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Smoking Toad Venom Phenomenon: Hamilton's Pharmacopeia Season 3
ApeMaia:
First episode is out, an amazing story about Ken Nelson aka Albert Most, the person who first discovered in our modern era the psychoactive effects of 5-meo-DMT.
And there's a pretty neat video on the synth of the compound :)
h00ps://www.youtube.com/watch?v=fFXGa-Ruz_M&ab_channel=VICE
bubbles:
Cool! I was looking forward to the new season.
Edit: I just watched it and it is indeed a very good episode! I'm not gonna spoil it but I really like what he did for 5-meo-dmt culture.
loft:
Great to see the episodes being available for free. I hope this applies to the whole season!
FYI I attached the pages shown in the documentary added by Hamilton Morris. Did anyone find a place to buy this reissued pamphlet?
bubbles:
https://www.psychedelictoadofthesonorandesert.com/
Not working yet but should be later today according to Hamilton.
loft:
I wonder why Hamilton cited He and Xi (https://sci-hub.st/https://www.sciencedirect.com/science/article/abs/pii/S0040403914008521), although they themselves referenced Bosch et al.'s paper as the origin for the reductive amination (https://sci-hub.st/https://www.sciencedirect.com/science/article/abs/pii/S0040402000010917).
Taken from Bosch et al.:
--- Quote ---3-[(2-Dimethylamino)ethyl]-5-(1-pyrrolidinylsulfonylmethyl)indole (9b). A solution of 35% formaldehyde (35 mL, 416 mmol) in MeOH (35 mL) and a solution of NaBH4 (5 g, 132 mmol) in H2O (70 mL) were added drop-wise, simultaneously, at 15°C to a well-stirred solution of tryptamine (8.1 g, 26 mmol) in MeOH (150 mL). The mixture was stirred at 15°C for 0.5 h, 2N aqueous HCl was cautiously added to bring the pH to 3, and the resulting mixture was stirred for 10 min. Then, the pH was adjusted to 6.5±7 with saturated aqueous NaHCO3, MeOH was evaporated, and H2O (50 mL) was added. The mixture was washed with EtOAc (2x 150 mL), basified with K2CO3, and extracted with EtOAc (2x 130 mL). The organic extracts were dried, filtered, and concentrated to give 9b (7.70 g, 88%) as a brown solid.
--- End quote ---
From He et al (Supplementary), a more closely related structure, DMT itself:
--- Quote ---DMT (9). A solution of 37% formaldehyde (147.0 ml, 2000.0 mmol) in MeOH (80.0 ml) and a solution of NaBH4 (23.6 g, 625.0 mmol) in H2O (210.0 ml) were added dropwise, simultaneously, at 15 °C to a well-stirred solution of tryptamine (20.0 g, 125.0 mmol) in MeOH (320.0 ml). The mixture was stirred at room temperature for 30 min. Then , the solution was adjusted to pH 9 by addition of 10% aqueous Na2CO3. MeOH was removed by distillation and the product was extracted with ethyl acetate (3×100 ml). Then the organic layer was washed with brine, dried over Na2SO4, concentrated under reduced pressure. The residue was recrystallized with ethyl acetate-hexane (5:1) to give 9 as a light brown solid (yield 21.2 g, 90.2%).
--- End quote ---
It's been a while since I looked at 1H NMR spectra but the one from DMT, synthesized as described above by He et al., is attached below.
Final edit to this post: I'm just writing down the CC from Hamilton's synthesis
--- Quote ---100 grams of 5-MeO-tryptamine freebase is dissolved in MeOH with vigorous magnetic stirring. A thermometer probe is inserted into the methanolic 5-MeO-tryptamine, and the solution is cooled until it nears 0 °C. Aq. KOH is used to dissolve and stabilize 100 grams of NaBH4, and the solution is transferred into an addition funnel. A second addition funnel is charged with a MeOH-stabilized aq. 37% formaldehyde solution, and the drop-wise addition begins. "And now I start adding the borohydride." [...] Borate salts gradually precipitate, and the salt volume is reduced by overnight heating. As the methanol evaporates, 5-MeO-DMT precipitates as a brown oil and coalesces on the surface. "Pretty beautiful." Simple distillation is used to strip the remaining water, followed by purification of the crude freebase via short path vacuum distillation, "We did it. Yes.", and recrystallization. [...] After TLC had shown total transformation of the starting material, LC-MS confirmed the product was 5-MeO-DMT.
--- End quote ---
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