DIAMINE OXIDASE (hISTAMINASE) 



361 



H3N— (CH2)— NHa"" 

 Cadaverine 



Putrescine 



H3N— (CH2 )3— ^fH— (C H2 )4— NH — (CH2 )3— NH^ 



*2M 



Spermine 



CH3— (CH3)^C^ + 

 Monoamidines 



HjN^ , , /NH2 



HzN'^ NH2 



Diamidines 





/=\ /NH3 



Dibenzamidines 



H,N— C 



^NH— CH3 



Methylguanidine 



H,N-C 



'NH^ 



-NH— NH2 

 Aminoguanidine 



H^N^ /NH2 



+ C— NH— (CH,);,— NH— C + 



Diguanidines 



+ /NH2 



H3N— (CHs).— NH-C + 



Agmatine 



H^N^ /NH2 



+ C— S — (CHs)^— S-C- + 

 HgN^ NH2 



Diisothioureas 



H2N /NH2 



+ C-NH — (CH2)4— NH-C + 

 HgN^ NH2 



Arcaine 



to indicate the equivalence of the C — N bonds and the states of the amino 

 groups, since there is resonance between forms such as the following for 

 the guanidinium ion: 



+ /NH2 



H,N— C 



+ 

 NH, 



^NH, 



H,N-C, 



,NH, 



NH, 



+ ^ 



Alkyl substitution does not reduce the resonance appreciably. 



Aliphatic monoamines, such as amylamine, are not substrates nor are 



