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blunts
(Stranger) 08-13-03 07:57 No 453254 |
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4-methoxy indole to 4-ho-dmt | ||||||
swim was wondering if its possible/feasable to get some psilocybin from 4-meo-indole. sorry swim doesnt have too much chemistry experience (classes start in a few weeks :)) any help or info would be appreciated |
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Rhodium (Chief Bee) 08-13-03 14:27 No 453303 |
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4-MeO-Indole demethylation | ||||||
I think 4-MeO-Indole derivatives can be demethylated using buffered boron tribromide, but I'm not sure. I can say as much as it is not an easy transformation. |
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blunts (Stranger) 08-14-03 07:47 No 453476 |
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what else.. | ||||||
anyone know what else 4-methoxy indole could be used as a precursor for? |
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Rhodium (Chief Bee) 08-14-03 12:24 No 453507 |
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Any 4-Methoxy-tryptamine, such as 4-MeO-MIPT | ||||||
Any 4-Methoxy-tryptamine, such as 4-MeO-MIPT (http://www.erowid.org/library/books_onl |
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pHarmacist (pHantasticant) 08-22-03 14:43 No 455025 |
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de-O-methylation | ||||||
swim was wondering if its possible/feasable to get some psilocybin from 4-meo-indole. There is an old route to Serotonin where they preform de-O-methylation using AlCl3. For experimental details turn your attention to: Abramovich, R. A and Shapiro, D., J. Chem. Soc., 1956, 4589; Henecka, H., Timmler, H., Lorenz, R., and Geiger, W., Chem.Ber., 1957, 90, 1060 I can't see why they start with p-methoxy-phenylhydrazone, a number of other counterparts that are easier to get rid of would give better yield in the last step.. Do NOT disturb: Mind at Large |
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Rhodium (Chief Bee) 08-22-03 20:11 No 455051 |
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O-protection | ||||||
What O-protection groups (avaliable in the fifties), which also survives the initial aniline diazotization to the phenylhydrazine, followed by the Fischer Indole Synthesis, can you think of? There is always benzyl, but maybe they didn't have access to high-pressure catalytic hydrogenation in that lab (CTH wasn't invented yet). |
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Rhodium (Chief Bee) 08-22-03 22:23 No 455063 |
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The Discovery of Catalytic Transfer Hydrogenation (Rated as: excellent) |
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Well, the first Catalytic Transfer Hydrogenation was reported in the literature only 50 years ago: ![]() ![]() ![]() ![]() ![]() ![]() ![]() ![]() ![]() Cited from: Catalytic Transfer Hydrogenation (Review) Gottfried Brieger, Terry J. Nestrick Chem. Rev. 74, 567-580 (1974) (../rhodium/pdf /cth.review.p Edit: Hmm, it seems like the question I answered disappeared meanwhile... Oh well, it doesn't matter, this is interesting anyway ![]() Also, here is a related review article of interest: Heterogeneous Catalytic Transfer Hydrogenation (Review) R.A.W. Johnstone, A.H. Wilby, I.D. Entwistle Chem. Rev. 85, 129-170 (1985) (../rhodium/pdf /heterogenous |
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pHarmacist (pHantasticant) 08-22-03 22:26 No 455064 |
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Great... | ||||||
Thanks for the info. I deleted my post as I thought no one would answer my question... EDIT: The question was: "Oh, no kidding, so when did CTH came about?" Do NOT disturb: Mind at Large |
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pHarmacist (pHantasticant) 08-29-03 09:57 No 456318 |
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hey, blunts | ||||||
See the last step (Scheme 1): Post 456207 (pHarmacist: "Labelled indolealkylamines for brain mapping", Tryptamine Chemistry) Good luck! Point... Counter Point... |
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