1 8 THE SIMPLER NATURAL BASES 



case at least, a confusion with phenyl-ethylamine seems completely ex- 

 cluded. Compare further the section on p. 48. 



Phenyl-ethylamine does not accompany phenyl-alanine in seedlings 

 (Schulze [1906]), but with regard to the higher plants it should be 

 mentioned that Le Prince [1907] has isolated a volatile base C 8 H n N 

 from the European mistletoe (Viscum album} and that Crawford 

 [1911] attributes the pressor action of the U.S.P. extract of the 

 American mistletoe (Phoradendron flavescens) to the presence of abase, 

 C 7 H U N or C 8 H U N, which he thinks is perhaps identical with phenyl- 

 ethylamine. This base requires further investigation ; the presence of 

 phenyl-ethylamine may possibly depend on the fact that the mistletoe 

 is a semi-parasite. Although phenyl-ethylamine has not been found in 

 any fresh fungus, Reuter [1912] obtained it from Boletus edulis by 

 aseptic autolysis. Derivatives of phenyl-ethylamine have been found 

 in various essential oils ; thus phenyl-ethyl-alcohol 



C 6 H 5 .CH 2 .CH 2 OH 



occurs in rose oil and is also produced from phenyl-ethylamine by 

 yeast (Ehrlich); phenyl-acetonitrile, C 6 H 5 . CH 2 . CN, was found by Hof- 

 mann [1874] in the essential oil of Nasturtium officinale^ and phenyl- 

 ethyl-z'jtf-thiocyanate is present in the oil from the root of Reseda 

 according to Bertram and Walbaum [1894], and yields phenyl-ethyl- 

 amine on hydrolysis. Possibly phenyl-ethylamine is an intermediate 

 stage in the formation of all three substances from phenyl-alanine. 



p-Hydroxy-phenyl-ethylamine, OH . C 6 H, . CH 2 . CH 2 . NH 2 . 



This amine was first obtained by Schmitt and Nasse [1865] by 

 heating tyrosine, when the following change occurs : 



HO/ \CH 2 . CH (NH 2 ) COOH = HO/'" ~\CH 2 . CH 2 . NH 2 + CO 2 . 



p-Hydroxy-phenyl-ethylamine was subsequently isolated from auto- 

 lysed pancreas by Emerson [1901] and from a prolonged peptic 

 digestion of egg-albumin by Langstein [1901, 1902]. It seems pretty 

 certain that in these experiments bacterial action was not completely 

 excluded (see p. 10). Gautier and Mourgues [1888] isolated the base 

 from the mother liquors obtained in the putrefaction of cod-livers 

 (in the old process of making cod-liver oil). Gautier also obtained in 

 small quantity a lower homologue C 7 H 7 NO and a higher one 

 C 9 H U NO and named the three bases " tyrosamines ". The last two 

 do not, however, appear to have been sufficiently well characterised. 

 p-Hydroxy-phenyl-ethylamine is fairly abundant in various kinds 

 of cheese. It was found by Van Slyke and Hart [1903] in Cheddar 



