1, 2-Disubstituted cyclohexanes as substrates of acetylcholinesterase and muscarinic agents. A re-investigation

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Abstract
The previously reported high rates of acetylcholinesterase‐catalysed hydrolysis of (±)‐cis‐ and (±)‐trans‐2‐dimethylaminocyclohexyl acetate methiodide (Baldridge, McCarville & Friess, 1955) have been re‐investigated, the enantiomers of each geometrical isomer being used. The cis‐enantiomers were inactive as substrates and the trans‐enantiomers were hydrolysed at a very slow rate. These results are confirmed by studies on muscarinic tissue (guinea‐pig ileum) in which only a weak stimulatory response was given with the trans‐enantiomers (the cis‐enantiomers were inactive). With each of the test systems used, the acetylcholine receptor showed an inversion of the “normal” configurational specificity although the enantiomer potency ratio was small, a phenomenon which has been observed in previous reports of inversion of configurational specificity.