ANALOGUES 



The following compounds were found to have no appreciable 

 activity in rats : 



6 : 7-dimethyl-9-(D-i'-xyhtyl)-isoalloxazine3 

 -9-(L-i '-^hamnityl)- 

 -9-(D-I'-arabityl)- 

 7-methyl-9- (D- 1 '-dulcityl) - 

 -9-(L-i'-arabityl)- 

 -9-(D-i'-sorbityl)- 

 -9- (D- 1 '-mannityl) - 

 6 : 7-dimethyl-9-(L-i'-ribityl)- 

 „ -9-(D-iMyxityl)- 



-9- (D- 1 '-desoxyribityl) ■ 

 7-ethyl-9- (D- 1 '-ribityl) - 

 6-ethyl-7-methyl-9- (L- 1 '-arabityl)- 

 5 : 6-benzo-9- (D- 1 '-ribityl) - 

 -9-(L-i '-arabityl)- 

 6 : 7-dimethyl-9-(D-ribosido)- 



-9- (L-arabin osido) - 

 6 : 8-dimethyl-9- (D- 1 '-ribityl) - 



-9- (L- 1 - 'arabity 1) - 

 5 : 7-dimethyl-9-(D- 1 '-ribityl) - 

 „ -9-(L-i'-arabityl)- 



Several of these compounds were also tested on S. casei and L. 

 lactis acidi, and were likewise found to be inactive.'' 



6 : 7-Dimethyl-9-(D-i'-lyxityl)-isoalIoxazine (lyxofiavine) has been 

 isolated from the human myocardium, 5 mg. being obtained from 

 10 kg.i2« 



The preparation of compounds related to lumiflavine was described 

 by H. Lettre and M. E. Fernholz.12 These were a series of 9-alkyl- 

 5 : 6-benzofia vines, made by condensing alloxan with 9-substituted 

 naphthalene-o-diamines . The substituents ranged from the methyl to 

 the cetyl group, and all the compounds were sparingly soluble in water. 

 When injected subcutaneously, a water-soluble flavine of unknown 

 constitution appeared in the urine within one hour of the injection. 

 None of the compounds was active. 



Isoribofiavine (5 : 6-dimethyl-9-D-i'-ribityl-isoalloxazine) (I) and 

 2-amino-4 : 5-dimethyl-i-ribitylamino-benzene (II) : 



CH2 — (CHOH), • CH.OH 



CH, 



CH3 



N. 



/NH 



CO 



CH3 



CHj^ 



NH • CH2 • (CHOH) 3 • CH2OH 



\ 



NH, 



II. 



had little growth-stimulating effect on Lactobacillus helveticus, but 

 were able to enhance the effect of traces of riboflavine or flavine 



207 



