Virolas

Myristic acid occurs as a glyceride in many vegetable fats and oils, in particular in coconut oil,i its isolation from which involves separation from homologs by fractional distillation of the acids or their esters. The trimyristin obtained from nutmegs 2 (p. 100) or from the seeds of Virola venezuelensis forms the most suitable source. 

Such alkaloids are N, N-dimethyl tryptamine, 5-methoxy-N, N-dimethyl trypta-mine, and 2-methyl-1, 2, 3, 4-tetrahydro-fJ-carboline, which have been characterized from the resins of several Virola species, which is used by the witch doctors of several... 

Oo-koo-he is made from the resin of certain trees of the Myris-ticaceous genus Virola mixed with the ashes of other plants and rolled into pellets and swallowed. What was eye-catching about the description of this visionary plant preparation was that the Witoto tribe of the Upper Amazon, who alone knew the secret of making it, used it to talk to "little men" and to gain knowledge from them. 

Doctor, our apologies for disturbing your solitude and the local social environment here. We can appreciate your wish to be undisturbed in your work. We are anxious to push on to La Chorrera, and we hope that you will help us arrange bearers here to go with us. Also, we are here with a special purpose. I refer to the Virola hallucinogens that you reported to Schultes."... 

Schultes, R. E. "Virola as an Orally Administered Hallucinogen." In the Botanical Museum Leaflets of Harvard University, vol. 11 no. 6, pp. 229-40. 

Eb6na Virola theiodora Inner bark Several tryptamines, including the most potent hallucinogen known from nature 5-methoxy-N,N-dimethyltryptamine Snuff Hallucinogenic Yamomami Amazon basin... 

Plants containing indoleamines include Psilocybe mushrooms, morning glory and Virola. Plants containing tropane alkaloids such as the muscarinic antagonists scopolamine and atropine are found in some members of the Solanaceae plant family—including datura, mandrake, henbane and... 

Carvalho, J.C.T. et al.. Anti-inflammatory activity of flavone and some of its derivatives from Virola michelli Heckel, J. Ethnopharmcol, 64, 173, 1999. 

Lopes, N.P., Kato, M.J., and Yoshida, M., Antifungal constituents from roots of Virola surina-mensis. Phytochemistry, 51, 29, 1999. 

DMT is found in the South American plants Virola calophylla and Mimosa hostilis, and in grasses, mushrooms, toads, grubs, and fish, and has been used by the Amazon natives for spiritual effects. DMT was synthesized in 1931. 

EXTENSIONS AND COMMENTARY N-Methyltryptamine (monomethyltryptamine, NMT) is an alkaloid that has been found in the bark, shoots and leaves of several species of Virola, Acacia and Mimosa. However, the major snuffs associated with these plant have been shown to also contain 5-MeO-DMT and are discussed there. NMT has been synthesized in a number of ways. One can react 3-(2-bromoethyl)indole with methylamine. NMT can be isolated as the benzoyl derivative from the methylation of tryptamine with methyl iodide followed by reaction with benzoyl chloride, with the hydrolysis of this amide with alcoholic KOH. It can also be synthesized from indole with oxalyl chloride, with the resulting glyoxyl chloride reacting with methylamine in ether to give indol-3-yl N-methylglyoxalylamide (mp 223-224 °C from IPA) which is obtained in a 68% yield, which is reduced to NMT to give the amine hydrochloride (mp 175-177 °C from ) in a 75% yield. The most simple and direct synthesis is the formamide reduction given above. 

Members of (he family contain many substances of possible interest as bioactive compounds, but the tryptamines of species of Amazonian Virola have had special attention for their hallucinogenic effects. 

Virola calophylla, V callophylloidea, Virola spp. (3/4), V surin-amensis. 

DMT, or N,N-dimethyltryptamine, is a hallucinogenic chemical found in a variety of natural and synthetic compounds. It is present in many plant genera Acacia, Anadenanthera, Mimosa, Piptadenia, Virola) and is a major component of several hallucinogenic snuffs (cohoba, parica, yopo). DMT is also present in the intoxicating beverage ayahuasca, which is made from Banis-teriopsis caapi plants. 

Virola genus, including V. theiodora, V. calophylla, V calophylloidea, V. surinamensis, V. cuspidata, V. elongata, V. lorentensis, V. peruviana, V. rufula, and V. sebifera... 

EPENA -- Also called yopo. Virola calophylla. Family Myristicaceae (Nutmeg family). 

Material Indole-based alkaloid found in seeds, pods, bark, and resins of several South American trees, including Piptadenia peregrina and Virola calophylla, used in the snuffs yopo, epena, and parica. 

Anadenanthera Species and Other Members of the Pea Family, 316 Virolas, 317... 

Inner bark from the tree represented here by its leaves is the main species of Virolas used by South A merican natives as a source of psychoactive tryptamines. 

In 1954, Stomberg isolated 5-methoxy-DMT from seeds of A. pere-grina. Later, DMT, DMT-N-oxide and 5-hydroxy-DMT-N-oxide were also found in A. peregrma. Additional components contributing to psychoactivity have been identified these also appear in about the same proportions in the Virola species used to make paricd. However, a Waikd snuff made from V. theiodora resin has an unusually high alkaloid content of up to 11 percent, consisting mainly of 5-methoxy-DMT (8 percent) and substantial amounts of DMT. 

DMT-like compounds appear in the sap of the inner bark—not in the seeds or roots of Virolas. The making of epena therefore involves stripping Virolas of their outer bark. An almost colorless liquid then exudes from the inner bark, quickly turning to blood red (the result of enzyme activity) and... 

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