CHEMISTEY OF THE SUPBAKENAL GLANDS 87 



acts much like adrenalin although it is much less active (1-100). Dakii 

 found that hydroxyethylmethylamin, which is the side chain in adrenalin, 

 exerts slight, if any, pressor activity, while pyrocatechol is active to some 

 extent. 



A quinolin derivative (3-amino-a-hydroxy (quinolyl 4) ethan, is 

 claimed to exert an action on blood pressure like homorenon. 



Synthetic adrenalin differed slightly from the 1-adrenalin in that the 

 melting point was lower and it formed a well crystallizable oxalate. 

 Qualitative physiological tests showed it to exert all the physiological 

 actions of the natural base. Some of the clinical reports at first indicated 

 that synthetic adrenalin was even more active than the natural variety, 

 but this was probably due to the greater purity of the preparation used 

 and Biberfeld(a), who studied the action of synthetic adrenalin on rabbits, 

 claimed it was as active as 1-adrenalin, but Cushny (&) (c) repeated the ex- 

 periments on blood pressure, using dogs, and showed that the synthetic 

 variety was only one-half as active as the natural form and that rabbits 

 were not suited for repeated injections such as had been used for this 

 test, as they become tolerant to the action of adrenalin. 



Schultz tested commercial samples of synthetic (dl) suprarenin and 

 compared them with adrenalin, purified by Abel's method. He found their 

 pharmacological action was in relation of 2 to 3. There might be some 

 question whether the samples of synthetic suprarenin sent by the manu- 

 facturers to Cushny might not have been purer than those bought on the 

 market by Schultz and this might explain the slight differences between 

 the results of Cushny and of Schultz. 



By means of tartaric acid, Flacher separated synthetic suprarenin into 

 bitartrates of the d- and 1- forms. The separation may also be car- 

 ried out by means of Penicillium glaucum. The dextro-form can be race- 

 mized by treatment with acids and, by again separating, the yield of 

 the levo-rotatory form may be increased. 



Cushny tested d-adrenalin and found it 1-12 as active as the 1-form 

 both as to its action on blood pressure and in its toxicity. Under these 

 conditions the manufacturers decided to market only the 1-form under 

 the name "synthetic suprarenin." 



It might be of interest to see if the d-adrenalin has any of the proper- 

 ties which Abel ascribed to alkaloidal epinephrin. It gives the chemical 

 reactions of the levo-variety (Borberg). So far as we know d-adrenalin 

 has not been found in the suprarenal gland or its extracts. d-Adrenalin 

 is much less toxic than the levo-rotatory variety and, in mice, its injection 

 seems to render them more resistant than usual, to the latter. It was 

 claimed to lessen or annul the pressor action of the natural variety (Ab- 

 derhalden and Slavu; Abderhalden and Kautzsche; Abderhalden, Kautz- 

 sche and Mliller; Ogawa, Waterman (6), Frohlich(a-)). 



