Some new physiologically active derivatives of choline / by A.J. Ewins.

  • Ewins, Arthur James.
Date:
[1914?]
Catalogue details

Licence: In copyright

Credit: Some new physiologically active derivatives of choline / by A.J. Ewins. Source: Wellcome Collection.

    4/10 (page 367)
    I prepared a number of the simpler choline derivatives which might possibly give a clue to the constitution of the natural base. So far the investigation has not led to the identification of muscarine itself, but certain of the deriva tives prepared were of some considerable interest, the ethyl ether of choline OH . N(CH3)3 . CH2 . CH2.0 . C2H5 in particular being very closely related indeed in its actjjptwto that of the natural muscarine. The bases were in all cases physiologically examined by Dr H. H. Dale, whose results will be published shortly. The following is a table of the substances examined : (1) (2) (3) (4) (5) (6) (V) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) Acetyl-choline Formyl-choline Lactyl-choline Choline nitrous acid ester Choline nitric acid ester Choline methyl ether Choline ethyl ether Choline propyl ether Choline ether OH. OH , OH OH OH OH OH OH OH N(CH3)3CH2CH20 . OCCH3. , N(CH3)3CH2CH20 . OCH. . N(CH3)3CH2CH20 . chch3. N(CH3)3CH2CH20 N(CH3)3CH2CH20 N(CH3)3CH2CH20 N(CH3)3CH2CH20 N(CH3)3CH2CH20.C2H5, CO. NO. NOo CH,. N(CH3)3CH2CH20 . c3h7. OH . N(CH3)3CH2CH20 . CH2CH2N(CH3)3OH. Trimethyl-^-bromo-ethyl-ammonium bromide BrN(CH3)3CH2CH2Br. Trimethyl-/3-chloro-ethyl-ammonium chloride C1N(CH3)3CH2CH2C1. Trimethyl-[3-cyano-ethyl-ammonium hydroxide OH . N(CH3)3CH2CH2CN. Trimethyl-(3-amino-ethyl-ammonium hydroxide OH . N(CH3)3CH2CH2NH2, Dr’■methyl-oxazolium hydroxide Formocholine methyl ether Formocholine ethyl ether Formocholine propyl ether Formocholine butyl ether (OH) N(CH3)2—CH2 ch2 OH . OH , OH . OH ,CH2.0 N(CH3)3CH2OCH3. N(CH3)3CH2OC2H5. N(CHo)3CH2OC3H7. , N(CH3)3CH2OC4H9. All of these bases showed considerable physiological activity, those ap¬ proaching most nearly to muscarine being choline ethyl ether, choline nitric acid ester, and trimethyl-/3-amino-ethyl ammonium hydroxide. The curare¬ like action of all of these is, however, more pronounced than in the case of natural muscarine. The ethers of formocholine were found to possess an action closely resem¬ bling that of the corresponding choline ethers, but were quantitatively much less powerful. Formocholine propyl ether was found to be the most active of the series whereas the isomeric choline ethyl ether was the most active of the choline ethers. The compounds printed in italics in the above table are new substances. Their preparation and properties are described below. The remaining bases were obtained by the methods previously employed by other workers, notably Schmidt and Wagner [1904] and Nothnagel [1894].