a-p-Hydroxy-m-methoxyphenylethylamine and the resolution of a-p-Hydroxyphenylethylamine / by Charles W. Moore.

  • Moore, Charles W.
Date:
[1911?]
Catalogue details

Licence: In copyright

Credit: a-p-Hydroxy-m-methoxyphenylethylamine and the resolution of a-p-Hydroxyphenylethylamine / by Charles W. Moore. Source: Wellcome Collection.

    4/10 page 417
    blood pressure somewhat similar to that of epinephrine, although in a less degree, and, since the former base contains an asymmetric carbon atom, it was considered of interest to ascertain whether the optically active bases, obtained by its resolution, would differ in physiological activity. a-p-Hydroxyphenylethyl amine d-camphor- sulphonate was therefore prepared and submitted to fractional crystallisation, when the salt of the lsevorotatory base was easily obtained in a pure condition. /-a-p-Hydroxyphenylethylamine <Acamphorsulphonate melts at 203—205°, and the specific rotation of the base contained in it, calculated from that of the salt, is [a]D — 7'9°. The salt of the d-base could not be obtained in a pure condition, the specific rotation of the base contained in it being [a]D + 6*9°. Optically pure benzoyl derivatives were, however, obtained from both of the stereoisomeric bases. The effect on the blood pressure of the l- and e^-bases was determined by Dr. IT. H. Dale, of the Wellcome Physiological Research Laboratories, to whom the author now expresses his thanks. No difference in physiological activity between the two bases was observed, and it is therefore evident that in this case the enantiomorphous forms possess an equal degree of physiological activity. A quantity of acetovanillone (4-hydroxy-3-methoxyacetophenone) being available, it was considered of interest to prepare the corre¬ sponding a-^-Jiydroxy-m-methoxy'phenylethylarrtme from it. This compound was obtained by the reduction of acetovanilloneoxime, and its hydrochloride and benzoyl derivatives have also been characterised. It has been found by Dr. H. H. Dale, as was anticipated, that the hydroxymetlioxy-base is slightly less active physiologically than the above-mentioned a-p-hydroxyphenylethyl- amine. Experimental. a-^-Hydroxy-m-methoxy'phenylethylamine. Acetovanillone (4-hydroxy-3-inethoxyacetophenone), as obtained from the rhizome of Ayocynum androsatmifolium, Linne (Moore, Trans., 1909, 95, 734), was converted into its oxime in the'usual manner. Eighteen grams of acetovanilloneoxime were dissolved in 250 c.c. of aqueous methyl alcohol, and twice the theoretical amount of 3 per cent, sodium amalgam gradually introduced, the mixture being kept acid by the frequent addition of acetic acid. When all reaction had ceased, water was added, the alcohol distilled off, and the aqueous liquid extracted with ether to remove unchanged oxime, after which it was rendered alkaline by means of sodium carbonate, and thoroughly extracted with amyl alcohol. The amyl-
    digitised image 1
    digitised image 2
    digitised image 3