Vinyl ethers of choline and congeners

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Abstract
The vinyl ethers of choline and of its .alpha.- and .beta.-methyl homologues were prepared to determine their cholinergic effects [in guinea pigs and dogs] and to determine whether a separation of the dual physiologic activity (nicotinic and muscarinic) reported for the vinyl ether of choline could be achieved by this modification. A literature method of vinyl transetherification of amino alcohols was studied and modified. The ethyl ethers of choline and of .alpha.- and .beta.-methylcholine were prepared for comparison with the vinyl ethers. Two independent, unequivocal syntheses of the ethyl ether of .beta.-methylcholine were accomplished. The 2 literature methods for synthesis of this compound were equivocal, and, hence, the biological data reported for this compound in the older literature may not be valid. Certain of the ethers showed marked nicotinic or muscarinic activities.

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