Pink THH?

[arcologist]

So I've been working on reducing harmaline to THH via zinc + acetic acid, then precipitating out with NaOH. I tested the resulting white powder with marquis reagent and it seems to indeed be mostly THH (turns green).

However, I recently noticed that part of my vial of white powder has turned a very light shade of pink. I had done two separate procedures - one just basing out with NaOH, and the other performing a manske to try to precipitate THH (didn't work), then basing with NaOH. It was only the top layer of material (second procedure) that turned pink and I did the procedure less than a week ago. The vial has been kept in my refrigerator the whole time.

Does anyone have an idea of what could have happened here? I find the color change to be rather odd because the two layers of powder were initially the same color/consistency. The first layer had been sitting in the vial for 3 weeks or so with no color change. The only difference between the two batches was the failed manske step for the second one.

My ideas:
* Some contaminate from the second batch reacted with the THH. Possible contaminates: acetic acid, NaOH, NaCl, sodium carbonate, harmaline.
* The THH reacted with the air in the vial, oxidizing? (but why didn't the first batch?)

Unfortunately, the two layers of powder have since been mixed together so there's no way to test them separately. I might just try re-dissolving them and basing again to see what happens.

Update:
I tried re-dissolving and basing again with sodium carbonate. Interestingly, the powder immediately turned a significantly darker shade of pink as soon as it touched the water. I added vinegar to get it to dissolve and the resulting solution was kind of a pink lemonade color. I had to add quite a bit of base before it precipitated out of solution as a very pink solid (pictured), much pinker than before. I'm guessing that whatever conversion took place, dissolving the alkaloids accelerated the process. I tested it with marquis reagent and it was initially dark green (like THH) but then over 1 minute changed to an orange color. This didn't happen with the previously tested THH.

I should note that the white and pink powders both have a similar smell, kind of like vanilla.

 

[arcologist]

Well, I tried another zinc + vinegar reduction on the pink mystery alkaloids and it seemed to turn them back into white THH, so my deduction is that the pink stuff was some kind of oxidized THH (not harmaline or harmine as far as I can tell).

I'd be curious if anyone with more chemistry knowledge could elucidate what could have happened here. Hopefully they won't turn pink again!

 

[anonenium]

i know this may not help much but sue my eyes for seing this.

the filter that you were using, it was much more blue then it is normally suppose to be, maybe they use a more heavily bleached paper, but if you still have that paper around could you shine a uv lamp on it, the thing looks very bright to me, but not in the colours i have seen during my experiments. i just wanted to mention that.

what i find interesting is that what you got was white on prrcipitations, what i go was significantly more yellow then the base material.

if i was to guess there may be another metal inside the zinc that is reacting, i have had stuff turn random colours as well, i say dont worry about it, i had my thh turn a little bit pinkish after i put it in the fridge for a few days, i thought maybe it was reverting back to the stuff i had before in the jar next to it, but a few days later it went back to being a deeper yellow.

give it a week or two and tell me how it goes, and on a separate note have you tried the thh enhanced pharma yet? im still trying to work myself up to do it but it looks like you and me are the two ready to take the jump on this

safe landings.

 

[arcologist]

It's probably just the lighting/camera. In life the paper was white, it is a bleached filter though.

This isn't THH HCl, just freebase, maybe you had some harmine in there to cause the yellow color?. Weird that you also experienced the pink stuff, then it turned yellow. I'm going to ask one of my chemistry friends this weekend to see what he thinks could have happened. It's very possible that there are some impurities in the zinc I have, I got it from a pyrotechnics guy.

I'm planning on trying the THH pharma soon, maybe this weekend? I was a little off-put by the pink color but now it's ok again. I'm going to try to replicate the active ingredients of aya in the right proportions, take it all (+DMT) dissolved in OJ at once. Hopefully it'll work, because I've had only 1 successful pharma session and 6+ misfires, still getting the dosing right. Make me a little anxious about taking the plunge (the one success was quite arduous).

Safe travels if you do try it!

 

[merkin]

Yeah, old thread - I know...but!

The thing I love about nexus (esp to a non chemistry person) is that when something goes "wrong", someone always seems to have been there before you!

So I got this too. There is another thread I couldnt find which also had this pink thang happen. Maybe I will find later.

I have no idea about why's or whats so let me just report what happened.

Essentially:
--------------
Started 5g DHH HCl ex rue / vinegar / ammonia route (VDS)
Added 200ml vinegar 5%
Added 4g zinc
Added 1% HCl to drop pH to ~2

Stirred 9 hours.
Went from cloudy green coloured liquid to clear with zinc granules very visible
Left 6 hours settling still slight bubbling
Decant 2x and filtered through 3mm diatomaceous earth
dH2O wash zinc and filter
Solution at 280ml

Bright clear lumo yellow filtrate

On stirring, dropwise add 12% ammonia

Ph start @ < 3

Continue adding (white clouds on each drip almost immediately )
Clouds take longer to disperse as ph rises
Around 4.8+ starts losing clear transparency, clouding

Around ph6 losing nice Lumo yellow -- changed now to pinky brown tint and not as clear

At ph 7 quite cloudy liquid still clouds noticeably on drip
@ pH7.2 completely opaque now but still clouds on drip at surface

The thing is... its really PINK!!
The liquid is a darkish but clear pink/rosé color and the precipitate is lighter, giving a light pink appearance

Bluish uv glow on top surface edges sort of visible in daylight
Slight clearer layer forming at the top

White particulate precipitate visible if stirring slowed

8.7 liquid now getting darker less cloudy (clearer)

8.9 cloudy again, more particulate precipitation starting now

9.3 seems no more drip -> clouds.

Stopped stirring to let it settle before resuming the dripping
Still clouding increases

Resumed stirring

~9.5 ph change is now very slow. 8-10 drips per .01 ph

At 9.67 stopped stirring and adding. Removed magnet and ph meter to let it settle for filtering thru buchner vaccuum

Precipitate is very fine but PINK!!

Actually tested Marquis reagent - green!

Bioassay, as far as I can tell: THH My experience is limited but was pretty much not harmaline! Taste, neutral.

Started 5g DHH, yield 2.256g. Pretty pathetic, not sure what the heck happened here!

Tried more Ammonia 25% to up pH > 11. Nothing dropped out at all. Stayed darkish but clear rose-wine color.

*EDIT: found the other thread!

Found this comment and seems it may be relevant: (just to note I have done this zinc reduction about 4 times now and this was the only time this happened, usually its pretty much white THH)

I've done the zinc/acetic acid thh reduction a few more times since I encountered the purple/pink ''stuff'', and I have not gotten any pink at all. I've reduced the time of the zinc reaction drastically and I attribute this to the improvement.

When I got the purple/pink stuff I had done the reaction over the course of a few hours, then let it sit around for about a day before i filtered and based. But now I do the reaction with in minutes, filter quickly then base. Then redissolve the alks in acetic acid and let the excess zinc settle out. Then i filter again and add base......then filter and wash alks with water numerous times.

 

[Hyper Turtle]

Wow that color! Beautiful!

Sorry i can't really help, i've done the reduction only once so far and didn't get any pink.

The only major difference to what you did here is that i didn't use any HCl in the mix. My reaction time was several hours over night with stirring, settling time about 1h. I filtered through a coffee filter and based with 25% ammonia.

THH-enhanced pharma is gonna happen for me, one of these weekends

 

[downwardsfromzero]

What that colour immediately makes me think of is the harmala red pigment, especially when looking at the solution from which it precipitated. It looks as though there's a strongly-coloured byproduct from the reaction, and even a small amount adsorbed onto the surface of the precipitated THH gives it that frankly gorgeous pink coloration. The fact that the colour intensifies as the pH goes up is immediately suggestive of the similar colour change seen with phenolphthalein. I suspect there's some kind of dimerised or low-oligomerised reaction product that is responsible for this. Dimerisation is quite commonplace in organic dissolving metal reductions.

It's also possible that a coupling reaction has occurred involving some kind of impurity from the rue seeds but speculation is worth nothing compared to a careful analysis of the wine-red supernatant. (I hope you've kept it!)

 

[merkin]

(I hope you've kept it!)

Sadly, no I didn't. I don't have access to any form of proper testing facilities locally (nor honestly would I know what to ask for) and would assume I am very far from the majority of nexians who could. I guess at that point I was happy I'd got what I was shooting for - albeit pink it functions perfectly and is definitely (mostly) THH.