However, pharmacological action of the B-carbolines unrelated 
to monoamineoxidase inhibition has also been proven to exist 
(Schievelben er al. 1966). Further botanical and chemical studies 
are obviously needed to see if the two groups of compounds in the 
snuff are derived from one plant or a mixture of plants” 
(Holmstedt and Lindgren 1967). 
This observation has been often quoted and even misquoted. 
Additional phytochemical and enzymatic evidence is now 
available. Trace amounts of B-carbolines have been found to be 
present in Virola calophylla, V. theiodora and V. elongata (Fig. 
2). In one species, which is not known to be used hallucino- 
genically, Virola cuspidata, harman bases have been found to be 
the main alkaloids (Fig. 3) (Cassady er al. 1971). Their existence 
has been unequivocally proven by isolation, spectroscopy and 
mass spectrometry, as compared to synthetic reference com- 
pounds. Interestingly, these authors have also observed aroma- 
tization due to heat treatment such as that practiced by the 
Indians when preparing snuff from other species. They also point 
out the possibility of increased potency of enzyme inhibition due 
to the aromatization. 
Although the monoamineoxidase (MAO) inhibiting properties 
of harmine were observed indirectly before the enzyme was 
known to exist (Marinesco er al. 1930), it was only through 
Udenfriend and co-workers (1958) that these properties of the 
harmala alkaloids could be quantitated. Recently, the structure- 
activity relationship has been worked out for a large number of 
B-carbolines (Buckholtz and Boggan 1977). From this work, it is 
clear that the B-carbolines contained in Banisteriopsis Caapi and 
Peganum Harmala are far superior MAO-inhibitors than the 
compounds contained in usually trace amounts in Virola (Figs. 
2-3). Table 2 (from Buckholtz and Boggan) gives a comparison of 
enzyme inhibitory power. 
The occurrence of trace amounts of 6-methoxy-B-carbolines 
in some species of Virola (Table | and Fig. 2) is not surprising. It 
might be expected from the point of view of biosynthesis and 
workup procedure and is pharmacologically of no importance. 
The occurrence of a mixture of simple methylated indoles and 
harmine in one Indian snuff of unknown origin, or of harmine 
228 
