Syntheses in the epinephrine series / by Frank Tutin, Frederic W. Caton and Archie C.O. Hann.

  • Tutin, Frank.
Date:
[1909?]
Catalogue details

Licence: In copyright

Credit: Syntheses in the epinephrine series / by Frank Tutin, Frederic W. Caton and Archie C.O. Hann. Source: Wellcome Collection.

    3/18
    CCXXVII.—Syntheses in the Epinephrine Series. By Frank Tutin, Frederic William Caton, and Archie Cecil Osborn Hann. Inasmuch as the base epinephrine, which possesses a constitution represented by formula I (Jowett, Trans., 1904, 85, 192), has so valuable a physiological action, it appeared to be of considerable interest to prepare certain substances related to it, in order that their properties might be physiologically investigated: HO hq/ •CH(OH)-CH2-NH*CH3 (I.) It is already known that the ketone corresponding with epinephrine is physiologically active, as are also the primary amines (II and III) corresponding with both these compounds: HO •CH(OH)*CH2-NH2 (II.) HO HO<^ \cOCH2-NH (HI.) We therefore endeavoured to prepare bases analogous to the above-mentioned primary amines, but which would contain only one hydroxyl group in the benzene nucleus. This attempt has been successful, in so far as the para-derivatives are concerned, for £-p-dihydroxy-$-'phenylethylcimine (IV) and the corresponding ketone (V) have been obtained: •CH(OH)-CH2-NH2 (IV.) •CO-CH./NH, (V.) The physiological action of these substances has been investigated by Dr. H. H. Dale, Director of the Wellcome Physiological Research Laboratories, to whom we now express our thanks. It has thus been ascertained that both the bases (IV and V), when injected intravenously, have a pronounced influence on the blood-pressure. The intensity of the action of the keto-base is of the same order as that of the ketone corresponding with epinephrine, and it causes about one-tenth of the rise in blood-pressure produced by an equal weight of /3-p-hydroxyphenylethylamine, HO-Cr)H4*CH2*CHo*NH2 (Barger, this vol., p. 1123). The reduction of the ketonic group in Die monohydroxy-base (V) is, however, not attended with that ■enormous increase in activity which is observed when the ketone •corresponding with epinephrine is reduced, as /3-p-dihydroxy-