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Harmine, harmaline and THH from Syrian Rue. Verification and finetuning of the VDS-protocols
- Thread starter An1cca
- Start date
exquisitus
Rising Star
pure awesomeness jees, thanx for posting.
now if only anybody compiles an (easy to follow) tech for us chemistry-challenged folk...
now if only anybody compiles an (easy to follow) tech for us chemistry-challenged folk...
An1cca
Rising Star
Nice work Jees, as usual :lol: ... I use the same Norit capsules as you do, so they contain iron and titanium oxides. No big deal I think and at least I did not experience any transformations when cleaning up with it.
Filtering off AC can be challenging with regular coffee filters. I use round filters that were ordered online and filter particles up to 5-8µ. One pass is enough to take out all of the AC. I think what you were looking for is Celite, but I don't use it myself since filtering works well enough.
Crystals tend to take some time to rearrange themselves from tiny particles to 'big' structures. When recrystallized in situ, I usually wait for about ten miutes before inspection, although observing how they form is fascinating as well
Any pictures of recystallized spears?
As for a tech, Exquisitus, you would already do well by following the methods described in VDS's paper (chapter 2). They are detailed enough and were sufficiently checked in the 11 preceding pages of this thread :d . We're awaiting the LC/MS results to (hopefully) open the champagne-bottles and then I'll edit the opening post to provide step-by-step procedures based on the paper and the extra tips&tricks from this thread.
Good luck!
Filtering off AC can be challenging with regular coffee filters. I use round filters that were ordered online and filter particles up to 5-8µ. One pass is enough to take out all of the AC. I think what you were looking for is Celite, but I don't use it myself since filtering works well enough.
Crystals tend to take some time to rearrange themselves from tiny particles to 'big' structures. When recrystallized in situ, I usually wait for about ten miutes before inspection, although observing how they form is fascinating as well
Any pictures of recystallized spears?As for a tech, Exquisitus, you would already do well by following the methods described in VDS's paper (chapter 2). They are detailed enough and were sufficiently checked in the 11 preceding pages of this thread :d . We're awaiting the LC/MS results to (hopefully) open the champagne-bottles and then I'll edit the opening post to provide step-by-step procedures based on the paper and the extra tips&tricks from this thread.
Good luck!
An1cca I think you are right about in situ needing time, that was my initial main problem as the concentration was too high and it went crazy. And right also about in-situ being the best bets on ID'ing a component.
My camera hand held shots were difficult, so I tinkered an adapter between microscope and camera (pic 1 and 2), the camera can slide forward-aft for best results. No more hand shaking. The nylon bolts are to fine tune end positioning. I can have long shutter times now ( + time delay shutter activation), and with low ISO setting for best quality. After touch with Adobe Lightroom.
So here are the views on in situ of "a strange visitor".
A penny for your thoughts...
First one 100x , the two last ones 400x
My camera hand held shots were difficult, so I tinkered an adapter between microscope and camera (pic 1 and 2), the camera can slide forward-aft for best results. No more hand shaking. The nylon bolts are to fine tune end positioning. I can have long shutter times now ( + time delay shutter activation), and with low ISO setting for best quality. After touch with Adobe Lightroom.
So here are the views on in situ of "a strange visitor".
A penny for your thoughts...
First one 100x , the two last ones 400x
Attachments
An1cca
Rising Star
Impressive setup and results! Well, the pictures make me think of THH in the first place. What I forgot to say was also that I stopped using a cover-slide on my recrystallizations. This keeps the 3D-aspect of the crystals untouched. This is how I obtained the harmine 'needle-balls' of post #160. Before, harmine only presented itself as loose needles because I 'crushed' the balls with my cover slide.
You're obtaining some nice material for deep-dreaming Jees! AI Image Generator :shock:
You're obtaining some nice material for deep-dreaming Jees! AI Image Generator :shock:
Not pure THH for sure, looks too different, and The Unexpected Visitor (TUV) precipitated before DHH did, while THH would crash out after DHH (higher pH). FWIW.
In 1st pic: TUV in vessel crystallized;
2nd pic THH (vessel) in same scale.
Last pic THH (in situ) same scale (bolders are smaller)
I've checked your post #135 at page 7: all the in between stages from DHH to THH, most of them do not fit, just one, see next post.
TUV was created out of a manske that contained a lot of salt contamination, so I will re dissolve & re pricipitate TUV in a clear water and see where it's pH depression lies truly without all that salt. And to see if other crystal-form shows up.
Then I'll try reducing it, if it really stems from DHH it will reduce further.
...
In 1st pic: TUV in vessel crystallized;
2nd pic THH (vessel) in same scale.
Last pic THH (in situ) same scale (bolders are smaller)
I've checked your post #135 at page 7: all the in between stages from DHH to THH, most of them do not fit, just one, see next post.
TUV was created out of a manske that contained a lot of salt contamination, so I will re dissolve & re pricipitate TUV in a clear water and see where it's pH depression lies truly without all that salt. And to see if other crystal-form shows up.
Then I'll try reducing it, if it really stems from DHH it will reduce further.
...
Attachments
An1cca
Rising Star
Or could it be harmine with just a little DHH contamination? As we've seen, mixtures of alkaloids can take very different crystal shapes (e.g. har-dhh caterpillar). Or indeed the presence of NaCl? It would be so unexpected to retrieve another alkaloid in between harmine and DHH... :?
Another way to identification might be to do a microscale hydrogenation of some crystals to check if it turns to THH. 2 drops of vinegar on a slide, dissolve some TUP-crystals, add a pinch of Zn-powder, let react for 30 min, scrape Z'n aside and add 1 drop of ammonia 12%, wait and observe... Will perhaps give some more information?
Another way to identification might be to do a microscale hydrogenation of some crystals to check if it turns to THH. 2 drops of vinegar on a slide, dissolve some TUP-crystals, add a pinch of Zn-powder, let react for 30 min, scrape Z'n aside and add 1 drop of ammonia 12%, wait and observe... Will perhaps give some more information?
"The unexpected visitor" TUV (or TUFriend or TUProduct) dissolved in a dash vinegar + water to 100ml, based with ammonia, pH depression set in at 7.85 and rolled back to 7.00 . Up to pH 8.00 and filtered + dried.
None of the previous forms remain which indicate TUV is not a 'pure' component but an altered form of a pure component(s), a bastard LOL.
After the pH depression clearly ended, the filtrate of pH 8.00 got more based with ammonia to pH 10. Very slowly some very slightly yellow tint vanished to make a white glittering precipitate. This was harmaline as showed by vessel crystals and in particular by the in-situ fern crystals. No pics of that, please believe: just regular harmaline, not much really just some tiny dust layer.
So TUV was a mix form of harmaline + [?]
This [?] seems to lean much toward Harmine, see pics.
Pic 1: the [?] in vessel crystals, being TUV minus some DHH content.
Pic 2 and 3: the [?] insitu crystals.
This really intrigues me: when does a mix of components behave like a "new" component with an own pH depression and an own crystal signature in vessel and insitu? Like TUV.
(An1cca what especially triggered your caterpillar mix form to succeed?)
Or: when does a mix of pure components split up nicely according to the pH depressions of the 2 pure components, and the crystals (in vessel and insitu) are recognizable as separate different distinct crystal forms?
Could the heavy salt contamination (coming of a former manske) forged the TUV?
Because I now re-dissolved TUV, hence the salt contamination lessens, and lo and behold TUV is already falling apart, so there are indications that "impurities" might forge crystals to merge and make life for us more difficult for ID'ing, but who knows also in relation to THH reduction-abilities/yields?
So the mantra goes again: only work with very cleaned up products (even salt does 'things' ). I'm not done with the remaining [?] altered TUV yet, will do some extra A/B'ing.
None of the previous forms remain which indicate TUV is not a 'pure' component but an altered form of a pure component(s), a bastard LOL.
After the pH depression clearly ended, the filtrate of pH 8.00 got more based with ammonia to pH 10. Very slowly some very slightly yellow tint vanished to make a white glittering precipitate. This was harmaline as showed by vessel crystals and in particular by the in-situ fern crystals. No pics of that, please believe: just regular harmaline, not much really just some tiny dust layer.
So TUV was a mix form of harmaline + [?]
This [?] seems to lean much toward Harmine, see pics.
Pic 1: the [?] in vessel crystals, being TUV minus some DHH content.
Pic 2 and 3: the [?] insitu crystals.
This really intrigues me: when does a mix of components behave like a "new" component with an own pH depression and an own crystal signature in vessel and insitu? Like TUV.
(An1cca what especially triggered your caterpillar mix form to succeed?)
Or: when does a mix of pure components split up nicely according to the pH depressions of the 2 pure components, and the crystals (in vessel and insitu) are recognizable as separate different distinct crystal forms?
Could the heavy salt contamination (coming of a former manske) forged the TUV?
Because I now re-dissolved TUV, hence the salt contamination lessens, and lo and behold TUV is already falling apart, so there are indications that "impurities" might forge crystals to merge and make life for us more difficult for ID'ing, but who knows also in relation to THH reduction-abilities/yields?
So the mantra goes again: only work with very cleaned up products (even salt does 'things' ). I'm not done with the remaining [?] altered TUV yet, will do some extra A/B'ing.
Attachments
An1cca
Rising Star
Ok Jees, this research will surely be integrated in the VDS-Nexus protocol to come. I also think that one 'has to respect the chemistry'. Harmala alkaloid extraction may be safe and simple, but one cannot cut corners it seems.
TUV sure looks like harmine, although the pH's point more towards DHH (indicating once more that fixed pH-numbers can not serve as a golden standard). The caterpillar from post #147 (and its psychedelic cousin from post #161:d ) came about by recrystallizing a 50/50 mixture of har/dhh without cover slide. I'm sure you could make a nice foto-shoot of that mixture with your setup. It's a pleasure to watch the crystals grow as well! Do you have a video-option on your camera? I could never hold my phone still enough to make a decent video of crystal formation. Would make a nice projection for V-jays I'm sure...8)
TUV sure looks like harmine, although the pH's point more towards DHH (indicating once more that fixed pH-numbers can not serve as a golden standard). The caterpillar from post #147 (and its psychedelic cousin from post #161:d ) came about by recrystallizing a 50/50 mixture of har/dhh without cover slide. I'm sure you could make a nice foto-shoot of that mixture with your setup. It's a pleasure to watch the crystals grow as well! Do you have a video-option on your camera? I could never hold my phone still enough to make a decent video of crystal formation. Would make a nice projection for V-jays I'm sure...8)
ijahdan
Rising Star
Update: I finished doing the five separation stages, using bicarb for harmine and carb for harmaline. Seemed to work as expected, with the final precipitation with sodium carbonate pulling only a tiny amount of harmaline.
The final precipitates had a lot of carb/bicarb contamination, especially the harmaline, which had crystals of sodium carbonate forming when dried. I redissolved in vinegar and reprecipitated with ammonia. This seems to have done the trick and also produced much whiter harmine/harmaline. Might be worth using ammonia instead of sodicarb for the harmaline stages in the separations...
Ive now got the harmaline reducing with zinc. Will precipitate the (hopefully) THH using an excess of ammonia, which should leave any zinc hydroxides in solution.
Bioassayed the separated harmine (100mg sublingually) last night and it feels very clean. No harmaline hangover this morning. Wish I had more accurate means of testing though.
The final precipitates had a lot of carb/bicarb contamination, especially the harmaline, which had crystals of sodium carbonate forming when dried. I redissolved in vinegar and reprecipitated with ammonia. This seems to have done the trick and also produced much whiter harmine/harmaline. Might be worth using ammonia instead of sodicarb for the harmaline stages in the separations...
Ive now got the harmaline reducing with zinc. Will precipitate the (hopefully) THH using an excess of ammonia, which should leave any zinc hydroxides in solution.
Bioassayed the separated harmine (100mg sublingually) last night and it feels very clean. No harmaline hangover this morning. Wish I had more accurate means of testing though.
An1cca
Rising Star
ijahdan said:
Article confirmed again. Can be considered 'Nexus-approved' imo. Thanks Ijahdan!:thumb_up:
ijahdan said:
Yes, gives you clean DHH without going through reprecipitation-steps. Sodium carbonate is only used to provide an ammonia-free route. Personally, I still wash all my precipitates with ammonia 3-6% (e.g. 3x 20ml).
ijahdan said:
Correct, should work out this way. Let us know so we can make this procedure Nexus-approved as well. LC/MS-results will hopefully be the cherry on the cake...
ijahdan
Rising Star
Thought Id try reducing some mixed alks while I wait for the harmaline to settle after reprecipitation. Dissolved in vinegar, added zinc, left for 24 hours, filtered. When I started adding ammonia, at first, white clouds formed and disappeared. I added more ammonia, stirring continuously until the precipitate stayed. Then a strange thing happened. The brown goo started to form and stick to the sides of my container and the stirring spoon.
Managed to scrape it off and get it all floating again. Added some more ammonia for luck and left to settle overnight. Ill try to attach a picture. Looks like big brown crystally goo. The alks I started with were an off white fine powder.
I had similar looking gooey crystals forming in alks which were dissolved in vinegar and left in a cold place for a few days. This happened without any addition of base.
Could it be something to do with the low temperatures in my secret lab? Close to zero at night. Anyway, Ill redissolve, reprecipitate at room temperature and try adding the ammonia more slowly this time.
Will definitely try and get hold of a microscope.
Managed to scrape it off and get it all floating again. Added some more ammonia for luck and left to settle overnight. Ill try to attach a picture. Looks like big brown crystally goo. The alks I started with were an off white fine powder.
I had similar looking gooey crystals forming in alks which were dissolved in vinegar and left in a cold place for a few days. This happened without any addition of base.
Could it be something to do with the low temperatures in my secret lab? Close to zero at night. Anyway, Ill redissolve, reprecipitate at room temperature and try adding the ammonia more slowly this time.
Will definitely try and get hold of a microscope.
