Phenethylamines Found in Plants

Phenethylamine, isolated in many instances from the putrefactive decomposition products of proteins (cf. Guggenheim (6)), occurs also as 

AT-Methyl-jS-phenethylamine occurs together with dipterine N-methyltryptamine) and leptocladine (3 4-dimethyl-3 4 5 6-tetrahydro- 

Halostachine was discovered by Yu. I. Syrneva (18) in the Chenopodiaceae Halostachys caspica C. A. Mey. The erroneously assigned molecular structure, C6H6 CH(NH-CH3)CH20H, was later corrected by G. P. Menshikov and M. N. Rubinstein (19) to C8H6-CH(OH)CH2NH-CHa. 

Halostachine is oxidized to benzoic acid by permanganate. It reacts with thionylchloride giving CeHiaNCl-HCl, m.p. 168-169 (from alcohol) JV-methylhalostachine yields with thionylchloride CioHhNCI--HCl, m.p. 202-203 . This compound is reduced by sodium amalgam to the base CioHuN (identical with AT-dimethyl-/3-phenethylamine), b.p. 

203-205 (picrate, from alcohol, m.p. 133-134°). Halostachine has thus the structure C,H5-CH(OH)CH2NH-CH3. 

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