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Molecular Pharmacology, Vol 8, 269-277, Copyright © 1972 by the American Society for Pharmacology and Experimental Therapeutics

The Conformation of Acetylcholine and Related Compounds in Aqueous Solution as Studied by Nuclear Magnetic Resonance Spectroscopy

P. PARTINGTON 1, J. FEENEY 1, and A. S. V. BURGEN 1

1 Medical Research Council Molecular Pharmacology Unit, Medical School, Hills Road, Cambridge, England

The conformations of acetylcholine and 22 related compounds in aqueous solution have been determined by analysis of their NMR spectra. Gauche conformations depend on the presence of the onium group and the partial negative charge on the beta-oxygen. Good agreement is obtained with crystal structures, except for carbachol, which in solution has a gauche O/N+ conformation and in the crystal structure has a trans conformation.

There is no simple correlation between the predominant conformations and the potency of action of the drugs at either the nicotinic or muscarinic receptor.

Submitted on October 13, 1971




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