Sciencemadness Discussion Board

Extraction of 5-HTP and decarboxylation to serotonin?

spotlightman1234 - 15-10-2012 at 11:49

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... :P (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 ( 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).

5-HTP bottle.png - 649kB Capsule powder.png - 992kB

[Edited on 15-10-2012 by spotlightman1234]

5-HTP burnt.png - 986kB

[Edited on 15-10-2012 by spotlightman1234]

SM2 - 15-10-2012 at 18:00

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 has a low tech extended release technology which relies on pariffin wax. Just like the Perduartes.

Rich_Insane - 16-10-2012 at 09:16

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").

spotlightman1234 - 18-10-2012 at 23:08

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").

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!(

spotlightman1234 - 19-10-2012 at 10:16

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.
5-HTP evaporated..png - 901kB
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]

bbartlog - 19-10-2012 at 17:32

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.

spotlightman1234 - 26-10-2012 at 21:12

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.)

Evapdish RT 5-HTP.png - 1.2MB RT 5-HTP scraped.png - 1MB

[Edited on 27-10-2012 by spotlightman1234]

Attachment: phpxaGoxi (1015kB)
This file has been downloaded 962 times

sigma742 - 3-11-2012 at 08:11

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?

DDTea - 10-1-2019 at 21:57

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 ( ) . 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.

zed - 14-1-2019 at 19:08

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]

Antiswat - 19-1-2019 at 02:40

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.

oblivionbubble - 22-9-2019 at 00:55

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?