2,5-Dimethoxy-4-substituted importance

DMA. None of the three possible tetramethoxy analogs has been investigated, and the pentamethoxy analog does not produce DOM-like stimulus effects. From these studies, it is apparent that the 2,4- and 2,5-dimethoxy substitution pattern plays an important role certain 2.6-dimethoxy derivatives are also active, depending upon what substituents are present at the 4-position. 

Analogous reactions with perfluoro(isopropyl-l,3,5-triazine) and per-fluoro(diisopropyI-l,3,5-triazine) with CsF yielded adducts 116 and 117, respectively, which were detected by 19F-NMR. Use of potassium fluoride, either alone or associated with 18-crown-6, did not lead to the formation of the adducts. In contrast, from tris(perfluoroisopropyl)-l,3,5-triazine no adduct was detected. This is quite interesting because it would indicate the importance of the gem-difluoro substitution to stabilize the adduct,160 in analogy with the effect of gem-dimethoxy substitution.76... 

Aza-annulation of a number of dimethoxy-substituted P-tetralone derivatives, such as those represented by 136, with acrylamide was used to produce 137. In turn, 137 was an important intermediate in the synthesis of conformationally restricted congeners of dopamine (eq. 30).53... 

The data in Table 2 agree well with results from an experiment by Clothier er al. (1981), who showed that bovine red blood cell AChE inhibited with dimethoxy-substituted compounds spontaneously reactivated and aged more rapidly than AChE inhibited by the dicthoxy-sub.stituted compounds. Importantly, however, the rate of spontaneous reactivation of the dimethoxy-substituted compounds was approximately an order of magnitude more rapid than the rate of aging. 

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