THE ALUMNI JOURNAL, 



39 



cetin contains likewise an oxy-methyl 

 group in the para position, these two 

 bodies, contrary to anticipations have 

 a weaker effect than acetanilid, which 

 is however accounted for by their com- 

 parative insolubility and difficulty in 

 splitting up in the organism. Exalgin, 

 a methylated acetanilid because of its in- 

 solubility suffers a loss in antipyretic 

 effect, acettoluid is likewise feebly anti- 

 pyretic. 



On the contrary, increased solubility 

 does not always indicate increased activ- 

 ity, for example, Schering in order to in- 

 crease the solubility of phenacetin, intro- 

 duced an amido-group NH^ in the side 

 chain which enabled it to readily form 

 salts, thus the hydrochloride of pheno- 

 coll is soluble i in 20 and yet it is given 

 in same doses as phenacetin. Neurodin* 

 an aceto-p-oxyphenylurethane, in doses 

 of I gramme is an active antineuralgic. 

 Through the introduction of an ethyl 

 group as in thermodin we find it to be 

 antipyretic in doses of 0.5 gm. 



Phenyl-hydrazin CeHsNH— NH„ you 

 will remember, may be considered a de- 

 rivative of anilin, in which a H is re- 

 placed b}' an amido group; on introduc- 

 ing an acetyl group (CH3CO) in this, 

 hydracetin 



/acetyl-phenyl -hydrazin \ 

 VCeHsNH— NH— CH3CO / 



was formed, this owing to its powerful 

 toxic properties (dose o 05) was not 

 favorably received, Knorr took up this 

 idea and by forming a condensation pro- 

 duct between phenyl-hydrazin and ethyl- 

 aceto-aceticester (CH3— CO,— CH,— CO- 

 OC2H3) and this on methylating yielded 

 phenyl-di-methyl -pyrazolon or antipyrin 



N— CeH, 



Since this discovery, numerous experi- 

 ments have been made to produce bodies 

 of equal therapeutic value, by introducing 

 certain groups into the phenyl radical, 

 thus Riedel prepared a methyl derivative 

 by introducing a methyl group in the 

 para position of the phenyl group, which 

 he named tolypyrin. 



N-CeH— CH3 



0=C 



Hg= 



|N- 

 =C- 



-CH3 

 -CH, 



p-tolyl-di-methyl- 

 pyrazolon. 



Comparative experiments have shown 

 that this new body is equal to antipyrin^ 

 not only in degree, but also in the art of 

 its therapeutic action. In most cases 

 four gms. of tolypyrin performed the 

 same work of 6 gms. antipyrin. 



As Thomsf has suggested, the intro- 

 duction of an alkyl or oxy-alkyl group 

 in the benzene nucleus reduced the ener- 

 getic action of acetanilid, with this view 

 he prepared a like derivative of antipyrin, 

 to note the effect produced by these 

 groups in the benzene nucleus to the 

 pyrazolon ring. N— CeH^ — OC0H5 



OC 



NCH, 



HC= 



=CCH, 



0==C 



HC= 



IN— CH3 



=C— CH, 



*Von Meriiig Therapeut Moiiatsh, '93-/-577. 

 fPhar. Ceuth. '93-145 



Para - antipyrin (p - ethoxy - phenyl - 

 dimethyl-pyrazolon) was prepared, and 

 from clinical experiments, it was found 

 that instead of diminishing the effect of 

 antipyrin, the ethoxy group increased it 

 to such an extent as to render it useless 

 in medicine. That the introduction of a 

 methyl group in antipyrin has given a 

 more powerful body tolypyrin, finds con- 

 firmation in the fact that cresol 



OFT 

 CeH^<C^pTT which differs from phenol 



CgHs OH only in a methyl group is char- 

 acterized by a stronger antiseptic action. 

 That we find the secondary effects of 

 antipyrin suppressed in tolypyrin may be 



