134 REPORTS ON INVESTIGATIONS AND PROJECTS. 



other, and that it has the chemical structure of an open chain or cyclic 

 hydrazide. Such experiments as have been made by the writers 

 induce them to believe that the base is a new and highly unstable 

 cyclic hydrazide. The search for hydrazine or methylhydrazine 

 among the decomposition products of epinephrin hydrate itself has 

 not been rewarded thus far with success ; but by means of appropriate 

 methods skatol, protocatechuic aldehyde, and vanillin were obtained 

 as decomposition products. 



In consequence of the results obtained the writers are led to believe 

 that epinephrin hydrate, 2 (C 10 H 13 NO 3 ^H 2 O), contains not only the 

 protocatechuic complex, C 6 H 3 .(OH) 2 C, but also the vanillic residue 

 C 6 H 3 .OH.(O.CH 3 ).C. These aromatic residues are combined with 

 a side chain containing two nitrogen atoms, one of which is present 

 as a part of the group .NH(CH 3 ), the other as a part of the group 

 :NH. A further analysis of atomic groupings has not been attempted, 

 especially in respect to the disposition of the hydroxyl groups which 

 must be assumed to be present in the side chain of the molecule. 

 The above arguments, together with others, have been duly set 

 forth as objections against the validity of the constitutional formula 

 C 6 H 3 (OH) 2 .CH.OH.CH 2 .NH.CH,, now generally accepted as cor- 

 rectly representing the structure of the substance under discussion. 



Some experiments were undertaken with the purpose of forming 

 synthetically a number of physiologically active compounds which 

 should contain one or more hydroxylated benzene residues associated 

 with a nitrogenous complex containing two atoms of nitrogen. 



Acree, Solomon F., Johns Hopkins University, Baltimore, Maryland. 

 Grant No. 204. Study of pinacoyie-pinacolin rearrangem.C7it a?id 

 of urazoles. $1,000. 



Report.— -In an article entitled " On the pinacone-pinacolin rear- 

 rangement (I)," which appeared in the American Chemical Journal, 

 February, 1905, were described some new classes of pinacones and 

 pinacolins and the rearrangements which these compounds undergo 

 under certain conditions. In connection with this a new series of 

 trialkyl glycolls, prepared by a method originated by the writer, 

 was studied. 



In an article now in course of preparation, "On the pinacone-pin- 

 acolin rearrangement (II) : Reaction of sodium pinaconates," will 

 be published the results of investigations on sodium pinaconates. 

 These interesting compounds, in contrast to the corresponding pina- 

 cones or the bromagnesium salts, are very reactive toward air, water, 

 acids, acid chlorides, carbon dioxide, aldehydes, ketones, esters, and 



