Although melatonin is generally priced relatively high, does it have potential as a tryptamine precursor? I've seen at least one reference refering to using melatonin as a precursor to 5-Methoxy-Tryptamine.
Does anyone have any ideas if the syntheses above are easily accomplished? Is it even worth the time / effort?
Your drawings reminded me of the hydrolysis of N-formylamphetamine to give amphetamine, at least for the upper structure.... You can boil the formyl compound wit hydrochloric acid for 2 hours (under reflux) to give amphetamine.
Not sure though whether your methoxy group and nitrogen containing ring will survive. Methoxy may be OK, since you can make p-methoxyamphetamine with Leuckart as well.
42g melatonin taken up in 300g isobutanol. Add 30g NaOH and 3g sodium dithionite. Reflux 2h @ 105 deg. under N2. Cool mixt. ext with 500g water. Aqueous phase conatins sodium acetate and excess NaOH-seperate. Acidify isobutanol phase to pH 2 with 32% HCl. Concentrate solution to induce crystallization of 36g crude mexamine. Recrystallize from 96% EtOH to obtain 30g white crystalls of mexamine of 98.5% purity.
Reference: U.S. Patent 4,772,726
Mexamine is aka 5-Methoxy-Tryptamine.
I'd really like to know if there is any way to easily obtain 5-MeO-NMT from melatonin.
Vitriodor: the result of such a hydrolysis of melatonine is 5-MeO-trptamine.
Normally you could methylate primary amines through formylation, by refluxing with ethylformate, followed by HCl hydrolysis (a leuckart-variation), to give methylamino derivatives.
But in the case of tryptamines this doesn't work, because they cyclize into beta-hydrocarbolines when methylation with formaldehyde is attempted. ("pictet-spengler!" )
This is a well-known problem, and can be circumvented by using MeI or other methylating agents, or by protecting the formed secondary amine as a salt immediately post formation (I think )...
(check out TiHKaL....)
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