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

  • George Barger
Date:
1909
Catalogue details

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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    homologues by loss of carbon dioxide. That p-hydroxyphenylethyl- amine is indeed one of the products of the action of bacteria on tyrosine was shown by Barger and Walpole (Inc. cit.), and their recognition of its physiological action enabled Rosenheim (,/. Physiol. 1909, 38, 337) to trace the substance in placental extracts, the action of which on blood pressure and uterus was first observed by Dixon and Taylor (Bril. Med. Jonrn., 1907, ii, 1150). Rosen- heim also showed that such extracts are only active if the placenta has undergone a certain amount of putrefaction. Similarly, Van Slyke and Hart (Amer. Chan. ./., 1903, 30, 8) found y-hydroxy- phenylethylamine in Cheddar cheese, but not in cheese prepared under sterile conditions. Quite recently the base was also isolated from Emmenthaler cheese by Winterstein and Kiinz (Zeitsch. 'physiol. Chan., 1909, 59, 13S). In all the above investigations, ^-hydroxyphenylethylamine was only obtained in small quantities (generally as the dibenzoyl derivative). Even the method of preparation by the destructive distillation of tyrosine yields only small quantities. After the powerful and interesting physiological action of the substance became known, and after the substance had been recognised as the chief active principle of aqueous extracts of ergot, it became desirable to have a more convenient method of preparation, and this was found in the reduction of jJ-hydroxypheuylacetonitrile. The latter substance had already been prepared by Pscliorr, Wolfes, and Buckow (Ber., 1900, 33, 171), and readily yielded the desired amine on reduction with sodium and alcohol. It thus became possible to study the properties of the substance a little more closely, and particularly to investigate its behaviour towards methylating agents. Since the alkaloid hordenine, obtained by Leger (Compt. rend., 1906, 142, 108) from malt germs, is regarded as having the structure HO<^^>CH2-OH2*N(CH3)2, its synthesis, by methylation of p-hydroxyplienylethylamine, was attempted. By the action of methyl iodide on this base, a quaternary iodide is readily obtainable, which proved to be identical with hordenine methiodide. It is hoped that an account of these experiments, which are as yet incomplete, may be given later. Attention may also be drawn to the somewhat close chemical and physiological relationship between the active principle of ergot under discussion and the active principle of the adrenal gland, H°_ Iio/ \cH(OH)-CH2-NH-CH:t.
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