5-methoxy-DMT

Compounds with a low relative activity (e.g., DMT, DET, 5 methoxy-DMT) have very little activity orally and must be smoked or sniffed. Unfortunately, these compounds taste and smell like burning plastic when smoked and are harder to smoke than hash. There is, however, no evidence for the notion that they are damaging. With the exception of DMT, DET, psilocin and psilocybin, most of these compounds are probably legal in most states. 

The effects of 5-methoxy-DMT are unpleasant for most people (smoking it gives me nausea plus the feeling that I m being sat on by an elephant), but it is not known whether other substituents in the 5 position or in the 4 and 5 positions simultaneously will be similarly distressing. 

Illustrated for 5-methoxy-tryptamine (1). 1.5 g (1), 30 ml ethanol add 5 g methyl iodide (or equimoiar amount ethyl iodide) and 4.5 g dry sodium carbonate and heat five hours on water bath. Filter hot, heat precipitate with ethanol and filter hot again. Evaporate in vacuum to get 2.5 g l-methyl-5-methoxy-DMT. 

Dissolve 35 g 5-methoxy-DMT (or analog) in 100 ml glacial acetic acid, cool to 10°, stir and add dropwise a solution of 30 ml concentrated HN03 in 50 ml glacial acetic acid over one-half hour. Let warm to room temperature, stir eight hours and dilute with 1 L ice-water. Filter, wash precipitate with water and dry to get 4.5 g 5-methoxy-4-N 02-DMT (recrystallize-methanol). 

A true academic challenge exists with the many studies of 5-methoxy-DMT (as has been mentioned under DMT, different drug, same problem) which have involved drug mixtures. The second drug, added to the tryptamine, is almost... 

The first European observation of psychedelics-use in the New World involved cohoba snuff, a powerful mind-alterer made from seeds of theyopo tree Anadenantheraperegrina). The main psychoactive components were identified in the early 1950s as DMT (N,N-dimethyltryptamine) and 5-methoxy-DMT. These and related compounds are present in other trees, vines and shrubs and even in mushrooms. 

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. 

DPT and 5-methoxy-DMT are still legal and have been used in certain circles for years. Alan Birnbaum, from the Native American Church of New York, wrote to the DEA about the legal status of several DMT-Iike compounds. In January 1980, Howard McClain of the Regulatory Control Division responded ... 

In both Anadenanthera and Virola snuffs, the active principles are indolic alkaloids, either "open-chained or "closed-ring tryptamines. The "closed-ring group will be covered in the next chapter. The "open-chained group includes DMT and 5-methoxy-DMT, as well as bufotenine (which at present appears to be non-psychoactive). DMT predominates in the species Virola calophylla, but in other species the greatest psychic contribution comes from the very short-acting 5-methoxy-DMT. 

Long available from chemical supply houses, 5-methoxy-DMT is about five times as strong as DMT when smoked and the shortest-acting of all these compounds. The experience is characterized by a "rush similar to that from amyl nitrate. There is little in the way of visuals, but intense thoughts and perhaps bodily sensations last for five to ten minutes. Many people don t like it in his Psychedelic Chemistry, Michael Valentine Smith compares its effects to having an elephant sit on one s head. 

Christian et al. refers to Dr. Samuel Christian and his associates at the University of Alabama in Birmingham s Neurosciences Program in 1975 they identified DMT, 5-methoxy-DMT, 5-methoxy-N,N-DMT, N-methyltryptamine and tryptamine in human cerebrospinal fluid. In May 1977, Dr. Wolfgang Vogel of the Jefferson Medical College in Philadelphia isolated 5-methoxy-DMT in brain tissue the Christian team also found DMT there. 

If DMT and 5-methoxy-DMT are neurotransmitters, as many researchers think, then an excess of them may be a cause of schizophrenia. Observing dramatic increases of DMT in the spinal fluid of animals and humans "during extreme stress," Dr. Christian hypothesized that the tendency among some people to develop mental aberrations might reflect "a genetic predisposition to excessive DMT production as a response to stress. Later work, reported by L. Corbett, Christian and others in the British Journal of Psychiatry (1978, 132 139-144), indicated that schizophrenics do not have higher levels of DMT in their brains than control subjects. Research in this intriguing area continues. 

At a 1977 conference in San Francisco, Bo Holmstedt, a pioneer in research on harmala alkaloids from the Karolinska Institutet in Sweden, suggested that similar substrates and enzymes are in the pineal gland for endogenous production of DMT, 5-methoxy-DMT and the N-methyl analogues of harmine and harmaline. Brimblecombe and Pinder, in their Hallucinogenic Agents (p. 116), discuss possible metabolism routes by... 

If a methoxy molecule (instead of hydroxy) is substituted at the 5-position with DMT, we have 5-methoxy-DMT, or 5-meo-DMT, a substance as equally powerful as DMT, but more potent, i.e., the same effect is produced by a much smaller dose. This tryptamine derivative is the main psychoactive ingredient in shamanic snuffs, variously known as cohoba, yopo, epena, and other names, derived from two South American plant sources. These snuff materials have a long documented... 

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