AMINES DERIVED FROM PROTEIN 21 



The constitution of hordenine was deduced by Leger from the oxi- 

 dation of acetyl-hordenine to acetyl-p-hydroxy-benzoic acid and the 

 distillation of the ammonium base from hordenine methiodide 

 methyl-ether, which yielded trimethylamine and p-vinylanisole, 



CH 3 O.C 6 H 4 .CH:CH 2 . 



Gaebel, on methylating and oxidising, obtained anisic acid from 

 hordenine. 



The synthesis of hordenine was first carried out by Barger [ 1 909, 2] 



from phenyl-ethyl -alcohol, a commercial product, as follows : 



C 6 H 5 . CH 2 . CH 2 . OH-C 6 H 5 . CH 2 . CH 2 . C1-C 6 H 6 . CH 2 . CH 3 . N(CH 3 ) 2 



I 

 HO.C 6 H 4 .CH 2 .CH 3 .N(CH 3 ) 2 <-NH 2 .C 6 H 4 .CH 3 .CH 2 .N(CH 3 ) 2 -N0 2 .C 6 H 4 .CH 3 .CH 3 .N(CH 3 ) 2 



Closely related to this is the synthesis from tyrosol, by Ehrlich 

 [1912]:- 



OH . C 6 H 4 . CH 3 . CH 2 OH->OH . C 6 H 4 . CH 2 . CH 2 C1->OH . C 6 H 4 . CH 2 . CH 2 . N(CH 3 ) 2 

 The attempted conversion of p-hydroxy-phenyl-ethylamine into horde- 

 nine by methyl-iodide resulted only in the formation of the quaternary 

 iodide, but Rosenmund [1910] has succeeded in methylating p-methoxy- 

 phenyl-ethylamine to the tertiary base, hordenine methyl-ether, from 

 which hordenine was obtained by boiling with hydriodic acid. Other 

 syntheses are by reduction of p-hydroxy-phenyl-dimethyl-amino-methyl- 



ketone 



HO . C 6 H 4 . CO . CH 2 . N(CH 3 ), 



(Voswinckel [1912]) and by distillation in a vacuum of the quaternary 

 hordenine methiodide (prepared from p-hydroxy-phenyl-ethylamine) 

 according to D.R.P. 233069 of Farbenfabriken vorm. F. Bayer & 

 Co.: 



OH . C 6 H 4 . CR, . CH 2 . N(CH 3 ) 3 I = OH . C 6 H 4 . CH a . CH a . N(CH 3 ) 2 + CH 3 I . 



Hordenine has only a transitory existence during the germination of 

 barley. According to Torquato Torquati [1910] it is not present in the 

 ungerminated seed and is most abundant after four days, when the 

 rootlets contain 0-4 - 0*45 per cent. It then gradually diminishes 

 and has disappeared after twenty-five days. It is absent in germinating 

 wheat, peas and lupins. 



Indolethylamine (3-/3-Amino-ethylindole), C 10 H 12 N 2 . 



3-/3-Amino-ethylindole is the amine derived from tryptophane by 

 decarboxylation. It was obtained by Ewins and Laidlaw [1910, 2] 

 both synthetically and by the action of putrefactive bacteria on the 

 amino-acid. 



The synthesis, subsequently described by Ewins [1911], is the 



