Synthesis of hordenine, the alkaloid from barley / by George Barger.

  • Barger, George, 1878-1939.
Date:
1909
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Synthesis of hordenine, the alkaloid from barley / 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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    CCXXXV.—Synthesis of HorcLenine, the Alkaloid from Barley. By George Barger. A few years ago Leger (Gompt. rend., 1906, 142, 108) isolated from barley germs a crystalline alkaloid, which he named hordenine, and subsequently {Gompt. rend., 1906, 143, 234, 916) gave the following constitution: OH<^ \CH2-CH2-N(CH3)2. This constitutional formula was confirmed by/ Gaebel (Arch. Pharm., 1906, 244, 435), and the physiological action of hordenine was studied by Camus (Arch. int. de Pharmacodijn. et de Ther., 1906, 16, 43). It is evident that hordenine (p-hydroxyphenylethyldimethyl- amine: a-dimethylamino-j8-p-hydroxyphenylethane) is closely related to p-hydroxyphenylethvlamine, a physiologically active base of somewhat wide distribution, and the author’s recent synthesis of the latter base (this vol., p. 1123) suggested an attempt to prepare hordenine from it by methylation. This attempt was not wholly successful, for although the methiodide of hordenine was readily obtained by treating 2?-hydroxy- phenylethylamine with methyl iodide, it was found impossible to isolate the alkaloid itself; the reaction did not stop at the tertiary base, but resulted in the formation of the quaternary iodide, no