Acetylene compounds of potential pharmacological value. XXV. N- (4-pyrrolidino-2-butynyl) -N-alkylcarboxamides
Svensson, U.; Hacksell, U.; Dahlbom, R.
Acta Pharmaceutica Suecica 15(1): 67-70
1978
ISSN/ISBN: 0001-6675 PMID: 645369 Document Number: 138422
A large number of compounds related to the potent muscarinic agent oxotremorine, 1-(2-oxopyrrolidino)-4-pyrrolidino-2-butyne, were prepared, but very few showed tremorogenic activity in mice. Only 2 compounds seem to have activity of the same order of magnitude as oxotremorine, i.e., the dimethylamino analog of oxotremorine and N-(4-pyrrolidino-2-butynyl)-N-methylacetamide (I) whose tremorogenic activity is about 0.06 and 0.4 that of oxotremorine, respectively. Compound I may be regarded as an oxotremorine analog in which a lactam ring was opened between 2 methylene carbons. A compound of this type, N-(4-pyrrolidino-2-butynyl)butyramide, was reported to have properties similar to oxotremorine, though much weaker. It is a secondary amide whereas compound I is a tertiary amide.