Chemical Constitution, Physiological Action and Physical Properties in a Series of Alkyl Para-Aminobenzoates

Abstract

The alkyl esters of p-aminobenzoic acid, because of their insolubility in water, cannot be employed for anesthetic purposes in aqueous solution, and the corresponding salts, though soluble, are far too acid in character to be used. The bases have, therefore, found their chief application as dusting powders. Numerous attempts have been made to correlate chemical constitution and physiological action of members of this series but there seems to be very little agreement among different investigators even where similar methods of testing were used; moreover, each previous worker has dealt with only a few members of the series. No attempt has been made to correlate physical properties and physiological action of these compounds.This investigation involved the preparation and study of various alkyl ^-aminobenzoates, namely, methyl, ethyl, propyl, isopropyl, n-, iso-, sec.-and tert.-butyl, «-amyl and allyl. The relative physiological action of these anesthetics on goldfish, the surface tension effects and the partition coefficients between amyl acetate and water have been determined and compared.Physiological Action.-Sturmer and Luders1 tested a few of these anesthetics on the mucous membrane of the mouth and found that the npropyl ester was strong, isopropyl weaker, isobutyl weaker and that the isoamyl was strong but irritating. They concluded that increase in molecular weight of the alcohol results in decrease of anesthetic value and increase in toxicity.

Correlation and Prediction of Mass Transport across Membranes I: Influence of Alkyl Chain Length on Flux-Determining Properties of Barrier and Diffusant

“…When these data were treated by Zahradnik (41) years later, a least-squares line was drawn through the points as they lay, giving a false impression of the magnitude of the index increase as a fuiiction of chain length. Other observations of Adams et al (38) are consistent with a transition to solubility limitations and diffusion layer control, particularly the trend in recovery time of the goldfish when returned to fresh water. These were of short duration (less than 5 min.)…”

Effects of Alkyl Chain Length on Biological Activity: Alkyl p - Aminobenzoate-Induced Narcosis in Goldfish

“…3 or 4 or from the data in the last column of Table 11. The best value of x appears to be 0.40, which is in good agreement with the value of 0.413 determined from the data of Adams et al (20) for the lower alkyl p-aminobenzoates. It is also in agreement with other data for goldfish (21, 22).…”

Comparison of Local Effects of Alpha Butyloxy-Cinchoninic Acid-Gamma Diethylethylenedi-Amide ("Nupercaine") With Cocaine and Procaine

“…We chose the rabbit cornea for topical measurements, and the wheal test for infiltration indices. We added a third test, recommended recently for determining anesthetic efficiency: the gold-fish method of Adams, et al (18), as modified by Dailey and Benedict (19). While these tests were being carried out, the drug was tried in about 285 cases in our surgical clinic.…”