Isolation and synthesis of p-hydroxyphenylethylamine : an active principle of ergot soluble in water / by George Barger.

  • George Barger
Date:
1909
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Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Isolation and synthesis of p-hydroxyphenylethylamine : an active principle of ergot soluble in water / by George Barger. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    CXXVII.—Isolation and SynA In a paper on the alkaloids of ergot, F. H. Carr and the author (Trans., 1907, 91, 337) described the amorphous alkaloid ergotoxine, to which many of the characteristic physiological effects of ergot are due. This alkaloid is, however, only present in small quantities in most specimens of the pharmacopoeial preparations of ergot, and, in discussing the latter, H. H. Dale and the author (Biochem. J., 1907, 2, 286) postulated the presence of a second active principle soluble in water. Attempts to isolate this hypothetical principle were for a long time unsuccessful. Vahlen (Arch, exper. Path. Phann., 1906, 55, 131) seems also to have been aware of the existence of such a principle, but his so-called “ clavin ” has been shown to be an inert mixture of amino-acids, in which leucine predominates (Barger and Dale, Biochem. J., 1907, 2, 288). The physiological properties of jj-hydroxyphenylethylamine, recently isolated from putrid meat by Barger and Walpole (.7. Physiol., 1909, 38, 343), suggested that this base might be the above-mentioned active principle of aqueous ergot-extracts. It has indeed been possible to prove that yhydroxyphenylethylamine occurs in such extracts, and that the presence of this base accounts in a satisfactory manner for such of the activity as is not due to small quantities of ergotoxine (see Barger and Dale, Proc. physiol. Soc., May 15th, 1909; the physiological experiments have been performed by Dr. H. H. Dale). The method of isolation, described below, was based on the process employed in tl^e case of putrid meat, but required further elaboration on account of the large amount of resinous constituents of ergot which are soluble in water. p-Hydroxyphenylethylamine has figured several times in chemical literature. It was first prepared in small quantities by Schmitt and Nasse (Annalen, 1865, 133, 214), who obtained it by heating tyrosine. Subsequently it was isolated by Emerson (Beitr. chem. Physiol. Path., 1902, 1, 501) from autolysed pancreas, and by Langstein (ibid., 1902, 1, 507) in prolonged peptic digestion of egg-albumin. Gautier (Bull. Soc. chim., 1906, [iii], 35, 1195) isolated the base, together with a lower and a higher homologue, from the mother liquors obtained in the putrefaction of cod-livers. He suggested for these bases the general name “ tyrosamine,” since they may be considered as being derived from tyrosine and its ethylamine, an Active in Water. By George Barger. too,