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The cactus genus Coryphantha has been reported to contain certain β-phenethylamine alkaloids. In this investigation, a Texas species, C. ramillosa Cutak, yielded five alkaloids which were isolated chromatographically and crystallized as their hydro-chloride salts. The isolated compounds were identified as N-methyl-4-methoxy-β-phenethylamine hydrochloride, hordenine hydrochloride, N-methyltyramine hydrochloride, synephrine hydrochloride, and β-O-methylsynephrine hydrochloride, all of which have been previously identified in other Coryphantha species.

The presence of alkaloids was chromatographically demonstrated in seven species of Coryphantha. By using preparative chromatographic techniques, N-methyl-3,4-dimethoxy-β-phenethylamine, N-methyl-4-methoxy-β-phenethylamine, N-methyltyramine, and N,N-dimethyltyramine (hordenine) were isolated from extracts of C. cornifera (DC.) Br. and R. var. echinus (Engelm.) L. Benson. In addition, two new cactus alkaloids, N-methyl-4-hydroxy-β-methoxy-β-phenethylamine (β-O-methylsynephrine) and 4-methoxy-β-hydroxy-β-phenethylamine, were identified spectroscopically in extracts of this species.

Hordenine HCl and N-methyltyramine HCl were crystallized from extracts of the cactus Ariocarpus kotschoubeyanus (Lemaire) Schumann. Other alkaloids, which have been found in closely related Ariocarpus species, were not detected in this species. Extraction of the isolated alkaloids by percolation gave higher yields than continuous extraction.

Eleven β-phenethylamine derivatives were isolated and identified from fresh-frozen specimens of Coryphantha macromeris var. runyonii (Br. and R.) L. Benson. Isolations were accomplished using preparative TLC, and identifications were based on chromato-graphic properties, IR and NMR spectra, and comparisons with authentic materials. The data provide initial documentation for: the occurrence of N-formylnormacromerine in nature; the first recorded detection of metanephrine and N-methylmetanephrine in the plant kingdom; the first occurrence of synephrine and N-methyltyramine in this cactus; confirmation of earlier GLC-mass spectral data on the presence of N-methyl-4-methoxy-β-phenethyl-amine, N-methyl-3,4-dimethoxy-β-phenethylamine, tyramine, and hordenine in the plant; and verification of previous reports on the isolation of macromerine and normacromerine.

Macromerine, a β -phenethylamine alkaloid previously isolated from Coryphantha macromeris , has been isolated from Coryphantha runyonti .

Ariocarpus fissuratus var. fissuratus (Engelmann) K. Schumann, commonly known as living rock, chaute, peyote, sunami, or dry whiskey, has an interesting history of folkloric medicinal uses. In previous phytochemical studies the alkaloids, hordenine and N-methyltyramine, have been identified in both the fissuratus and lloydii varieties of the species. In the present investigation, a new alkaloid was crystallized from the nonphenolic alkaloid fractions and identified as N-methyl-3,4-dimethoxy-β-phenethylamine HCl. This compound has previously been reported in three other cactus species.