By E. J. Ariëns (Eds.)
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30 dynes/cm. Introduction of a small amount of monocetyl phosphate lowers this value to about 12 dynes/cm. A histamine solution introduced into this system is able to produce a further decrease to 2-3 dynes/cm. Addition of an antihistaminic to the system nullifies the drop in interfacial tension, and, depending on the amount applied, the tension may even rise beyond the original value of the chloroform-water system. However, the above procedure was unable to distinguish between diphenhydramine and its derivatives with either distinctly higher antihistamine activity such as 4-methyldiphenhydramine (150), or much lower levels of antihistamine activity, such as the 2ter/-butyl and the 2,2',6,6'-tetramethyl derivatives.
It may, therefore, be readily assumed that already beyond η = 3 the phenyl group no longer produces a measurable effect on the base strength. This applies, mutatis mutandis, to the substituents in the phenyl ring as well. Since in a diphenhydramine as much as four atoms are present between the phenyl rings and the Ν atom, one would expect such a 51 1. DIPHENHYDRAMINE DERIVATIVES structure to be free of any substitution effect on the base strength. Yet, substituents in the phenyl rings clearly have such an effect.
In the 1950s, the period preceding this modern approach, considerable effort had been made to find a parallel between the physicochemical properties of various sets of drugs and their biological properties without due regard for statistical significance. A similar situation existed in the case of the diphenhydramines. Thus, attempts were made to correlate antihistamine activity with the stability of the ether bond (77), with the pK value of the base function (140), and with the antagonism of the surface tension lowering caused by histamine in an interface between chloroform and cetyl phosphate 43 1.