arkallic
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Synthesis of Serotonin
I've been wanting to do a synthesis of Serotonin for awhile now just because it sounds fun/cool to do. The best way I can find is decarboxylation of
5-HTP.
I found a process for the decarboxylation of l-tryptophan on the rhodium archives that uses copper(II)acetate to make Tryptophan Copper Chelate. Then
DMSO is added with heat, made basic with 30% NaOH, and extracted with chloroform. The process doesn't seem too hard and the chemicals not hard to get.
I asked my chemistry teacher if this process would work with 5-HTP and he said it should work fine. The only problem is that the process talks about
doing flash chromatography and I don't have the stuff to do that.
So here are my questions
1: Do I really need to do flash chromatography?
2: Could I replace chloroform with dichloromethane? If I had to guess it should work just as well. But I figure I should ask.
and 3: Is there a better way?
Thanks in advance!
[Edited on 7-3-2014 by arkallic]
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thesmug
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Sorry I have nothing to contribute but wouldn't this go in biochemistry?
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Crowfjord
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Chloroform is miscible with DMSO, according to this table, so that wouldn't work. Dichloromethane is not on there, but I imagine that it is soluble also. That's the problem with doing syntheses
in DMSO - it dissolves so many different solvents, making extraction difficult. The high boiling point makes distilling it off a pain, also.
My advice would be to try a ketone catalyzed decarboxylation in mineral oil, or tetraline, or naphthalene (see tryptophan decarboxylation thread in
Organic Chemistry subforum). Since serotonin has that hydroxy group, the purification would be a little different from that of tryptamine. Probably
careful pH control would be warranted - one needs to basify enough to get to the free amine, but keep the pH low enough to keep the aromatic hydroxyl
protonated.
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arkallic
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Thanks for the heads up on DMSO, I'll have to keep that in mind because it really does sound like a pain to deal with. I'll do some searching around
on ketone catalyzed decarboxylation and look at the post youre talking about. As for pH control that shouldn't be much of a problem since I have a
nice pH meter. Thanks a lot for your advice! If you or anyone else has some extra advice on the purification and the decarboxylation it would be very
much appreciated! I find all of this highly interesting and I'm excited to learn more. I think Serotonin is a really interesting compound  Heck, I find most tryptamines interesting.
[Edited on 8-3-2014 by arkallic]
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arkallic
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So I've done some reading up on ketone catalyzed decarboxylation from around the internet and looked at the post your talking about. I think I got the
decarboxylation process down and know what to do so thanks for that. It seems that mineral oil should work pretty well. But when it comes to the
purification process I'm still trying to figure out what exactly to do, I figure I'll take that on once I get to that point and try a few things out.
But I do have a question about naphthalene. If you where to distill it would naphthalene be dangers? (The only opening in my distillation setup is the
vacuum take off adapter) Would it require a fume hood or can I just do it outside?
Thanks!
[Edited on 13-3-2014 by arkallic]
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smaerd
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Add sufficient water to your DMSO during 'basification'. Should be able to do pulls with chloroform. Do a dry-run before though just to be sure but
I'll bet there will be no issues other then your chloroform will need several water washes.
Again that hydroxy will cause you trouble as it's a phenol moeity. Make sure you use an inert atmosphere. Zwitterions aren't the easiest thing to deal
with. Might be better off acetylating it or something similar to make work-up more straight forward. Not sure if the copper chelate will have any
affinity for the 'phenol' group.
[Edited on 13-3-2014 by smaerd]
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turd
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Quote: Originally posted by arkallic  | | I found a process for the decarboxylation of l-tryptophan on the rhodium archives that uses copper(II)acetate to make Tryptophan Copper Chelate.
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You chose - dead on target - the worst tryptophan decarboxylation method on Rhodium's. Cleaning tryptamines is difficult enough, why would you choose
a method that gives >50% trash to start with?
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