N,N-Diethyl-m-toluamide Pathway Map

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This pathway was contributed by Sarah Huebert, University of Minnesota, BioC/MicE 5309.

N,N-Diethyl-m-toluamide, commonly known as DEET, is broadly used as an active ingredient in insect repellents (Rivera-Cancel et al., 2007). In the United States, 30% of people use an insect repellent containing DEET at least once a year (McGready et al., 2001). Annual domestic use equals approximately 1,800 tons (Rivera-Cancel et al., 2007). DEET was originally patented by the United States Army for use in insect-infested areas and was later registered for use by the general public. DEET is not known to have carcinogenic effects on humans (EXTOXNET; Pesticide Information Profile: DEET). While not carcinogenic, exposure to N,N-diethyl-m-toluamide does have human health effects including skin reactions and in rare cases of high-level exposure, seizures, toxic encephalopathy, acute manic psychosis and death (TOXNET; Hazardous Substances Data Bank; DEET).

Hydrolysis of the amide bond in N,N-Diethyl-m-toluamide yields 3-methylbenzoate and diethylamine. This transformation is catalyzed by the enzyme DEET hydrolase under aerobic conditions by the bacterium P. putida DTB. The resulting 3-methylbenzoate is then converted to 3-methylcatechol which can be further metabolized through the meta cleavage pathway of Pseudomonas putida (Rivera-Cancel et al., 2007). Diethylamine and ethylamine are both hydrolyzed to acetaldehyde before entering central metabolism (Steenkamp et al., 1976). In laboratory batch experiments with activated sludge from a membrane bioreactor, the two main products observed were the product of enzymatic dealkylation and the product of enzymatic oxidation.

The following is a text-format N,N-diethyl-m-toluamide pathway map. An organism which can initiate the pathway is given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (4k) format. 

 
					N,N-Diethyl-m-toluamide    
         			        Pseudomonas putida DTB 
				     and aerobid mixed culture from 
				       activated sludge treatment
		 				  |
 	    	   +------------------------------+------------------------------+
 		   |		                  |			         |
 		   |deet                 	  |deet		                 |deet
  		   |monooxygenase 	          |hydrolase	   	         |dehydrogenase
 		   |                   	     	  |		  	         |
 		   v                  	  +-------+--------+		         v
  		N,N-diethyl-3-            |                |                m-Toluamide
 	   (hydroxymethyl)benzamide       |                |
 		   |                      |          	   |                
  		   |           	          v                v
  		   |		  m-Methylbenzoate   Diethylamine                                                       
		   |N,N-diethyl-3-        |                |
 		   |(hydroxymethyl)benzamide               |
  	  	   |dehydrogenase   	  |                |trimethylamine
        	   v		  	  |                |dehydrogenase  
	    N,N-diethyl-3-        	  |                |
       	    formylbenzamide	      	  v        +-------+--------+
 		   |                    to the     |                |          
  		   |                   m-Xylene    |                |  
  		   |                   Pathway     |                |
 		   |                               v                |     
 		   |N,N-diethyl-3- 	     Ethyl amine	    |      
 		   |formylbenzamide            	   |                |  
 		   |dehydrogenase		   |                |           
  		   v         		 	   |methylamine     |                 
          3-(diethylcarbamoyl)    		   |dehydrogenase   |
              benzoic acid            	   	   |                v
                                          	   +---------->Acetaldehyde                        
                                                       		    |
                                                      		    |
                                       			            |                                      				
								    |
                                       				    v                               
                                  			       Intermediary
                                   			  	 Metabolism 
                                     				  (KEGG)
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Page Author(s): Sarah Huebert

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