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5-MeO-DMT Information
by Jonathan Ott
from Pharmacotheon
Like DMT, this drug is evidently not active orally. Smoked it is about four times the potency of DMT. Shulgin conducted experiments with nine subjects, finding that smoking 6-10 mg of the free base of 5-MeO-DMT produced an entheogenic effect starting in less than 60 seconds, reaching a peak in two to three minutes and lasting about twenty minutes (Shulgin in DeSmet 1983). Shulgin had earlier reported the 5-10 mg of 5-MeO-DMT was active by parenteral injection (Shulgin 1970). In combination with MAO-inhibitors, 5-MeO-DMT is active orally at a dose of 10 mg (Callaway 1992). While Jeremy Bigwood and I once commented that 5-MeO-DMT had "little recreational value" (Bigwood & Ott 1977) and M.V. Smith compared the effects of this drug to having a large elephant sit on one's head (Smith 1976), nevertheless it has its adherents, and recently a modern ritual cult has grown up around the "Toad of Light," Bufo alvarius, whose toxin contains principally 5-MeO-DMT. As mentioned above, adherents of the "Church of the Toad of Light" collect and dry the venom of this toad for smoking as a sacrament (Davis & Weil 1992; Krajick 1992; Most 1984). The asymmetrical isopropyl analogue of 5-MeO-DMT, 5-methoxy-N-methyl-N-isopropyltryptamine (5-MeO-MIPT) is active orally at a 5 mg dose, but like the DMT analogue MIPT produces amphetamine like stimulation and not entheogenic effects (Repke et al. 1985).

Examination of snuff preparations found DMT, bufotenine and 5-MeO-DMT in yopo snuff from Colombia, and the same compounds plus harmine in a snuff prepared from A. peregrina by Piaroa Indians of the Orinoco basin (Holmstedt & Lindgren 1967).

[...]

Numerous species of Virola have been studied chemically, and the bark from which the snuffs are prepared contains chiefly DMT and 5-MeO-DMT as entheogenic principles (Agurell et al. 1969; Holmstedt 1965; Holmstedt et al. 1980; McKenna et al. 1984b), although tryptamine, N-monomethyltryptamine (MMT or NMT), 5-methoxy-N-monomethyltrytamine (5-MeO-MMT), and 2-methyl-1,2,3,4-tetrahydro-B-carboline (MTHC) have also been found in bark and bark exudates (Holmstedt et al. 1980). Bark of V. sebifera, reportedly smoked in Venezuela, has been shown to contain DMT, 5-MeO-DMT and MMT (Corothie & Nakano 1969; McKenna et al. 1984b). Tryptamines, principally DMT, have been found in leaves, roots and shoots of Virola species, with 4-MeO-DMT, MMT and 6-MeO-DMT being also prominent constituents of some species (Holmstedt et al. 1980). The usually small quantities of Beta-carbolines detected in Viorola species by Agurell's and Holmstedt's groups were not confirmed in analyses of bark and leaf samples of various Virola species in subsequent work (McKenna & Towers 1985; McKenna et al. 1984b). The following Virola species have been found to contain tryptamines: V. calophylla, V. calophylloidea, V. carinata, V. divergens, V. elongata, V. melinonii, V. multinervia, V. peruviana, V. pavonis, V. rufula, V. sebifera, V. theiodora and V. venosa (Holmstedt et al. 1980; McKenna et al. 1984b).

Chemical analysis of four specimens of epena found 5-MeO-DMT to be the main components in three preparations (made by the Tukano, Waika and Araraibo Indians of Brazil and Venezuela), followed by DMT in all of the snuffs. The Tukano snuff contained also 5-Me)-MMT, and the Waika snuff contained MMT.

[...]

A Brazilian epena snuff prepared from Virola theiodora was found to contain principally 5-MeO-DMT, with lesser amounts of DMT, MMT, 2-methyl-tetrahydro-beta-carboline (MTHC) as well as its 6-methoxy derivative. A Brazilian nyakwana snuff prepared from the same species likewise contained principally 5-MeO-DMT, with lesser amounts of DMT, MMT, 5-MeO-MMT and 6-MeO-MTHC, a total of 11% alkaloids. It would appear that in general 5-MeO-DMT and DMT are the principal entheogenic constituents of epena and related snuffs. These compounds together with the inactive MMT, were recently found in several samples of Yanamamo snuffs from Venezuela (McKenna et al. 1984b).