Why is it yellow?

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I've been searching for answers and sprinkled questions among different threads, gathering some theories. But I still haven't figured it out so I'm just going to start compiling my research here.

To summarize, I'm getting little prisms with nice morphology, but the color is yellow. Ever since the first pull on the bark the solvents have been yellow whenever the spice is dissolved. I really thought I escaped the color when converting to DMT-benzoate, because that salt was very white. But a water re-x of the benzoate powder still grew salt crystals with a yellow tint. And after converting back to freebase, the crystals grown are nicer and more transparent than ever, but still yellow.

View attachment VID_0071.mp4
Included is a video example of one of the crystals. I was originally inspecting the geometry, but I also noticed that the color changes between yellow and colorless depending on what angle you're looking at the crystal. I posted this in a gemology community to ask them if this is pleochroism, and they seemed confident it was not. But it seems to fit the definition to me and no one explained their reasoning for why not.

Yet I have seen photos of DMT "diamonds" that seem unanimously colorless. So even if mine are pleochroic, that doesn't help me understand why mine are that way and others are completely colorless.

Ultimately, I'm trying to find a way to decolor it. Any suggestions?

Below is the process these have gone through so far.

I extracted at 60 celsius from MHRB, and got a yellow dusty waxy crude. Everything following was done at room temp.

I washed the solids with aqueous sodium carbonate solution a few times because I forgot to wash the naphtha pulls.

Then I dissolved the water-washed crude in a solution of HCl. I washed the aqueous dmt.hcl solution with naphtha a few times.

Freebased it again with NaOH solution and clouds of white precipitate settled into an orange oil above the salt water.

I pulled from the dmt oil / salt-water with hexane, and salted the DMT out of hexane with benzoic acid-saturated hexane, instantly crashing out insoluble DMT-benzoate. The hexane went back to pull more of the oil, where excess benzoic acid gets neutralized by excess NaOH.

After everything was pulled and converted to benzoate I vacuum filtered the solvent out the benzoate powder, and washed it with fresh hexane and naphtha a few times to pull off any stray freebase or benzoic acid residue.

Then I dissolved the benzoate salt in distilled water, and washed it with clean hexane and naphtha a few more times before freebasing it with NaOH again. I used hexane again to pull the freebase oil layer.

The combined hexane pulls were washed with dry ice, attempting to convert any NMT in solution to NMT-carbamate, which should have precipitated as a goo. No precipitation was observed, so I did not follow through decanting into another vessel. The solution sat for a day without precipitation. Then it was washed with aqueous NaOH solution once, clouding the hexane with presumably micro water drops. This sat for another day, and still had a minor haze.

The final solution flowed through 0.22 micron PTFE syringe filters, to block any micro water content, particles, spores, bacteria. The filtered hexane was crystal clear. In the crystal vessel, I hadn't even finished filtering the solvent before I could see sparkles smaller than dust forming.

Within 24 hours of just sitting there at room temp most of the growth had occurred, leaving 2mm sq flawless crystals. I got greedy and tried to slowly cool then freeze to grow them larger, and I think a few did grow, but most just got ruined by tiny growth nucleating off the gems.

Polymers?
I've targeted polymers during the acid phases of a couple mini A/B's. Both the saturated HCl and benzoic acid solutions were yellow though, and in the end hasn't removed any color. Non-polar solvent washes on the aqueous dmt salt solutions would turn the same yellow color. If allowed to rest for a day, the yellow color would fade, presumably back into the aqueous layer. I tried to separate the yellow with solvent washes but ran out of solvent before I could wash it out completely. It's inconclusive whether the solvent was pulling a yellow impurity or DMT itself.

NMT?
I targeted any potential NMT with a dry ice CO2 wash. I didn't see any goo precipitate though, nor did it affect the color of the solution. I may revisit this.

DMT-NO?
Apparently this is debunked, but N-Oxides are technically a potential culprit. I plan to try a zinc reduction just to see, but N-Oxide is supposedly water soluble, so it should have been well removed by now during the numerous washes and filtrations.

Polymorphs?
I did a melting point test and got 66-69 C. None of the other diamond growers have reported melting points; but in literature, other researchers reporting this melting point have reported colorless prisms. This seems to contradict some suggestions that there's a lower melting, colorless polymorph that slowly changes to the yellow, higher melting polymorph during storage or heating. Considering other people have gotten the higher melting polymorph without the color change. And I've seen pictures of yellow crystals that were not prismatic, but again no associated melting points reported. I'm not ruling out polymorphism but idk if there's enough data to conclude one way or another.

 

[GnomesAndElvesInHarmony]

It's all good, some of the posts were over ten years ago.



Notably, none of your posts about zinc advised using it; no mentions of using it to resolve autoxidation.

When I started researching the yellow color a year and a half ago, you weren't around! So I spent months and months reading all the relevant threads I could dig up, each and every one. There is so much conflicting info on zinc that I never felt confident enough to try it until this week after reading about IridiumAndLace's results in the minimum polymer thread.

Anyway, I think you're the only source on the nexus for autoxidation. So I'm extremely grateful that you're here now and actively responding to questions I've had for many months. It's like that saying "when the student is ready, the teacher appears".


That's good to know for minimizing autoxidation. But if it can be reversed with a two second zinc wash, I'm not sure if it's worth the time to store it as a salt vs freebase. Does allowing DMT to autoxidize enable or accelerate further degradation, thus warranting minimal autoxidation?

While refining my yellow DMT, I precipitated it out of hexane with benzoic acid. The DMT-benzoate powder looked extremely white, and was so fine, like a pharmaceutical powder. Then when I dissolved it in distilled water to recrystallize, the solution turned yellow. The DMT-benzoate crystals that grew back were yellow.
View attachment 111895
I believe benzoic acid is an antioxidative acid, so it really stumped me how a white powder could turn yellow. It's part of what drove me crazy on this quest, after concluding that the white benzoate didn't turn back yellow, the yellow just never left and the powder was likely too fine to see the true color.

So for resisting autoxidation we have:

• Salt forms, specifically organic acids.
• Polymorphs with favorable side chain rotations.
• Inert atmospheres.

Basically the idea is to molecularly shield the 2-position from oxygen molecules? Is autoxidation impossible in an inert atmosphere? Even if you left it in direct sunlight as freebase?

And for autoxidation remedies we have:

• Zinc + acid bath.

Here the science is H+ ions rip electrons from the zinc and donate them to the deficient DMT molecules.
Are there other ways?


You said autoxidation can be reversed by recrystallizing, but I guess I don't understand how that works?

Interesting. Any difference in how it has affected the 'experience'. (if any)?

 

[benzyme]

Basically the idea is to molecularly shield the 2-position from oxygen molecules

exactly.

Is autoxidation impossible in an inert atmosphere?

not impossible, but improbable

Even if you left it in direct sunlight as freebase?

UV light is energetic. It can cause double-bond shifts (then again, so does a microwave), even if a compound is under inert gas. This is theoretical, I suppose; only an experiment could result in true knowledge.

You definitely seem to get what's going on. This isn't exclusive to dmt, the discoloration occurs with other simple tryptamines as well; DET, DPT, NMT, and tryptamine itself, as well as indole. It isn't necessarily degradation, but an inherent property of those molecules, because of that reactive 2-position. Recrystallization reorients the crystal lattice, and thus redistributes electron localization.

And you mentioned the same word I use, "shielding". Some tryptamines like 5-MeO-DMT seem to be more resistant to discoloration; it has to do with electron localization, as well as the position of the terminal amine. Consider this diagram of DMT; it shows the terminal amine pointed straight out. That is the most commonly depicted form of DMT. Now imagine the alpha carbon rotated so that amine is pointed downward. Now the amine and its methyls are closer to that 2-position.
Keep in mind, that's just a linear representation. The rotation is, of course, in 3 dimensions. Electrostatic maps in molecular visualization programs help to better conceptualize it.

I've learned alot in ten years, mostly that there's alot that I don't know. What holds greater weight over theory is data, and repeated experiments showing the same results. What I do know is how to run LCMS, and I bought mine 10 years ago. I've mainly run dmt samples on it, from phalaris and hostilis extracts, to several synthetics. Probably over a hundred runs. I've only seen N-oxide once or twice, and never NMT (from others' samples). Most were all DMT.

 

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Interesting. Any difference in how it has affected the 'experience'. (if any)?

I've only tried the yellow crystals once, a full 50mg vaped in the volcano. It was a very strong trip, possibly beyond anything I've experienced before. But it had been years, so maybe I had just forgotten how insane it can get. A good metaphor is a consciousness-hosting digital universe. Apparently some AI / Tech people are trying to actually build this and upload their consciousness. The beyond portion was in this place free from time/distance. And climaxed with the realization that my soul was ethereally merged with the person I love in there, we were so close we were one. My whole body was vibrating, I was quivering. It was like an orgasm that lasted for minutes. Never felt anything like it.

Most DMT from internet extraction teks is over 90% pure, sometimes over 95% pure without additional steps. My refined yellow crystals are very translucent and 3-D, indicating high purity, likely 99%+. And even that is just one of DMT's growing "habits". I've dissolved the gems in solvent and regrown gems, then transferred the solution to the freezer and crashed out the traditional snowflakes from the same solution. Basically, snowflake habit can be just as pure as gem habit. Removing the color, even if it was from N-O, would likely only improve the purity by tenths of a percent. And as Benzyme is explaining, pure DMT can become and be yellow while still pure. Restoring electrons to yellow DMT and making it colorless is purely for aesthetics I think.

So my strong experience could be due to the DMT being very pure, but I doubt I could tell the difference between a 90% pure DMT and a 93% pure DMT -- so idk why there would be a noticeable difference between 97% and 99.9% I doubt the color affects anything past 99%.