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Wondering if anyone has explored the chemical/physical properties of 5-meo DMT

Jan e Kharabat

Esteemed member
I acquired some 5-meo DMT a year ago and finally decided to play around with it a bit. It was an orange powder so naturally the first step was to purify. I dissolved it in naphtha, salted out with benzoic acid, dissolved the benzoate salt in water, added a good amount of NaOH (smaller amounts caused emulsions), and pulled with heptane. I ended up with pure glistening white crystals. They were really pretty, but... I wanted the rectangular plates... So I tried to heat it up and redissolve it. I noticed that some yellow oil separated and remained stuck to the sides and the solution turned a bit more yellow, even though it was colorless before. Once again... I didn't get any plates... So I redissolved, salted with benzoic acid, but this time even the benzoate was more yellow than before. I dried it up and did 2 quick acetone washes with very small amounts of acetone, no more than 20ml in total. The acetone had light orange color, the precipitate became more clear.

I redissolved in water, based again with NaOH, pulled with heptane. I left it on the table, but ended up moving around a few things and the jolts and vibrations caused the crystals to crash out much sooner and they were even smaller than before, and again no rectangular plates... So I heated up the heptane, thinking it might have been some other stuff which is heat sensitive as 5-meo DMT ought to be quite stable, or at least so I thought. Same thing once again, solution turned more yellow, and the pretty white crystals I had just dissolved came out more orange a few hours later...

I thought of doing another test. After freeze precipitation, I took the left over heptane and added FASA to it. I ended up with some fumarate, which I didn't weigh but was definitely at least around a 100mg by the looks of it. It was light orange colored. I redissolved it in a small amount of IPA and the solution turned very dark orange. I left it standing, nothing crashed out, put it in the freezer, nothing crashed out, evaporated the IPA and ended up with some red looking stuff which was more oily than before. Now just to make one last test, I added some CaOH, moistened it a bit, left it to dry out, then pulled with acetone, and salted with citric acid dissolved in acetone. A miniscule amount crashed out, barely 4-5mg.

Now I have more questions then I started off with... Where did all that fumarate go? Is it just oligomerization or is there something else going on? If it's oligomerization, why does the orange oil suddenly become insoluble in heptane? How come the salt changes color after precipitation, and that too at a temperature of no more than 80 degrees C (that is the the temperature of the heating plate, the container itself with the solution in it probably doesn't get as hot). After the initial purification step, I had ended up with around 800mg of pure white crystals, in the end it was 600mg of light orange crystals... Where did the rest go? I am very very meticulous with everything and suck up every last bit of heptane during the A/B and I make sure nothing is spilled, nothing goes to waste... With DMT, I barely lose 20mg in an A/B cycle, so I cannot figure out where did those 200mg go, and specially that fumarate. Does anyone know better? Does 5-meo break down or change/oxidize more readily than the normal DMT?
 
Not exactly what you want to know, but just as a bad news:

While in theory you would never loose anything and just increase purity by doing Rex and A/B cycles, in my eyes doing too much can also make things worse x_x

For example take 1 g of completely white DMT and still do a Rex. I bet while it melts on the hot glas while being in Naphtha you will create some red stuff that will not make it into the laterly formed new white crystals.

So any process of heat might "destroy" some alkaloids, no idea what happens but at least it s not accessible for your final and desired hopefully pure product.

Especially if you were after a certain crystal geometry: as crystal formation seems to be still quite a mystery and influenced by so many factors, maybe it would anyways be not realistic to exactly get to crystal shape XY :(((
 
Does 5-meo break down or change/oxidize more readily than the normal DMT?

I believe that 5-meo-DMT-N-Oxide has a pale brown color, which can appear orange in concentration and yellow in dilution.
I think oxidation is a likely explanation for what is happening.

It seems like some weight is always lost when recrystallizing something and that when working with smaller amounts of things that the fraction which is lost is greater in proportion to the total amount.

As for the missing portion, did you evaporate and weigh the residues from the acetone wash?
 
Sounds to me very much like the stuff's sensitive to oxygen and/or light and these manipulations should be carried out using the appropriate precautions like inert atmosphere and dim red light.

@Dasein - what type of lighting were you using? This may be an instance where old incandescent bulbs would be desirable, even.
 
So it sounds like DMT is more resistant to oxidation than 5-meo. Perhaps the chemistry experts could explain why that would be so... What's surprising is the loss in salt form... I assumed that the salt would be much more stable. I will evap the acetone and see what comes out. Usually I don't have much difficulty with creating specific kind of crystals, you need the right container, the right amount of concentration etc. But I'm a bit out of practice I guess. Oh well, I guess I'll stop wasting the precious stuff for now.
 
The methoxy group changes the electronic properties of the ring system and this in turn will affect things like solvent interactions and sensitivity to air and light.

Did you have a think about your lighting?

I wonder if there are any lab notes anywhere on 5-MeO recrystallisation? These sorts of things should be covered somewhere in the literature, although light sensitivity isn't mentioned in TIHKaL (but Shulgin did re-x the freebase from hexane and the hydrochloride from EtOH/Et₂O).
 
I recovered a small amount, 10-20mg from the left over acetone solution, which either means that the citrate salt is not completely insoluble in acetone, or that my acetone is not as dry as I thought. I also used acetone to dissolve the freebase the second time because I didn't want to use heat or large amounts of solvent, I salted out with benzoic acid dissolved in naphtha. But if my acetone is not really dry, there might be some amount left in the solution after salting out. If that is the case, that will make up for most of the lost amount. Still... It seems to be rather sensitive to heat.
As for the light, I have been working in the day light but it's cloudy all the time and pretty dark. I have one normal incandescent bulb, probably 50 watt or less. Still... The fumarate salt going orange is a bit strange.
 
On a side note, the benzoate salt vaporizes pretty well. I tried 210 degrees Celsius (with divine crossing v5), but a bit higher might probably be more effective. I have to start inhaling at around 160 degrees mark, otherwise it starts to give off that sweet benzoic acid smell and the vapor becomes harsher. As one still only needs around 10-12mg of salt, the volume is still pretty small and easy to inhale all one needs in one toke. I didn't have any of the difficulties I had with DMT benzoate, the 5-meo benzoate vaporized better, didn't solidify too quick, didn't clog the inside of the vaporizer dome like the DMT benzoate.
So, I think benzoate salt is the best way to go for 5-meo, it's more stable, easier to dose, owing to the increased weight, easy to vaporize, can be snorted or used sublingually. I tried both the other methods, and while the sublingual and snorted experiences were both very different, the 5-meo was very much active on its own. There's no need for freebase!
 
Another update, it seems like the salting process also induces a color change. I converted all the freebase (very light tan colored) to benzoate. I added a concentrated solution of benzoic acid dissolved in hot naphtha (75-80°). I added it all in one go instead of drop wise. A yellow waxy layer settled at the bottom within 10-15 min after adding benzoic acid, but the solution was still cloudy, so I left it standing and over the course of next few hours, tiny crystals started to grow on the sides of the container. I left the solution in the fridge over night, poured off the naphtha, and now I have a bowl with a yellow waxy layer at the bottom and pink/orange colored crystals on its walls. So, the benzoate which crashed out right away is lighter colored than the crystals which took longer to grow. I also noticed that upon vaporizing the orange crystals, a dark oily residue is left behind which doesn't evaporate, at least not at 230°, which seems like the optimum temperature for 5-meo benzoate. So... One conclusion to be drawn from all of this is that 5-meo is quite sensitive to oxidation, probably a bit more than DMT. And some sort of change occurs during the salting process and the salts can also change... At least their color, after crystallization. Heat, even at 60-70° can induce the color change, which may suggest that the salts are also prone to oxidation or some other chemical/morphological change. I hope someone else can further investigate this.
 
Also, after playing around with 5-meo for a week, I'm gonna stop now... I had to test it multiple times, see if the left over oil is active, if the soapy layer between polar and non polar layers has any actives in it, the right temp for vaporization, intranasal and sublingual routes etc etc and... It weighs a bit on the heart I think. And I keep having dreams where I somehow die and then the 5-meo trip kicks in... I have had multiple trips in my sleep, my heartbeat feels stronger than usual, goes up too fast and takes longer to come back to normal. I also noticed that my hands were shivering for a few days afterwards. So, I'm not gonna touch it for at least a few months.
 
Also, after playing around with 5-meo for a week, I'm gonna stop now... I had to test it multiple times, see if the left over oil is active, if the soapy layer between polar and non polar layers has any actives in it, the right temp for vaporization, intranasal and sublingual routes etc etc and... It weighs a bit on the heart I think. And I keep having dreams where I somehow die and then the 5-meo trip kicks in... I have had multiple trips in my sleep, my heartbeat feels stronger than usual, goes up too fast and takes longer to come back to normal. I also noticed that my hands were shivering for a few days afterwards. So, I'm not gonna touch it for at least a few months.
You're saying you've been using the 5-meo for a week and now you're having the side effects you described? If so, that'd be what's commonly called reactivations. 5-meo is different from most other psychedelics in the way it can produce effects like those for a week or two after the trip. It's especially more likely to happen if you trip a bunch of times in quick succession. It should calm down within a couple weeks or less, and you'll feel perfectly normal. If/when you start again, it'd be better to space your individual trips out by at least a week in my opinion.
 
Hi,

You will never get rectangular crystals from crystallisation from solvent. They are produced by vacuum distillation only.

It it less prone to oxidation than DMT. And it won't form the n-oxide readily. I kept 5-MeO at 80C for over 2 weeks before with very minor degradation.
 
Hi,

You will never get rectangular crystals from crystallisation from solvent. They are produced by vacuum distillation only.

It it less prone to oxidation than DMT. And it won't form the n-oxide readily. I kept 5-MeO at 80C for over 2 weeks before with very minor degradation.
Do you know if a salt form like 5-MeO-DMT fumarate would be similarly stable in solution with water? Assuming it's stored in good conditions (dark, dry, airtight, etc.)
 
I did get the rectangular plates via recrystallization once... I think with the right concentration and other conditions, it is possible. Also, something is definitely happening there and it's more than a simple change in color. The crystals were pure white, they grew more yellow upon salting with benzoic acid once, I converted back to freebase with sodium hydroxide, pulled and salted again with benzoic acid, and this time, the color went orange. I washed the benzoate crystals with acetone and the color became significantly lighter. I evaped the acetone and ended up with an oil that would not solidify. I vaporized that oil, and there was a small amount of 5meo in there but not a lot. Considering the amount of oil, if it was all 5meo, it would have been much more potent. After a 20ish second inhale, I checked and the oil had grown darker and a good fraction of it wouldn't vaporize. Also, there was another taste and smell in there, different from the more pure benzoate I had vaporized earlier.
 
Well, initially as a purification step. It was an orange powder when I got it, the first salting step worked well, then I wanted to play around and... ended up with an entire series of salting steps and acetone washes etc. What was bothering me was the color change from pure white to yellow/orange. I wanted to see what is going on there, and for whatever reason, some of it did change to an inactive oil. Also, benzoate can be snorted and used sublingually.
 
Well, initially as a purification step. It was an orange powder when I got it, the first salting step worked well, then I wanted to play around and... ended up with an entire series of salting steps and acetone washes etc. What was bothering me was the color change from pure white to yellow/orange. I wanted to see what is going on there, and for whatever reason, some of it did change to an inactive oil. Also, benzoate can be snorted and used sublingually.
Try when you put heptane in the freezer, to check on it 20 minutes later, if orange oil came out, transfer all heptane to another dish. This should give you white crystals. 5-MeO loves to oil out as orange oil.
 
Yes but that's the weird part... The coloration comes during the salting step, and whatever it is, it's fairly soluble in acetone, which 5-meo benzoate isn't. Same goes for fumarate, the freebase crystals were pure white, upon salting with fumaric acid, the fumarate crystals became light orange. The acetone wash cleared up the color, evaporating that acetone lead to an orange oily powder/paste, which contained some fumarate, as the acetone was not completely dry (although in the case of benzoate, only very minute amounts got carried away with acetone wash), but still... It begs the question, what exactly is responsible for the change in color during the salting step, and why is it more soluble in acetone.
 
I had orange powder/crystals form from the mother solution during salting. Tested at only like 20% 5-MeO 80% fumaric acid if I remember right.

I'm very surprised you salted it out as an orange powder, unless not washed correctly and the solution stains the powder. It should be white to off white.

I dissolve 5-MeO-DMT in hot acetone then add fumaric acid till ph4-5 then filter and acetone wash.
 
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