Suppose SWIM had some aged bark, where most of the actives had degraded to n-oxides. Would acidifying it in a solution (as in a/b extraction, or ayahuasca-like preparation) pull any of them out?
The n-oxides are very soluble in water, more so than their parent compounds. DMT n-oxide is extremely water soluble. No need for any acid. But if doing an A/B, you can't use naphtha to extract DMT n-oxide. Xylene or d-Limonene would work better and DCM or chloroform would probably be the best non-polar solvents in this case.
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