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Certain carbamate compounds, such as the insecticide carbaryl or the Edgewood carbamates such as EA-3990, can inhibit the enzyme acetylcholinesterase. Unlike organophosphorus compounds, however, they do so reversibly and are bound to the enzyme for minutes, as opposed to permanently. The carbamyl functional group differs from an acetyl group in that, instead of a methyl group being bonded to a carboxyl, a carbamate has amino group bonded to a carboxyl. Why exactly does this difference allow carbamates to inhibit AChE for minutes at a time, and why is cholinesterase that has been inhibited by a carbamate not susceptible to reactivation by oximes such as 2-PAM?

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