4-[beta]-aminoethylglyoxaline ([beta]-iminazolylethylamine) and the other active principles of ergot / by G. Barger and H.H. Dale.

  • Barger, George, 1878-1939.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: 4-[beta]-aminoethylglyoxaline ([beta]-iminazolylethylamine) and the other active principles of ergot / by G. Barger and H.H. Dale. 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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    amylamine (from leucine) is probably present in ergot, but in such proportion that it makes no significant contribution to the physiological action. After the isolation of p-hydroxyphenylethylamine, there still remained unaccounted for the powerful .action of certain aqueous ergot extracts in producing contraction of the isolated uterus, even of the non-pregnant cat, as observed by Kehrer. Since it was found quite impossible to remove the active substance from aqueous solution by means of organic solvents, a precipitation method had to be employed, and the ergot extract was subjected to the process worked out by Kutscher for the isolation of bases from meat extract. In this way we obtained a minute quantity of a crystalline picrate which gave Pauly’s reaction with p-diazobenzenesulphonic acid, and exhibited in an intense degree the physiological action in question. It was not histidine picrate, for histidine was found to be inert j we therefore supposed it to be the picrate of 4-)8-amino- ethylglyoxaline (3-iminazolylethylamine), the base which would result from histidine by the loss of carbon dioxide; H,)-CO,H = 9 + CO, and we confirmed this supposition by chemical and physiological comparison with a specimen of 4-j8-aminoethylglyoxaline, very kindly sent us at our request by Dr. D. Ackermann, who a short time before had obtained this base by the putrefaction of histidine {Zeitsch. physiol. Chem., 1910, 65, 504). Simultaneously with our- selves, Kutscher {Ztntr. Physiol., 1910, 24, 163) obtained a very active base from ergot, which he considered to be closely related to 4-)3-aminoethylglyoxaline, although not identical with it, on account of a supposed difference in the physiological action of the two bases. It has, however, recently been shown that the differences in physiological action observed by Kutscher were presumably due to differences in the animals employed. One and the same base, whether from ergot or from histidine, can be made to produce the different effects described by Kutscher. On the other hand, the base from ergot and that from histidine, when tested successively on the same animal, gave identical effects. We have also analysed the picrate of the base from ergot, and have compared it and the picrolonate with the corresponding salts of 4-)3-aminoethylglyoxaline (from histidine). As a result, we maintain our original conclusion (Proc., 1910, 26, 128) that, contrary to Kutscher’s view, the base in question is identical with 4-)3-aminoethylglyoxaline. It is there- fore the second active principle of ergot belonging to the class of putrefaction bases derived from amino-acids. Its physiological activity is very great. A marked contraction of the isolated uterus