Schönenberger, Helmut and Brinkmann, R. and Bamann, E. (1964) Constitution and pharmacological activity of N-aminoacylephedrines, a new class of local anesthetics. Kongr. Pharm. Wiss., Vortr. Originalmitt., 23., Muenster, (Westfalen), Ger. 1963, pp. 361-367.
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Reaction of ephedrine or amphetamine with mixed anhydrides of dialkylamino acids and carboxylic acid half esters yields a novel series of acyl derivs. which have local anesthetic activity. Their mechanism of activity is discussed. The acyl derivs. synthesized [Arch. Pharm. 296(1), 33-7(1963)], e.g. N-(DL-N-dimethylphenylalanyl)-L-y-ephedrine, are sepd. into diastereoisomers by the Craig countercurrent method. By detailed sepn. and study of the constellations of the isomeric mols., using ir spectroscopy and dissocn. const. measurements, a relation between molecular shape and local anesthetic activity is tentatively established, provided the compd. is sufficiently sol. in the lipoid fraction, in dog corneas (Tammelin and Lofgren, CA 42, 7443i).
|Additional information (public):||CAN 62:44082 41 Alkaloids 1668-82-2; 2480-20-8; 5042-94-4; 7232-10-2; 7232-11-3; 7232-12-4; 7275-84-5; 7278-68-4; 10385-91-8 (Derived from data in the 7th Collective Formula Index (1962-1966); 299-42-3 (Ephedrine) (N-(aminoacyl) derivs., anesthetic activity of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Hydrocinnamamide (anesthetic activity of)|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||22 Nov 2010 13:58|
|Last Modified:||22 Nov 2010 13:58|