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5-MeO-DMT
by Lester Grinspoon & James B. Bakalar
from Psychedelic Drugs Reconsidered
Other tryptamines supply the active components of several South American psychedelic snuffs and drinks. The chief of these is 5-methoxy-N,N-dimethyltryptamines (5-MeO-DMT).

It resembles DMT (see p. 19) in its effects, and is produced, along with other active tryptamines, by the trees Virola calophylla, Virola calophylloidea, Virola theiodora, Anadenanthera peregrina (Piptadenia peregrina), Psychotria viridis, and others. From the bark resin of the Virola trees Indians make a snuff called yakee or yako in Colombia and epena or parica in Brazil. From the seeds of Anadenanthera peragrina they make another snuff called yopo or parica in the valley of the Orinoco and cohoba in the West Indies; vilca or cebil, a snuff preparaed from the seeds of Anadenanthera colubrina, was formerly used in southern South America. Bufotenine (5-hydroxy-N,N-dimethyltryptamine, a better-known substance produced by some of the same plants as well as in the skin of toads, is not clearly psychoactive, apparently because it does not pass the barrier between the bloodstream and the brain; 5-methyoxy-N,N-DMT itself is about as potent as psilocybin but inactive orally. Harmala alkaloids have also been extracted from Virola resin; they allow the tryptamines to take effect orally by acting as inhibitors of the enzyme monoamine oxidase (MAOIs), which would otherwise destroy them. Several hydroxytrapptamine derivatives have strong effects on animals but are untested in man1.

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1 For further information see Brimblecombe and Pinder 1975, p. 108, p. 112, and the table on p. 117; see also Gillin et al. 1976.