spotlightman1234
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Extraction of 5-HTP and decarboxylation to serotonin?
Hey guys! Some time ago I was browsing rhodium when I stumbled upon a page showing different methods of decarboxylating tryptophan to obtain
tryptamine (see link below). In one of the procedures it was noted that the use of 5-hydroxytryptophan in place of tryptophan could potentially yield
5-hydroxytryptamine (serotonin). I really want to see if it is possible to synthesize serotonin this way, so... Recently I obtained a bottle of 30
100mg capsules of 5-HTP from my local super store (I attached a picture of the bottle I bought.). The capsules are clear gel caps and have a brown/tan
colored powder in them. The label listing the ingredients said that they contain 100mg 5-HTP, gelatin (capsules), rice flour, water, magnesium
stearate, and silica. I did some research and I found that ethanol would be a suitable solvent for dissolving out the 5-HTP from the powder in the
capsules, while minimally dissolving the flour, silica and magnesium stearate.
Here's what I have done so far:
Four 100mg 5-HTP capsules were opened and the brown/tan contents placed in to a 50ml erlenmeyer flask. ≈25ml of (≈95%) ethanol is poured
in to the flask. The slurry in the flask is gently heated just below boiling. A stir bar is placed in the flask and the flask stoppered, the
suspension is stirred for a few minutes. After stirring the flask is placed in the fridge and allowed to cool a little below room temp (≈15C).
The suspension settled out forming a grey/tan layer of insolubles on the bottom and a brown solution on top. The flask is swirled to bring solids back
in to suspension and the liquid is vacuum filtered, yielding a clear brown ethanol soln, and a grey/tan solid in the filter paper. The solid in the
filter paper is saved and the ethanol soln is allowed to evaporate at room temp eventually yielding a small pile of brown crystals. The product
obtained is suspected to be rather impure...  (Note: the pic below is not my
product from this extraction, pic will be posted later.)
Where do I go from here? I am having difficulty finding solubility data on 5-HTP so I don't know what solvent would be best for attempting a
recrystallization on the 5-HTP.
As for decarboxylation this is where I originally found the procedures for tryptophan -----> tryptamine (http://www.erowid.org/archive/rhodium/chemistry/tryptophan.h...) I plan on using either the carvone catalyzed or the ketone catalyzed
decarboxylation. Can anyone offer advice as to how I should go about this? If I attempt to use the tryptophan decarboxylation procedure for 5-HTP will
I have to change anything besides the stoichiometry? Can anyone offer info on 5-HTP solubility in different solvents? Is there any additional
information you'd like me to provide? Thanks to anyone that can provide help, as you will be rewarded with pretty pictures of serotonin if everything
works out. 
PS: The bottom attachment is the remains after attempting to evaporate some 5-HTP soln to dryness (not a good idea, no crystals and some probably
decomposed).
 
[Edited on 15-10-2012 by spotlightman1234]
[Edited on 15-10-2012 by spotlightman1234]
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SM2
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y not save the hassle and buy from one of the many vendors who sell you the pure actives, no ?' asked? The Natrol is superior for sleep...it has a
low tech extended release technology which relies on pariffin wax. Just like the Perduartes.
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Rich_Insane
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PureBulk sells large amounts of 5HTP powder for reasonable prices, iirc. See if your results are different with the pure material (or USP standard
"pure").
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spotlightman1234
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Quote: Originally posted by Rich_Insane  | PureBulk sells large amounts of 5HTP powder for reasonable prices, iirc. See if your results are different with the pure material (or USP standard
"pure").
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I'll be buying some pure 5-HTP I suppose, seems cheap enough. I'll compare the results I get between the two. As for my question about solubility and
crystallization I found a paper loaded with information about 5-HTP extraction, purification, crystallization and more!(http://dspace.knust.edu.gh:8080/jspui/bitstream/123456789/92...)
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spotlightman1234
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Here's a photo of the product I obtained from three capsules using the same procedure. This time allowing the solvent to evaporate to dryness at room
temp. The watch glass I let it evaporate on was covered with many small clusters of white/beige, needle like crystals each sticking out from a node.
Sorry for the low resolution picture.
Also on a side note, the 5-HTP/ethanol solutions I get from the extraction always have a brown, slightly hazy, appearance to them. Perhaps activated
carbon could help clean up the solution before I evaporate it? Anyway... I'll be tinkering.
[Edited on 19-10-2012 by spotlightman1234]
[Edited on 19-10-2012 by spotlightman1234]
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bbartlog
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If the extraction is performed at RT rather than at the temperature of boiling ethanol, is the resulting material still brown? I question the need for
the elevated temperature and think that it may be contributing to your brownish product.
The less you bet, the more you lose when you win.
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spotlightman1234
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| Quote: Originally posted by bbartlog | | If the extraction is performed at RT rather than at the temperature of boiling ethanol, is the resulting material still brown? I question the need for
the elevated temperature and think that it may be contributing to your brownish product. |
Ok, I repeated the extraction this time preforming it at room temp and allowed the ethanol to evaporate at room temp as well. This is what I got. As
you can see it is still brown, also I recovered less material than before (still have to weigh). I suppose the brown color may not be from
decomposition products, but idk.
Something promising however, is that when I washed the horrible product I recovered from the first extraction with a small amount of methanol some of
the brown gunk was removed and I was left with some fluffy, almost fibrous solid which is considerably cleaner. Although I'm not sure how much of it
is actually 5-HTP or what the impurities are.
PS: (Pictures going from top to bottom. First is the room temp product. Second is the same room temp product scraped together. The third is the first
extraction product washed with MeOH.)
 
[Edited on 27-10-2012 by spotlightman1234]
Attachment: phpxaGoxi (1015kB)
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sigma742
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Without better equipment you're going to have a really hard time separating those two without a large loss of your product.
Have you considered recrystallizing the sample?
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DDTea
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This is a very old thread but it is one of the first search results for "5-hydroxytryptophan extraction." So for anyone else who stumbles down this
disused path, here's a successful procedure for 5-HTP separation from a commercial product. It is, of course, unnecessary given that pure 5-HTP
powder is sold as a bulk nutritional supplement.
Starting material is capsules of 5-HTP (100 mg / tablet) with the following inactive ingredients: dicalcium phosphate, gelatin (capsules) and < 2%
of: silica, vegetable cellulose, vegetable magnesium stearate. Everything except silica has negligible solubility in water.
Ten capsules were opened and the contents poured into a beaker. 20 mL of boiling water was added and the mixture was agitated for about 2-5 minutes
with continued heating from a hot plate. The suspension was vacuum filtered, the filter cake washed with ~5 mL of boiling water, and the filtrate was
placed in a refrigerator ( 0 C or thereabouts). Crystals begin forming almost immediately. After 1 hour, the off-white/beige crystals were separated
by vacuum filtration. Yield: 417 mg (41.7 %) after drying. 1H-NMR (D2O) conformed to literature spectra.
5-HTP has a literature solubility of 2.5 g/100 mL in 50% boiling alcohol and 5.5 g/100 mL in boiling water ( https://pubchem.ncbi.nlm.nih.gov/compound/5-hydroxytryptopha... ) . An alternative way to do this extraction may be to dissolve the geltab
contents into boiling water and add ethanol, dropwise, until turbidity appears. Then grow crystals as usual. I have not done this or compared
yields--this boiling water extraction gets the job done even if yields are not spectacular (about on par for what can be expected in
recrystallization). A second crop of crystals could be grown as well, and I see no reason not to do just that: there should be an almost trivial
amount of impurities present.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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zed
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Well yes, you could do that. But, Melatonin is available directly to those of us in the U.S..
Might actually be cheaper than 5-HTP.
Not exactly Serotonin, but in the ball-park.
[Edited on 15-1-2019 by zed]
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Fantasma4500
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5 hydroxy... ugh you better store that stuff in a different cabinet than your methylating agents, just in case..
ive been wanting to turn L-tryptophan into tryptamine for a while, but the price of actual turpentine puts me off a slight bit, supposing that you
need real turpentine as the ""turpentine"" you can buy is completely different stuff
but if its soluble in water to some extent.. why would you need a solvent in the first place? L-tryptophan is a bit less soluble in water than 5-HTP,
so throwing the spearmint oil in solution maybe accompanied with a bit of acetone could maybe work out
speaking of acetone, maybe its just me being biased about acetone being a great solvent.. have you tried with acetone to remove the brown
discolouration? maybe you just need to learn to accept a multicultural yield.
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oblivionbubble
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Im wondering the same...
Will run 5-HTP in tetralin using cyclohexanone as catalyst.
I also have melatonin in pure form. How should i approach it?
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