40 



R. F. EUTTAN ON THE 



similar fluids without the alkaloid became foul withiu a few days. A fuller discussion 

 of the antiseptic as well as the therapeutic action of the base must be reserved for a 

 future paper. 



Although the experiments given above are quite insufficient to establish any thera- 

 peutic value for the alkaloid, yet the absence of all toxic effects, its regular action in the 

 three cases that were carefully observed, and its almost unique action on normal body 

 temperatures are both suggestive and interesting, especially so in view of the close rela- 

 tion that exists between its chemical constitution and that of some other alkaloids of 

 known value as antipyritics. 



Chemical Constitution. 



A molecular formula, or rather a systematic plan of the relative atomic groupings of 

 this compound, may be deduced from its general relations, chemical reactions, and espe- 

 cially from its mode of preparation. 



The question of the constitution of ortho-tolidin, from which this base is directly 

 derived, cannot be fully treated here — the large number of necessary references to sepa- 

 rate-compounds and reactions would take up too much space. The orientation of ortho- 

 tolidin, so far as its formula could influence that of a quinolin derived from it, has been 

 established by G-ustav Schultz.' In this formula C^ H,,, N^ he has shown the relative 

 position of atomic groups to be (C^ H^ : C H3 : N H. = 1 : 3 : 4). In the form of a diagram 

 this relation can be represented as follows : 



NH, 



NH, 



CH3 CH., 



In no case has it been established that in Skraup's reaction there is any alteration 

 in the relative position of the side chains in the benzol nucleus when the primary amine 

 is converted into its corresponding quinolin. In all cases it has been found that a side 

 chain in the benzol nucleus occupies a position towards the pyridin group formed by the 

 reaction similar to that which it had toward the amidogen grovip in the original aromatic 

 amine. 



The preparation of methyl quinolin from ortho-toluidin has been shown by Skraup's 

 reaction to be as follows : — 



CH3 CH3 CH3 



C 







H— C 



\ 



C— N H„ H— C : 



H— Cv /C— H 



C 

 Tî 



Ortho-toluidin. 



H— On 



C— N=CH— CH— OH, 



C-H 



C N 



H-C^ \/ ^C-H 



H-C 



C— H 







I 

 H 



Acrolein Ortho-toluidin. 



c c 



I I 



H H 



Methyl Quinolin. 



i"Beiichte,"xvii, 467. 



