76 MEDULLA 



that methylamine could be split off from the compound sug- 

 gested the presence of a methylamino group in the side chain. 

 Friedmann 207 oxidized the tribenzenesulphonyl derivative of 

 epinephrine to a ketone, thereby demonstrating the existence 

 of a secondary alcoholic grouping in the side chain. It thus 

 became probable that epinephrine was represented by the 

 structural formula 



OH 

 lOH 



CH(OH).CH 2 NHCH 3 



which conforms to the requirements of the reactions cited 

 above. The existence of an asymetric carbon atom in this 

 formula accounts for the optical activity manifested by epi- 

 nephrine solutions, as first observed by Pauly. 487 



The systematic name for epinephrine as represented by the 

 above formula is dioxyphenylethanolmethylamine, a-methyl- 

 amino-j3-hydroxy-j3-(3 , 4-dihydroxyphenyl) ethane, or methyl- 

 aminoethyl-(3 , 4-dioxyphenyl)-carbinol. 



The ultimate proof of the correctness of the above described 

 formula was furnished by Dakin 146 and Stolz 599 who synthesized 

 epinephrine. This synthesis, which has received commericial 

 application for the preparation of the compound, consists of 

 the following steps: 



OH OH 



iOH AOH 



+ CH 2 C1C0C1 ► + HC1 



COCH 2 Cl 



(Catechol) (Chloracetylchloride) (Chloracetocatechol) 



OH OH 



0H +CH3NH, > Q 0H 



COCH 2 Cl COCH 2 NHCH 3 



(Methylamino-ketone of 

 paracatechuic acid) 



The last compound on reduction yields epinephrine. 



