%0 Journal Article %A REID HUNT %A R. R. RENSHAW %T FURTHER STUDIES OF THE METHYL CHOLINES AND ANALOGOUS COMPOUNDS %D 1934 %J Journal of Pharmacology and Experimental Therapeutics %P 237-262 %V 51 %N 2 %X 1. (a) The results of the early work of Hunt and Taveau (1911) on the pharmacological action of the acetyl ester of trimethyl-β-oxypropylammonium chloride ("acetyl-β-methy1 choline") are confirmed and extended. (b) This compound is very effective in lowering the blood pressure when injected subcutaneously. (c) Doses producing a marked fall of blood pressure cause few other effects. (d) It was the first very active choline compound made which does not, under some conditions, cause a rise of blood pressure, i.e., it has no "stimulating" nicotine-like action; it differs in this respect from choline, acetyl choline and many other derivatives of choline. (e) The "muscarine action" (the lowering of the blood pressure) of small doses was diminished or abolished by atropine but it was impossible to abolish the fall of pressure caused by lange doses by the injection of very lange doses of atropine. (f) It was very active in counteracting the hypertension caused by epinephrin, ephednine, posterior pituitary extract, methylguanidine, synephnin, barium chloride and the phenyl ether of choline. (g) The blood pressure lowering action was about 200 times as great as that of nitroglycerine. 2. (a) The pharmacology of trimethy1-β-oxypropyl-ammonium chloride ("β-methyl choline") is reviewed. (b) The early observations of Hunt and Taveau that this compound is less active both in causing a fall and a rise of blood pressure than is choline are confirmed. 3. (a) Propionyl-β-methyl choline is decidedly less active in lowering blood pressure than is acetyl-β-methyl choline. (b) It did not cause a rise of pressure after atropine. 4. (a) Propionyl choline is far more active in causing a fall of blood pressure than is choline; it is decidedly less active than acetyl choline. (b) It is almost as active as choline in causing a rise of blood pressure (after atropine). 5. (a) n-Butyril choline is about 200 times less active than acetyl choline in causing a fall of blood pressure. (b) n-Butyril choline was more active than propionyl choline in causing a rise of blood pressure; it was about five times as active in this respect as acetyl choline. (c) n-Butyril choline was more active than the iso-compound in causing a rise of blood pressure; the iso-compound was more active in causing a fall. (d) The iso-butyl ether of choline was quite active in causing a fall of blood pressure; it caused a rise of blood pressure after atropine. 1. A modification of the procedure used by Menge for the preparation of his "acetyl alpha methyl choline" is described. The product obtained proved to be acetyl beta methyl choline. Since the modifications in procedure were all in the direction of preventing or lessening rearrangement it is safe to state that Menge's "alpha" product, with which some of Hunt's early work was done, was pure acetyl beta methyl choline. From these results and from those of Major and Cline and of Karrer, it is clear that Hunt deserves the credit for having been the first to call attention to the physiological action of acetyl beta methyl choline as he had also done for acetyl choline, the two compounds of this class which have proved to be of most interest in pharmacology and medicine. 2. A simplified method for the preparation of acetyl beta methyl choline is described. %U https://jpet.aspetjournals.org/content/jpet/51/2/237.full.pdf