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"Ariadne" aka "4C-D"; the only Shulgin child to almost become a medicine. Details + synthesis in comments
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Anyone subscribed to Hamilton Morris' patreon (if you are not yet, you should) may have learned more about them unusual pharmacology and history of this (non) psychedelic. Also called "4C-D", the alpha-ethyl homologue of DOM, "dimoxamine" as an almost-medication, etc.

This has been on my radar for some years, and I always imagined this compound to be a fabulous antidepressant, maybe even deliver the benefits which "microdosing" never actually did.

So I made some… I must say, this is a very pleasant and functional drug.. an improved adderall, sorta. Or as Sasha said; "The alert of a psychedelic, with none of the rest of the package."

If that doesn't compel you, I'll add that it made it to phase 2 clinical trials as a panacea med for a whole SLEW of ills, as it was found to produce: "rapid remission of psychotic symptoms in schizophrenics, relaxation in catatonics, complete remission of symptoms in Parkinson’s disease (PD), and improved cognition in geriatric subjects". (Dr. Mike Cunningham's findings on its pharmacology https://pubs.acs.org/doi/10.1021/acschemneuro.2c00597#)

Synthesis: Screwed up my ratios and foolishly lost some product, will post a more comprehensive write up when it's perfected… If anyone cares lol: -1mol equiv. 2,5-DM-4-MethylBA was condensed with -3mol equiv (too much, shoulda only used 1.5) 1-Nitropropane, distilled from fuel-additive. -Ethanolamine Acetate served as amine catalyst and solvent, with excess GAA to dissolve aldehyde. (This solvent/catalyst system yeilds stupid-high for nitropropenes, and apparently nitrobutenes too!) -Reacted for 6hrs at 60C and allowed to cool to RT. -2,5-dimethoxy-4-methyl-nitrobutene crystalized on top later as brilliant, fluffy orange crystals.

Unfortunately the excess of nitropropane and toluene which azeotropically distilled from the fuel-additive was difficult to remove without vacuum, and pulled product out, reducing yield.

Re-x, re-x, reduce w/ NaBH4/Cu , precipitate as HCl salt.. share some with your grandmother!

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1 year ago