December 05, 2021, 08:36:48 AM
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Topic: Synthesizing Serotonin from 5-HTP artificially  (Read 170 times)

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Offline joon

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Synthesizing Serotonin from 5-HTP artificially
« on: November 18, 2021, 05:42:58 PM »
So I would like try and do this synthesis because I kind of like the idea of creating a neurotransmitter from pretty widely available supplement. I of course know that there wouldn't really be a use for that serotonin, but I kinda just want to do this, because it seems interesting.
I don't how hard this synthesis will be, it is an decarboxylation, it kinda seems not to extremely hard but at the same time I feel like it will be very hard, especially for me, who does not have a lot of practical experience with organic chemistry.

As far as I understand, a decarboxylation kind of needs heat, but just throwing some 5-HTP in a microwave and calling it a day would most likely not succeed.
My current idea disolve 5-HTP into acetophenone, which will act as solvent and as a catalyst at the same time, because as far as I know ketones would catalyse this kind of reaction. After refluxing it for some time, I would distill of the acetophenone. After distillation I would disolve the serotonin, which should have formed while refluxing the acetophenone - 5-HTP solution, with weak hydrochloric acid. After it's disolved in the hydrochlorid I would freebase it again with a strong sodiumhydroxid solution. Then I would disolve the freebase into some acetone and then try to crystalize the serotonin. While refluxing I will have to monitor the CO2 production somehow, because CO2 forms in decarboxylations, and if the production of CO2 stops the reaction should be done.

That is my current idea, but I am kind of doubting this would work for some reasons:
1. I don't know the temperature at which serotonin degrades, I couldn't find it. So I might have the problem, that my serotonin is destroyed while distilling the acetophenone of, because the boiling point of acetophenone is 202°C
2. I've adapted this from researching how to do a tryptophan decarboxylation, because I couldn't find that for 5-HTP decarboxylation and Tryptophan and 5-HTP are quite similar, with the difference being a hydroxyl group. And for the tryptophan decarboxylation, I've read that there might be a problem with aqueous HCl destroying the product. I don't know if that is a thing, and if it is a thing if it would be on a scale I would care much about, because I am not ingesting it or anything, I would maybe just try and melt it to see if it has a melting point close enough to pure serotonin.
3. As I've stated above, I am not that experienced with organic chemistry, even though I am interested in it. I have a feeling this might just be above my level and that I am overestimating myself. I would probably try it anyway though, because I am not really expect success on first try anyway and I would like to try.

I would apreciate if you know the thermal degradation point of serotonin, on the hydrochloric acid thing, or any thought on this in generell.


Offline Babcock_Hall

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Re: Synthesizing Serotonin from 5-HTP artificially
« Reply #1 on: November 19, 2021, 10:03:25 AM »
Under conditions needed to hydrolyze a peptide bond (6 M HCl, 110 °C), tryptophan is decomposed.  I am not sure of the exact conditions where this decomposition becomes insignificant.

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