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Agurell S, Holmstedt B, Lindgren JE, Schultes RE. 
“Alkaloids in certain species of Virola and other South American plants of ethnopharmacologic interest”. 
Acta Chem Scand. 1969;23(3):903-16.
Virola theiodora, a botanical source of intoxication snuffs used by certain South America Indian tribes, has been shown to contain the hallucinogen 5-methoxy-N,N-dimethyltryptamine as well as a number of other indoles. One Indian snuff proved to be unusually high in alkaloid content (11%). Considerable differences in the alkaloid composition of different parts of single plants were encountered, N,N-dimethyltryptamine being the major component in the leaves and 5-methoxy-N,N-dimethyltryptamine in the bark of Virola theiodora. Of other species of Virola investigated V. rufula contained substantial amounts of tryptamines, whereas V. multinervia and V. venosa were almost devoid of alkaloids. V. calophylla contained high amounts of alkaloids only in the leaves. Two new β-carbolines of a type carrying the substituents in the 6-position of the β-carboline nucleus were found in V.theiodora, V. rufula, and Anadenanthera (Piptadenia) peregrina. By spectrometric and other data their structures have been shown to be 2-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline and 1,2-dimethyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline.
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