The Nucleophilic Destruction of Some Model Riot Control Agents in Biologic Media

摘要

The nucleophilic destruction of the model riot control agents o-chlorobenzylidine-malononitrile (CS), phenacyl bromide, and N-benzylidineaniline was studied in biologic media. Upon contacting blood, these agents immediately bind to macromolecules and react under the influence of the microenvironment within the complex. As a result, their rates of destruction are either accela As a result, their rates of destruction are either accelerated or inhibited, depending on the mechanism of destruction and the biologic macromolecule. Upon entering the blood stream, CS apparently binds to plasma albumin, thus decreasing the rate at which it enters the tissues. In addition, albumin catalyzes the destruction of CS. Both mechanisms operate to protect the body from the toxic effects of CS. CS does not alkylate the catalyst. Phenacyl bromide apparently binds readily to serum albumin and alkylates its binding site. In the presence of hemoglobin, phenacyl bromide is destroyed so rapidly that the velocity constants could not be determined accurately. N-benzylidineaniline binds to several blood proteins. Its rate of decomposition is increased by fibrinogen and decreased by albumin. In human blood plasma the net rate of destruction of N-benzylidineaniline, however, is slowed only twofold. (Author)