Hey guys. I wrote this in notepad before even joining the site. I was going to post it in the "harmalas" section, but apparently I cant do that yet. Maybe someone important could move it later. Sorry, its a bit wordy.
I recently attempted my own harmala alkaloid extraction on the seeds of syrian rue. I have had some seeds lying around for almost a year, and only just learned that the extraction was easy and I already had the right ingredients. (Im talking about manske). I kind of made it up as I went along though, taking semi-regular notes.
At the end of the process, I am left with this dry dark brown powder.. Rust colored even. I believe it is at least partly composed of the desired alkaloids, but I do not have a way to accurately do a MP test or anything. I read somewhere that ethanol can convert harmaline to "harmaline-red", and no one seems to know what the implications of that are. I was afraid I might have done this using my procedure - when adding alcohol to the filter paper immediately darkened the solution I was already very suspicious. But my extract looks very similar to the picture on erowid (http://www.erowid.org/chemicals/show_image.php?i=harmala/harmala_extract_powder__i2005e0425_disp.jpg), so that is a little bit reassuring.
However, from what I read, It seems that I would have had the perfect conditions for the appearance of harmala-red (I mean the last step where I purify with dry EtOH), and I believe I do indeed have some of this in my product. I am not fully convinced yet that h-red is actually a breakdown product of harmala and not some unrelated compound in the seeds. AFAIK everyone here is using harmala derived from seeds.
So The only thing left for me to do was a bioassay. The results... It definately has some MAOI effect.
My lab notes from today are below. Read them first (tldr version: I made some red extract using ethanol and when I ate it it seemed to work alright)
My questions to everyone:
1. Whats the best way to purify the extract I have. I was thinking of going to freebase/nonpolar and then back. I have NaOH if that would help.
2. Would methanol cause this reddining effect? Acetone?
3. Why does everything call for non-iodized salt?
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Syrian Rue Alkaloid extraction using acetic acid and sodium chloride
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Materials:
> 50g syrian rue seeds
> 2 pounds non-iodized pickling salt (listed ingredients: pure salt)
> 5% vinegar
> 26er of my moonshine (homemade distillate of fermented sucrose, double distilled, nearly absolute). Probably should have used methanol.
Equipment:
> A small electric grinder
> A few beakers or Erlenmeyer flasks, 250 and 600ml. Bonus if they are graduated.
> A canning jar with screw-top lid
> 1000w electric heat source (I put my beaker directly on an electric stove)
> Turkey baster, helps for decanting
> coffee filters, and something to hold them (like a funnel)
- Took ~50g of Syrian Rue seeds, and crushed them fairly well using a coffee grinder
- Added straight vinegar, about 250ml. left overnight in the canning jar.
- Decanted the vinegar solution with turkey baster (only about 50ml was avaliable on top of the rue sludge), added 250ml more vinegar to the jar with the rue, mixed, and decanted that as well. Added 250ml of vinegar to the rue again, and left it to steep.
- Took the 300ml of rue-vinegar solution, and tried to coffee filter it with moderate sucess (clogged, gave up)
- Heated it up in the microwave until it was probably about 60 degrees C.
- Added an excess of coarse salt (maybe 1 cup), stirred for 5-10 minutes, and quickly decanted solution from the undissolved salt
* The brown liquid had gone opaque as the salt was dissolving, presumably this is alkaloids precipitating out.
- Solution settled at room temp for 12h. The solids settled into a layer at the bottom that was approximately 120ml in volume. It was a light brown/tan color. The top liquid was murky but translucent, and darker brown/amber in color. Top layer of liquid is mildly fluorescent under CFL lighting.
- The top liquid was decanted and discarded.
- 400ml Cold, saturated salt solution (CSSS*) was added to the solids to wash them. They were allowed to settle 12h. The top solution (which was fluorescent, somewhat cloudy and a yellow/brown color) was discard.
- 400ml CSSS was added to the solids, this time it was coffee filtered in the fridge. The discarded wash was yellow.
- A final wash of 200ml CSSS was added to the filter funnel containing the solids in two 100ml portions, allowing each one to run through completely. Filtration was done in the fridge. At this point the solids are still a light tan color. The wash is nearly clear (also fluorescent), but everything still smells like vinegar.
- Tried to separate the alkaloids by washing them through the filter using ethanol (near-human grade ultra-high proof moonshine. mostly ethanol, estimated 92-95%). This plan was aborted when the ethanol turned a much darker color than the solids. Instead, put the now dark red-brown ethanol in a beaker, washed the rest of the gunk from the filter into the beaker using water (volume:200ml), and boiled off all of that to obtain a brown powder. The liquid got darker and darker until it formed into a paste. This was put in a double boiler until it was a dry powder.
[In retrospect, I probably shouldn't have done the all that extra work, and just proceeded with the moonshine..]
- The extract at this point weighed approximately 9 grams (20% of original mass). Presumably it had a high salt content from crystals that had formed in the CSSS. It was a brown color, kind of closer to dark brown. It tasted bitter and salty. A small sample was not particularly soluble in water, although ultraviolet light proved that it definately is to some extent.
- 50ml moonshine was mixed with a large excess of iodized sea salt (didnt have non-iodized today) and stirred vigorously. This ethanol was coffee filtered to obtain "pretty dry, but kind of salty ethanol". This step may not be necessary, or else it should be preformed with magnesium suphate annhydride (?).
- the 9g of powder was mixed with 50ml of ethanol. The solution quickly became a deep reddish brown color. It was heated in the microwave to boiling to encourage the alkaloids into solution (bad idea?). A lot of solids did not dissolve, which was expected. Although deeply colored, the ethanol solution was completely transparent and strongly fluorescent in the sunlight.
- The ethanol solution was double-boiled to obtain 1.5 grams of dark brown powder (darker brown than before, rust colored). This material is at least slightly soluble in water, small amounts turning the water a shimmery off-green/brown color, which dyes anything it touches fluorescent yellow.
The material tastes bitter, but not overpoweringly so. It is not detectably salty.
If this substance is actually mostly beta-carbolines, then the yield was 3.0%.
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* Cold Saturated Salt Solution
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1. Boil a liter of water
2. Add about a pound (360g, but more is fine) of non-iodized coarse pickling salt to a large glass container
3. Stir for 5-10 minutes or until no more salt dissolves.
4. Decant the solution from the remaining salt. Discard the salt.
5. Refrigerate the solution to 5 degrees Celsius, and then add one pinch of salt to make sure the solution isnt supersaturated. Sometimes you can watch cool crystals grow
6. Decant the salt solution off of any remaining salt crystals. Dont bother trying to get every last drop, its just salt water.
Keep refrigerated so its cold when you want to use it.
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Trip Report
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T minus 2h. I took 16mg of ephedrine, as I usually do on most days.
9:40 weighed out 50mg of the above extract, and began placing on my tongue and dissolving it there. It tasted just slightly of salt, and was bitter. Not very tasty but not hard to suck on. It made my tongue numb. I took about half an hour to slowly eat the whole amount.
10:30, its been 50 minutes since I started and I definately feel "different". slight dissociation, things seem to be going a bit slow. The familiar feeling of coming up on a hallucinogen. I would say I am at +. My tongue is still a little numb.
10:40. I ate some bread, had a drink, and downed 80 more mg of extract in a gel capsule. I am going to make a small amount of DMT (mimosa h.) tea to test the MAOI activity.
11:02. still feel the same, no increase or decrease in effects. set 7g of bark to steep in lemon-water. Did not attempt to bowdlerize it or boil it. Its just tea. Put 20 more mg of extract in my mouth as well
11:34. Now I am feeling it more! I am up to 200mg of extract. I feel a pleasant euphoria. I am awake and stimulated despite it being close to my bedtime (2am). I want to take more time and explore the properties of the harmala alone, but I also want to see if DMT works at this dose level. Fuck it, I put 50 more milligrams in my mouth and begin sipping the tea...
11:39. the 50mg extract is actually still all in my mouth. its numb.
11:45 actually start drinking mimosa tea. it is quite tart, bitter
11:57. Half the tea is gone. Im enjoying myself (id say I finally hit ++), but absolutely no visuals yet. Im getting pretty full and I dont want to vomit later...
12:01. suddenly, I feel like the DMT is present. The words on my screen just started flowing. Did I always have a slight audio buzz or is it getting louder?
12:07. It is unmistakably DMT, but I cant finish the second half of this tea.
12:14. I feel kind of sick, kind of tired. Detailed colorful CEVs
12:20 I force the rest of the tea down in one go
12:30 I have been sitting outside with my eyes closed for the last 10 minutes, but the nausea kept increasing and I was not able to enjoy myself. Recognizing the point of no return and unable to fight it any longer, I puked up everything in my stomach.
12:33 My mouth tastes like shit but at least I dont feel sick anymore. I have to clean up my puke bucket.
12:44 The experiment is pretty much over so I will smoke some pot. The whole puking experience brought me down a lot. Clearly the root bark of mimosa contains some very irritating substances. I will do a full DMT HCl extraction next time?