Harmine Crystals from Syrian Rue

[soulfood]

You shouldn't use IPA or any other alcohol unless its done without any oxygen present. It causes a red color to form from degradation of the alkaloids. The longer they sit in it, the redder it gets, and the more your alkaloids are converted to harmala red. This is why alcohol is not normally used to extract harmala alkaloids. Its great for making harmala red though, which is why your IPA solution is red.

Acetone seems to also do this.

Ok after that little mishap SWIM has dried the lot and he's looking at a mixture of white, palish brown and a little bit of red. It's all pretty mixed up, but does anyone know of a tried and tested method to get the good stuff out?

SWIM's a little frustrated with himself for rushing and not researching more thoroughly. Needless to say next time he'll just filter a hell of a lot more and then basify with NaCO3 rather than disolving in alcohol.

 

[endlessness]

are harmalas soluble in naphtha? does harmala red form when evapping naphtha with harmalas? does freeze precipitation work with harmalas and naphtha?

 

[69ron]

As I said above, The Chemical Gazette says harmine is slightly soluble in naphtha, so naphtha would not be a good solvent to use. I've never heard of anyone having success using naphtha, heptane, hexane, etc.

The XLogP3 of harmaline is 1.2. That's way too polar for extraction with naphtha. Harmine is much less polar than harmaline. The XLogP3 of harmine is 3.6, so if harmine is poorly soluble in naphtha, harmaline would be even less so.

 

[endlessness]

oh sorry i missed that post!

so when people say they do an A/B with rue, what kind of solvent do they use? xylene ?

SWIM is looking to find a way out of the filtering mess that this time is specially tough...

 

[69ron]

With harmaline being usually the main alkaloid (and the most potent) in rue, you really want to make sure it gets extracted along with the harmine (unless you don’t like harmaline).

Most texts books use diethyl ether, chloroform, or dichloromethane (DCM) to extract freebase harmine and harmaline from a solution of water basified to pH 10 with ammonia. I’ve not seen other solvents used anywhere.

Xylene MIGHT work. D-limonene MIGHT work. It would be very nice if D-limonene worked.

 

[endlessness]

OK so here's SWIM's procedure.

First he grinded 150g of rue with a coffee grinder



Then he added maybe 700ml of water in a pot, a bit of vinegar (didnt measure) and boiled for half an hour. Filtered using a course filter like an old t-shirt. He repeated the process for a total of 3x and in the end threw the solids away and kept the liquid.

He let it decant in the fridge overnight, poured off the top part and threw the bottom decanted part away. He put it back in the pot, reduced in low fire to 1 liter, and decanted once more overnight.

Then he again put back in the pot, just warmed up a bit and added pure sea salt (360g for the liter). Back into the fridge again overnight. Next day he threw the top liquid away and redissolved the bottom decanted bit with 1 liter warm fresh water.

Then he proceeded to add sodium carbonate until the solution stopped changing colour, as seen below. Notice the colour changing as the sodium carbonate hits the water:





SWIM had 2 containers, notice the difference in colour between the right one which he had already added the sodium carbonate, and the left one which he was just starting.





The colour changing means the alkaloids are precipitating. Check this close up picture of the glass, one can see tiny freebase harmaline/harmine crystals floating around already:





Then he left overnight in the fridge again. This time he poured out and threw away the top part, and he filtered the bottom decanted part. To filter, he used an improvised vacuum filtering system using a funnel and filter, an hdpe bottle, some tube and vacuum cleaner, as seen below:




This stuff is horrible to filter. One cant use a coarse filter, but typical paper filters always block. Even with vacuum he had to move the filter around a few times to get it working:




Also one issue is that, once its filtered and dried, to scrape the harmalas off the filter is a bit troublesome, as quite a bit is lost to the filter (or else one starts scraping fibers of the filter together)


Now everything is outside drying. There are maybe 2 different purities, one is lighter brown and the other bit darker brown. He thinks he might redissolve at least the darker stuff in acidified water and repeat the whole process, but this time having much less impurities to deal with so hopefully all the filtering and stuff will be much better. Also repeating the acid+salt+base steps, he hopes to end up with very pure stuff.

Here's the rue drying, one in a filter and the other on top of a plate:

 

[geeg30]

When using IPA and such, couldn't you just toss in some zinc to prevent the oxides - similar to what you do for DMT oxides?

 

[69ron]

This stuff is horrible to filter.

If only there was a good way to filter it. SWIM has tried everything and it's still a pain to filter. Even really good quality expensive glass microfiber filters with vacuum applied can take a long time to filter it.

Sometimes it’s not so hard to filter, other times is nearly impossible. Does anyone know why?

I’ve heard some people talk about roasting the seeds prior to extraction. That should break down mucilage. But does that also break down some of the alkaloids?

 

[69ron]

When using IPA and such, couldn't you just toss in some zinc to prevent the oxides - similar to what you do for DMT oxides?

Water is so much cheaper. Why bother to use alcohol at all? If you do you’ll want to use a free oxygen scavenger that is soluble in alcohol like vitamin C, not zinc. You’d want to add it to the alcohol before doing the extraction for best results. Vitamin C is a great antioxidant.

Here’s the solubility of vitamin C:

Soluble in hot water.
Partially soluble in cold water.
Insoluble in diethyl ether.
Solubility in Water: 1g/3ml water.
Solubility in water: 80% @ 100 deg. C and 45% @ 45 deg. C.
Solubility in alcohol: 1g/30 ml alcohol.
Solubility in absolute alcohol: 1 g/50 ml absolute alcohol.
Solubility in glycerol: 1g/100 ml glycerol.
Solubility in propylene glycol: 1 g/20 ml propylene glycol.
Insoluble in chloroform, benzene, petroleum ether, oils, fats, fat solvents.

 

[prottel]

I’ve heard some people talk about roasting the seeds prior to extraction. That should break down mucilage. But does that also break down some of the alkaloids?

I don't think that degradation would be a problem. It is easy to try.

harmaline had a mp 242–244 °C (with beginnings of sublimation at 189 °C)

 

[endlessness]

yes its a pain to filter! SWIM thinks that the best way is always to decant as much as possible, then redissolve the last bit in more water and do all the steps like this, repeating all the steps a few times.



SWIM got 7g of impure harmalas out of 150g seeds. It looks quite brownish but it has a shiny cristally touch to it. Last time he took something similar he used 300mg and was enough MAOI for him. But this time he wants it cleaner.



He redissolved everything in vinegar acidified water again, will let decant overnight, then repeat the whole thing, salt precipitation and then sodium carbonate freebase precipitating. He hopes he will get rid of most of the crap and that the final step will be much easier to filter than now the first time. Even if he loses half of it, but its clean stuff, he will be very happy.




(btw ron, I accidentally clicked edit on your second-last post instead of clicking the 'reply' button, so I posted on top of your message. I think I put it back as it was, but maybe I left something out, sorry about that)

 

[69ron]

(btw ron, I accidentally clicked edit on your second-last post instead of clicking the 'reply' button, so I posted on top of your message. I think I put it back as it was, but maybe I left something out, sorry about that)

You can edit my posts? What the heck?

 

[T]

This stuff is horrible to filter.

If only there was a good way to filter it. SWIM has tried everything and it's still a pain to filter. Even really good quality expensive glass microfiber filters with vacuum applied can take a long time to filter it.

Sometimes it’s not so hard to filter, other times is nearly impossible. Does anyone know why?

I’ve heard some people talk about roasting the seeds prior to extraction. That should break down mucilage. But does that also break down some of the alkaloids?

You could try leaving the seeds intact, most of the alkaloids are in the husk anyway.
I've just finished an extraction where I've boiled the seeds once without grinding, and had 3.1 grams of freebase at the end for 100 grams of seed and the filtering was quiet easy.

 

[endlessness]

Now the process got much nicer

So SWIM redissolved 6g of brown impure harmalas in 1 liter of warm water+vinegar, and let decant overnight. Quite some dirt fell to the bottom. So he poured the top part out, and he filtered the bottom part (was not so bad this time) and threw away. Then he had a very nice clear liquid to play with.

He warmed up the clean reddish colour liquid and added 360g salt. It all changed to a more opaque cream colour. Quite a bit of the salt did not dissolve, but he was not worried as later on he would get rid of it again. He let decant overnight in the fridge. Here's how it looked:






It had a quite beautiful transparency to it. Some of the harmalas stayed on the top, so SWIM just filtered the whole thing. This time filtering with his improvised vacuum contraption was much easier. The filtered hcl harmalas + salt looked light brown with some yellow tint. He didnt dry it completely as he would redissolve in more water anyways. here's a pic:





Then SWIM redissolved the harmala salts in warm water. The colour changed to this beautiful translucent red.





He then added maybe a couple of teaspoons of sodium carbonate, and the colour changed immediately, very beautiful transformation somehow, first yellowish then to this creamy opaque colour, as the harmalas precipitated as freebase.






He let decant overnight. The liquid was bright and transparent fluorescent yellow, and on the bottom there was a nice light brown/grey layer of the freebase harmalas. here's how it was looking:




Now he filtered (was very easy with his improvised vacuum filter) and is letting dry. It looks light brown, when its dry he will take pics. Maybe nothing like some perfect white crystals like dmt, but he is very happy as he know the whole process was with safe products, no weird chemicals, and he can ingest happily and have a nice pharmahuasca trip at some point

Specially this second time around when he repeated the whole process with the crude harmalas, it was very nice to work with, the colours were changing beautifully, the filtering was easy. SWIM enjoyed this

 

[The Traveler]

(btw ron, I accidentally clicked edit on your second-last post instead of clicking the 'reply' button, so I posted on top of your message. I think I put it back as it was, but maybe I left something out, sorry about that)

You can edit my posts? What the heck?

endlessness has just been added to our moderator team, you can read it in this post.


Kind regards,

The Traveler

 

[bluejay]

Excuse me but I am not breakin any fda rules.....I stated it hasnt been approved by them..Its a herbal supplement..use at your own risk...

Ebay pulls it once and a while and I just remind them that it is not a federal scheduled item ,they have no reason to, they relist it within a few hours..thats why I started harmalashop.com..

I put alot of working into producing it and love working in my lab so I wont give out to much info..Sorry....

Some of you are o n track though....

Crystals with mary are a-w-e-s-o-m-e.......

I supply harmaline cheaper than anyone on line and will always give the best service and product..

 

[69ron]

This stuff is horrible to filter.

If only there was a good way to filter it. SWIM has tried everything and it's still a pain to filter. Even really good quality expensive glass microfiber filters with vacuum applied can take a long time to filter it.

Sometimes it’s not so hard to filter, other times is nearly impossible. Does anyone know why?

I’ve heard some people talk about roasting the seeds prior to extraction. That should break down mucilage. But does that also break down some of the alkaloids?

You could try leaving the seeds intact, most of the alkaloids are in the husk anyway.
I've just finished an extraction where I've boiled the seeds once without grinding, and had 3.1 grams of freebase at the end for 100 grams of seed and the filtering was quiet easy.

SWIM tried it that way and didn't get a good yield. Are you sure about that?

 

[T]

This stuff is horrible to filter.

If only there was a good way to filter it. SWIM has tried everything and it's still a pain to filter. Even really good quality expensive glass microfiber filters with vacuum applied can take a long time to filter it.

Sometimes it’s not so hard to filter, other times is nearly impossible. Does anyone know why?

I’ve heard some people talk about roasting the seeds prior to extraction. That should break down mucilage. But does that also break down some of the alkaloids?

You could try leaving the seeds intact, most of the alkaloids are in the husk anyway.
I've just finished an extraction where I've boiled the seeds once without grinding, and had 3.1 grams of freebase at the end for 100 grams of seed and the filtering was quiet easy.

SWIM tried it that way and didn't get a good yield. Are you sure about that?

No.
I weighed my yield again and it seems it was not completely dry first: it's only about 2.4 grams + I used a little.

I remember reading somewhere that the husk contains most of the alkaloids, I tried to find the same webpage but I couldn't. However:

according to Wikipedia most of the Harmala alkaloids are in the husk, but I trust this info better:

In the course of the study of germination metabolites of Peganum harmala seeds, it was found that the alkaloidal constitutents are wholly located in the husk of the seeds to the extent of upto 7%. On the other hand the kernels which form about 50% of the whole seeds yield 20% of an oil which is completely free from the toxic alkaloids and compard in its physical data with cotton seed oil.

From here: Pakistan Science Foundation

My current yield is very poor indeed but this was my first go and I was messing around with it quiet a lot. I will try it again, with whole seeds, boiling it longer (they seem to swell which is good) and maybe using a lower ph.

How acidic the solution can be without damage?
Is it okay to skip the salting and basify with sodium or calcium carbonate to get all the alkaloids to precipitate?

 

[endlessness]

how clean are your alkaloids? What process did you do, acid boil, manske and then freebase precip?

 

[T]

how clean are your alkaloids? What process did you do, acid boil, manske and then freebase precip?

I slow cooked them (100g in 1.5 litres of water) for about an hour with citric acid (ph ~3 if I remember well), filtered many times with ease and boiled it down to about 300ml. Started to basify with ammonia. Seeing the milky drops forming I got scared:shock: (didn't know that it was supposed to look like that) and salted instead. I got a gel like substance in the fridge so I added some more water. After 2 days collected the freebase and washed till the water was light yellow. The freebase is light brown, in the form of brittle granules that brake down into a very fine powder. I don't know how clean they are.