AMINES DERIVED FROM AMINO-ACIDS 



185 



The greatest importance of this process from a biochemical point of 

 view arises out of the intense physiological activity of many of the 

 products which originate in this manner, the resemblance of some of 

 these products to the active principles of certain of the glands of 

 internal secretion, and from the probability that some of them may 

 reach the circulation, occasionally in injurious quantities, by absorp- 

 tion from the large intestine wherein they are produced by bacterial 

 activity. 



The following amines have been produced from the corresponding 

 amino-acids by the action of putrefactive bacteria. It is possible, 

 however, that the true source of methylamine in the putrefaction 

 of fishes is not glycocoll, but choline (trimethyl oxyethyl ammonium 

 hydroxide) which is the basic constituent of Lecithin. 



Amino-acid. Amine. 



Glycocoll, CH 2 .NH 2 .COOH Methylamine, CH 3 NH 2 



Alanine, CH 3 .CH.NH 2 .COOH Ethylamine, CH 3 CH 2 NH 2 



Valine, 



cH.CH(NH 2 ).COOH 



Isobutylamine, 



CH.CH 2 NH 2 



CH; 



\ 



Leucine, 



\ 



CH.CH 2 .CH(NH 2 ).COOH Isoamylamine, ^>CH.CH 2 CH 2 .NH 2 



CH/ 



CH 



3 \ 



CH 3 v 



Isoleucine, NcH.CH(NH 2 ).COOH Ethylmethyl ethylamine \CH.CH 2 NH 2 



c 2 H 6 / C Z H/ 



Phenylalanine, C6H 5 CH 2 .CH(NH 2 ).COOH Phenylethylamine, C 6 H 5 .CH 2 .CH 2 .NH 2 

 Tyrosine, HO.C 6 H 4 .CH 2 .CH(NH 2 ).COOH p-Hydroxyphenylethylamine (tyramine), 



HO.C 6 H 4 .CH 2 CH 2 NH 2 

 ,NH 2 



Guanido-butylamine (agmatine) , 



/NH 2 

 NH.CH 2 .CH 2 .CH 2 .- 



CH(NH 2 ).COOH HN = 



Arginine, HN 



^NH.CH 2 .CH 2 CH 2 CH 2 NH 2 



Lysine, H 2 N.CH 2 .CH 2 CH 2 .CH 2 .CH(NH 2 ).- Pentamethylene-diamine (cadaverine), 



COOH H 2 N.CH 2 CH 2 .CH 2 CH 2 .CH 2 NH 2 



Ornithine, H 2 N.CH 2 CH 2 .CH 2 .CH(NH 2 ).- Tetramethylene-diamine (putrescine), 



COOH 



Histidine, 



CH 



/ \ 



N 



H 2 N.CH 2 .CH 2 .CH 2 .CH 2 NH 2 



Iminazoylyl ethylamine (histamine, erga- 

 mine), 

 CH 



NH 



CH = C.CH 2 .CH(NH 2 ).COOH 

 Tryptophane, C.CH 2 .CH(NH 2 ).COOH 



/\ 



C 6 H 4 CH 



\/ 



NH 



N 



CH 



NH 



C.CH 2 .CH 2 .NH 2 

 Indolethylamine, C.CH 2 CH 2 NH 2 



/\ 



/ \ 



C 6 H 4 CH 



\/ 



NH 



