonpolar regions, i.e., membranes. Thus, the side chains play an important role in the interaction between the barbiturate and the lipid portion of the membrane. Furthermore, this association itself could alter the properties of the membrane.Barbiturates can interact with other molecules through hydrogen bonds involving the N-H protons and the carbonyl oxygens (3). A particularly strong interaction of this type has been noted between barbiturates and adenine derivatives (3). Membranes contain a sizable concentration of a moiety which, because of its ability to accept protons may hydrogen-bond well with the barbiturate N-H protons, namely, the ionized phosphates of phospholipids.We present here direct evidence for an association in vitro between phosphatidylcholine (PChol) and two different barbiturates, phenobarbital and pentobarbital, using nuclear magnetic resonance (NMR) and infrared spectroscopy as the analytical tools. MATERIALS AND METHODS3,-y-Dipalmitoyl-L-phosphatidylcholine (Sigma Chemical), and phenobarbital (Merck) ...

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“…The proton magnetic resonance (PMR) spectra characteristic of barbiturates have been described (4 Fig. 3.…”

Section: Resultsmentioning

confidence: 99%

Barbiturate Interaction with Phosphatidylcholine

Novak

Swift

1972

Proc. Natl. Acad. Sci. U.S.A.

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Die quantitative Bestimmung von Schlafmitteln mit Acetylen‐ und Piperidinstruktur durch Kernresonanzspektroskopie)

Rüċker

Natarajan

1967

Archiv der Pharmazie

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R ii e k er und N a t a r a j a n Archiv der Pharmazie Die Bildung der Diphenylathylendiamine aus Benzylidenalkylaminen und aktiviertern Aluminium wird von zahlreichen Faktoren in verschiedenartiger Weise beeinflufit, wie die Ausfuhrungen dieser und vergangener Arbeitenl) 2, 3, zeigen.Von wesentlicher Bedeutung fur die Entstehung der Dimerprodukte ist aber auch die Struktur der Schiffschen Base. Das Studium der Zusammenhange zwischen Aldiminstruktur und Dimerenausbeute ist. das Ziel unserer weiterenuntersuchungen.Der Deutschen Forschungsgemeinschaft und dem Fonds der Chemischen Industrie danken wir fur die Forderung unserer Untersuchungen.

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Arzneimittelanalyse durch Kernmagnetische Resonanz 3. Qualitative und quantitative Analyse von analgetisch wirkenden Kombinationspräparaten

Rehse

1970

Archiv der Pharmazie

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Die qualitative Analyse von Barbitursäurederivaten durch Kernresonanzspektroskopie

Cited by 15 publications

References 5 publications

Barbiturate Interaction with Phosphatidylcholine

Barbiturate Interaction with Phosphatidylcholine

Die quantitative Bestimmung von Schlafmitteln mit Acetylen‐ und Piperidinstruktur durch Kernresonanzspektroskopie)

Arzneimittelanalyse durch Kernmagnetische Resonanz 3. Qualitative und quantitative Analyse von analgetisch wirkenden Kombinationspräparaten

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