Ueber alkylirte Derivate des Anilins

1. The excretion in the bile and urine of intraperitoneally injected (14)C-labelled monoquaternary ammonium or pyridinium cations was measured in bile-duct-cannulated rats (ten compounds) and in guinea pigs and rabbits (six compounds). 2. Seven of these, namely N-methylpyridinium, tetraethylammonium, trimethylphenylammonium, diethylmethylphenylammonium, methylphenyldipropylammonium, dibenzyldimethylammonium and tribenzylmethylammonium, were excreted largely unchanged in the bile and urine. 3. 3-Hydroxyphenyltrimethylammonium, 3-bromo-N-methylpyridinium and cetyltrimethylammonium were metabolized to an appreciable extent in the rat. 4. In intact rats intraperitoneally injected trimethylphenylammonium (mol.wt. 136) was excreted mainly in the urine, dibenzyldimethylammonium (mol.wt. 226) was excreted in roughly equal amounts in the urine and faeces, and tribenzylmethylammonium (mol.wt. 302) was excreted mainly in the faeces. The faecal excretion of these compounds corresponded to their biliary excretion in bile-duct-cannulated rats. About 3-4% of tribenzyl[(14)C]methylammonium was eliminated as (14)CO(2). 5. In rats the extent of biliary excretion of four cations with molecular weights in the range 94-164 was less than 10% of the dose, whereas that of five cations with molecular weights 173-302 was greater than 10%. These results and other data from the literature suggested that the molecular weight needed for the biliary excretion of such cations to an extent of 10% or more of the dose was about 200+/-50. Studies with six cations in guinea pigs and rabbits suggest that this value applies also to these species. 6. The results suggest that the threshold molecular weight for the appreciable (>10%) biliary excretion of monoquaternary cations is different from that for anions (Millburn et al., 1967a; Hirom et al., 1972b). With rats, guinea pigs and rabbits, no significant species difference was noted, whereas with anions there is a marked species difference.

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“…After cooling, ether was added and an oil separated, which formed crystals from dry acetone (cf. Claus & Howitz, 1884).…”

Section: Preparationsmentioning

confidence: 99%

Molecular weight as a factor in the excretion of monoquaternary ammonium cations in the bile of the rat, rabbit and guinea pig

Hughes

Millburn

Williams

1973

Biochemical Journal

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Zur Charakteristik stereoisomerer Ammoniumsalze

Wedekind¹

1899

Ber. Dtsch. Chem. Ges.

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Die Einwirkung von Bromcyan auf tertiäre Amine

Braun

1900

Ber. Dtsch. Chem. Ges.

148

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iri dem Satze zusammengefasst: >ICs s c h e i i i t s o r n i t fiir e i n n e g a t i v e s R a d i c a l c h a r a k t e r i s t i s c hj a fiir s e i n Z u s t a n d ek o m n i e n b e s t i m n i e n dz u s e i n , d a s s i n i l i m h o m o g e n e o d e r h e t e r o g e n e A t o m e i n e n g e r e r G r u p p i r u n g , z. B. d o p p e l t o d e r d r e i f a c h g e b u II d e n , v o r k o m rn e n. a.Dies Resultat ist geeignet, der neuen Theorie eine vie1 weitere Basis L U schaffeii, als sie bisher hesnss, und muss dazu auffordern, a l l e mehifach gebundenen Atomgruppen, z. R. auch . C H : N . u. A.im Sinue der Theorie zu prufen.Meine Gesetzmassigkeiten habe ich allerdings damals irn Sinne der alten Theorie abgeleitet, indessen mit nllem Vorbehalt, denn S. 672 heisst es bei deu Metallsalzen ausdriicklich, dass *die Frage, ob das Metall an Kohlenstoff oder Sauerstoff etc. gebunden iste, offen bleil)eii SOIL In einer irn August letzten j a h r e s erschienenen Untersuchung: BUeLer den Glutaconsaureester Icl), sind die Forrneln ebenfalls im Sinne beider Theorien gegeben.Ohne inich fiir die Alleinberechtiguag der einen oder anderen Theorie ,aussprecben zu wollen, miichte ich betonen, dass im Sinne der ron mir gegebenen Definition der negativen Gruppen die Thatsache, dass z. H. die Wasserstofatorne des Methylenchlorids und andere ahnliche Verbindungen nicht ))ersetzbara sind, eine natiirliche Erkliirung finden wiirde. J. v. Braun: Die Einwirkung vonBromcgan auf tertiare Amine. [l. Mittheilung.] [Mittheilung itus den1 Chemischen Institut der UniversitBt Gbttingen.] (Eingegangen am 10. April.) Wahrend das Verhalten tertiarer Amine gegen Halogenalkylverbindungen schon seit Iangerer Zeit eingeliend untersucht worden ist. scheint man iiber das Verhalten dieser Basen gegen Halogencyanverbindungen noch garnichts zu wissen. Nachdem ich mich durch einige Vorversnche von der ausserordentlichen Reactionsfiihigkeit der rerschiedensten Nitrilbasen gegeri Halogencyan iiberzeugt hatte, unter-1) Wiener Monatshefte 20, 539 (1899).

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Ueber alkylirte Derivate des Anilins

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Molecular weight as a factor in the excretion of monoquaternary ammonium cations in the bile of the rat, rabbit and guinea pig

Molecular weight as a factor in the excretion of monoquaternary ammonium cations in the bile of the rat, rabbit and guinea pig

Zur Charakteristik stereoisomerer Ammoniumsalze

Die Einwirkung von Bromcyan auf tertiäre Amine

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