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Jungle Spice: Mystery Alkaloids of Mimosa Root Bark


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#1 Entropymancer

Entropymancer

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Posted 05 March 2008 - 10:50 PM

Ask and ye shall recieve... This is a work in progress over at the DMT-Nexus. Several members here have expressed interest, so I'm
putting it up the current draft here for the Topiates to enjoy. It's gradually growing, and will probably be done in a few weeks (around Spring break), but I'll be posting new material as I put it together on the copy hosted at DMT-Nexus (link below). Once it's done, I can re-post here.


"Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark




Synonyms - Jungle DMT, red spice, red DMT, dark spice, dark DMT, etc.

(Alright, this post will be under construction for awhile as I sort through the rest of the information that's out there and get this stuff written.)

(The wikiscipt is having trouble with links that have "MHRB" in the address)


So just what is Jungle spice?

Jungle spice is one of many names that has been applied to a particularly intriguing non-DMT alkaloid fraction which can be isolated from at least much of the commercially available Mimosa rootbark (See Botanical Confustication). In the most general terms, it is the alkaloid fraction obtained from the aqueous basic phase of an extraction by pulling with xylene or toluene after DMT ceases to be pulled by an aliphatic hydrocarbon solvent (naphtha, heptane, etc.). This product will almost always contain some degree of N,N-DMT; some extractors choose to remove the DMT in a hot naphtha wash to obtain a pure "jungle" experience, while others use the jungle/DMT mixture as it is.

There is a great deal of ambiguity surrounding jungle spice, owing to a wide array of factors. First and foremost, there appears to be a great diversity of compounds which can be isolated by extracting the aqueous basic phase with xylene or toluene. What compounds are actually isolated depends on some several of the following factors: minimum pH, maximum temperature and duration spent at this temperature, maximum pH and duration spent at this pH, and whether a fan is applied in the evaporation of solvent. On top of that, there's strong indications that some or all of the isolated compounds oxidize and change activity based on duration of time the material is allowed to sit at environmental conditions after extraction. And as if those things weren't enough, we also have to account for the fact that it's essentially impossible to know exactly what species of Mimosa the extracted rootbark came from. About all that is certain about it at this point is that it isn't N,N-DMT.

There has been a lot of speculation going around that this compound may be yuremamine, the novel phytoindole isolated from Mimosa tenuiflora and characterized in 2005. Looking at the evidence this appears to be exceedingly unlikely, based on yuremamine's known instability to acid, apparent instability to base, and speculated instability to heat. It certainly cannot be ruled out completely at this point, but there remains a substantial body of evidence against it. Until a GCMS of jungle spice emerges with a molecular ion at 477.1 m/z, I think it's safe to assume that yuremamine is not the red alkaloid that has been isolated by home extractors.

That said, I hope that the ensuing analysis can shed some light on the subject.



Table of Contents
I. Diversity of the Extracted Compounds
- I.1 Red/Brown Crystlline Goos
- I.2 Tan Waxes
- I.3 Yellow Oils
- I.4 "Kokusaginine"
II. Experiences
- II.1 Experiences Smoking the Red Crystalline Goo
- II.2 Experiences Smoking Tan Waxes
- II.3 Experiences Smoking Yellow Oils
III. Isolation Techniques
- III.1 Critical Switch's Tek
- III.2 Implant's Isolation of "Kokusaginine"
- III.3 Entheogenist's Jungle Tek



I. Diversity of the Extracted Compounds

Probably the biggest issue complicating the issue of jungle spice is the sheer diversity of compounds that can be extracted using roughly the same method. Based solely on physical properties, we can classify three distinct types of material that have been extracted as the endproduct from a xylene/toluene pull. When we consider the reported pharmacological activity of these materials in human subjects, the picture becomes much more comlicated; this issue will be dealt with subsequently.

I.1 Red/Brown Crystalline Goo


Figure 1. Red/brown jungle spice goo from Critical Switch Tek (left), another specimen (right)

"After doing two pulls with naphtha I did two pulls with toluene, evaporated the toluene, and washed the solids with naphtha which made them dark red."
Entheogenist

"Could you describe the material? My friend's has the consistency of a soft crayon and is brick red."
Noman

"The junglespice I got is just like a peice of a red crayola crayon. After evapping it looked like crystals on the dish, but when scraped up with razor blade it all stuck together to make this waxy homogenous stuff. It has a strong smell of indole when burnt, but otherwise it has a similar smell to DMT, but with a fruity kind of a smell."
QuantumBrujo

"Swim succeeded in pulling the red spice. Its a dark , deep crimson color , almost the color of dried blood."
Spicemeister



The reddish brown crystalline goo that one can find pictures of floating around the internet are what I tend to think of as jungle spice, but washing this goo can yield a surprising diversity of products. As the above quotes indicate, washing the dark gunk with naphtha yields a red solid which is insoluble in the naphtha (Figre 1). This red material has been isolated both by straight-to-base extraction (Noman's) and by acid/base extraction (Marsofold's tek).

The crude extraction is invariably an impure mixture. In most cases, the crude xylene pull from the basified aqueous phase is a bright yellow color; the red pigment cannot be seen until the solvent is evaporated. When the DMT is removed from the crude extract by a warm wash in an aliphatic hydrocarbon (naphtha, haptane, etc.), many extractors report that the recovered DMT crystals remain stained yellow. It is this yellow fraction that is soluble in warm naphtha that I identify as the yellow oil component of jungle spice (see Yellow Oils).

It is important to note that some people obtain an explicitly brown goo from the xylene pull, with no real indication of red coloration whatsoever (Figure 2). Although they may appear appear similar on initial inspection to the crude red/brown goo, crude extracts which are exclusively brown appear to contain a different active principle, totally distinct from the red material. The lighter of the two tan waxy specimens (Figure 3) is the final product that was obtained from Figure 2 after the goo was washed with hot naphtha.


XenonsionPrePdt.jpg
Figure 2. A brown goo lacking any reddish tint



I.2 Tan Waxes


Figure 3. A couple of tan waxy specimens.

"[A] xylene pull of a basified acidic extract of this material yields a crystalline slightly orange waxy substance that smells of tryptamines and glows orange under a blacklight."
Archaea

"[E]nded up with tan waxy non oily stuff that is stronger than hell (10-20 mg) and terrifying. It's not just residual DMT, its too strong for that."
Noman



The name and the pictures say it all. This fraction is a very waxy solid, with coloration ranging from a light yellow/orange to a much darker brown. The exact color of this fraction appears to be highly variable from extraction to extraction. It is obtained in essentially the same way as the red material above; an aqueous hydroxide solution containing mimosa alkaloids is extracted with volumes of naphtha until no more N,N-DMT is pulled. The spent solution is then extracted with a few volumes of xylene or toluene to obtain a product varying from light yellow to dark brown. Washing this crude material with hot naphtha yields a waxy orange solid.

As far as I know, this material has never been isolated from a straight-to-base extraction. It's isolation has also been positively correlated with doing heated naphtha pulls to remove the spice prior to diong the aromatic pull, but it's not clear at this point whether this is simply coincidental. Again, we'll run into some further confusion when we look at the reported pharmacological activity of this isolate, indicating that there may be more than one compound comprising this fraction. Specifically, this is the fraction of jungle spice which is most frequently reported to change activity over time, indicating some chemical reaction (presumably ocidation) is occuring.


I.3 Yellow Oils

Figure 4. Two samples of DMT containing significant yellow impurities, courtesy of Erowid.org

"The yuremamine which was evaporated out of the filtered xylene defat of the powdered root bark was a yellow creamy color prior to purification, and a translucent orange-colored almost oily residue which would not dry to a hard substance."
Lycaeum Member

"It's yellowish. Even a yellow crystal. Smells the same as dmt with a musty overtone."
Heyoka

"After two recrystallizations on the N-N that came out with [the jungle spice], swim tells me it is irretrevably stained yellow and resembles egg yolk."
Spicemeister



This is by far the most ambigous fraction that comes out of the xylene/toluene pull. Some of the yellow oils that have been isolated from Mimosa have been speculated to be plant fats and oils; another fraction of yellow oil is suspected of being an oxidation product of DMT.
To further complicate the issue, it's very difficult to isolate the yellow oil on its own; in addition to being soluble in xylene and toluene, it is also quite soluble in hot naphtha. This is evidenced by the fact that many people doing otherwise normal extractions report obtaining a yellow-colored product when the naphtha pulls are done heated. These yellow crytals are usually reported to be qualitatively better in terms of effects than pure DMT. Also, when washing the crude jungle spice extract with warm naphtha, many extractors report that any N,N-DMT they recover from this process is strongly yellow-colored. Unfortunately I haven't been able to find any experience reports using the yellow spice isolated from the darker jungle spice, so there's absolutely no evidence for claiming that these two yellow oils are in fact the same substance, although they very well could be.

Investigating the possiblity of the yellow oil being DMT N-Oxide, I found a 2005 paper reporting its isolation from a methanol extract of Acacia confusa, but it contained no description of the physically observable characteristics of the compound (such as color), only the measured NMR data.

Looking at the Radio897's GCMS of a crude xylene pull of jungle spice reveals a peak at 205.1 m/z, which corresponds to the expected molecular ion of DMT N-Oxide, so it seems like a pretty good bet that this chemical is generated as a sideproduct of the extraction process, most likely in the aqueous basic phase. It may exist in the bark as a trace component (there is a barely perceptible peak at 205.1 m/z in the Vepsäläinen paper reporting the characterization of yuremamine), though it's possible this trace peak was an artifact of the isolation process as well. It's also possible that the sample analyzed in the paper was from a different subspecies, or even an entirely different Mimosa species than is typically purchased as rootbark (see Botanical Confustication


I.4 "Kokusaginine"
When browsing around threads discussing jungle spice, inevitably you start running across people claiming that kokusaginine is likely the chemical responsible for Jurema's reported oral activty. Generally these posters cite the 1999 Entheoegen Review article where Jonathan Ott and K Trout are asked their opinions on the matter. Unfortunately, these people apparently read no further than the second paragraph before leaping to this completely unfounded conclusion. To summarize:

The article begins with a question from someone identified as J.S, OR.

Jonathan Ott seems to think that Mimosa hostilis is active without MAOI added. The ingredient, kokusaginine, which is morphine-like in structure, may possess MAOI properties... I would suggest that the kokusaginine, supposedly insoluble in water, is nonetheless extracted enough...
Does anyone know, for certain, what the effects of kokusaginine are?


The Keeper of Trout was asked about this, to which he replied

I have only heard of kokusaginine reported from the Rutaceae. I know nothing about its activity except for the fact a related compound was reported to be antagonistic to Ditran... I did notice a very strong stuporous component with one bioassay of M. tenuiflora root-bark and a MAOI, that I did not in the others. Jonathan would be the best one to talk with about this.


So the folks at Entheogen Review asked Jonathan, and here's what he had to say:

I've no idea whence derives the querist's notion that kokusaginine occurs in M. tenuiflora, and I am in agreement with K. Trout's remark in this regard, while it is a mystery to me why it would be assumed this compound possesses MAOI activity, nor indeed how this compound-or moclobemide, with which it is structurally unrelated- is "morphine-like," none of which has anything to do with the recondite pharmacology of jurema preta/ tepescohuite, in any case.
Perhaps there is some confusion here between the rutaceous kokusaginine [found in New Caledonian Dutaillyea spp., among others] and the socalled "kukulkanins" reported from powdered stem-bark of Mexican tepescohuite [misreported as Mimosa tenuefolia L. (sic): Journal of Natural Products 52(4): 864- 867, 1989], also of obscure pharmacology. There is no reason to suppose this compound or any of the diverse saponins likewise reported from bark of Mexican tepescohuite show MAOI activity, and at least five phytochemical analyses of Brazilian jurema preta [mostly unpublished] have failed to show presence of ßcarbolines nor any other category of potent MAO. Moreover, pharmacologically and pharmacodynamically, the psychoptic effects of cold-water, hand squeezed and short-time-infused, aqueous extracts of simple pounded jurema preta root-bark prepared according to the traditional manner as documented in several Brazilian reports, bears no relation to the-to me-well-known pharmacology of the ß-carbolines and other MAOI...
Preliminary chemical evidence reveals rather the presence of several novel and yet-unidentified DMTadducts in jurema preta root-bark, apart from free DMT itself. Either these compounds show oral activity per se, not being substrate to gastric MAO, or rather show a higher affinity for the enzyme[s], serving thus as competitive inhibitors respective to DMT for its active site[s], in the manner that the ß-carbolines do. My current work strongly suggests the former conjecture is the more parsimonious.


It'd have been nice if Mr. Ott explained why he feels the former explanation to be more parsimonious, as the isolation of yuremamine, with its intramolecular H-bonding, would tend to indicate the latter explanation. Regardless, I hope that this can put to rest the idea that the soporific component that has been isolated from Mimosa rootbark is kukosaginine.

Based on physical descriptions as well as reports of its effects, the compound that people have called kokusaginine is a variety or the tan waxy specimens, usually described as being very hard. Particularly with this fraction, it's been reported that as the chemical ages, the stuporous effects dissipate, and are replaced by a fully psychedelic activity profile.

For an account of the isolation of this fraction, see Implant's Isolation of "Kokusaginine"



II. Experiences

II.1 Experiences Smoking the Red Crystalline Goo

EASY DOES IT. 10-15 mg's of this stuff is insanely potent and just a bit more scary/intense than N-N DMT.

I took 3 full tokes from the red oil, the effects were a lot like regular DMT but there was something different. It seemed to be missing the loveing presence, the "other place" halucination was there but the colors were not, or at least they were very dark & dull.
My friend & I both felt like we would much rather stick to the regular, definable, loving, white DMT.

There is a distinct difference between DMT and the red spice for me. When smoking DMT, I want to smoke as much as possible, but after a few puffs, I was completely revolted. The anxiety and intensity of DMT was not present, but it was very odd and frightening. It's flavor was a spicy barbecue sauce, which was more or less tolerable. The effects of it were much more subtle with an 'easing in' instead of a blast off. The room became twisted, a more grotesque version of itself, some out of Nightmare Before Christmas. It felt like a graveyard and that I was alone (in a bad sense), but then some beings started to appear. They were black, fuzzy balls of energy, about 1'5'' tall and 1' wide, with an aspect of children. They were quite friendly and investigative of me (like children). However, the experience made me draw up into myself and I was quite dissatisfied with the feelings. I would like to note that subsequent DMT use (30 min-ish later) brought me up to a BAD part of the 'city,' with clown (not jester/joker-ish) beings of intense negative emotions and ideas who did not like me at all. They also beat up my Guardian when he tried to protect me from them.

This Red Jungle Spice is THE BEST THING I HAVE EVER SEEN. Terence McKenna MUST have been smoking the jungle spice thinking it was DMT. I've smoked alot of DMT and read alot of Terence Mckenna, and I have NEVER seen anything like what he describes. But, two tokes of this red jungle spice and I had his trip WORD FOR WORD. This stuff is SOOOOOOO much better, stronger, deeper, more meaningful, and more pleasant to use than DMT.
Editors Note: Terrence McKenna described DMT as "something that looked like orange mothballs" when recounting his first DMT experience, which appears to substantiate this notion.
I smoked it with my eyes open while watching SHPONGLE on stage. The stage began to morph and change, and suddenly a Self Transforming Machine Elf ripped the stage in half and jumped out to dance on top of the ravers. He was made out of what looked like shiny glossy molded plastic like a kids toy, but he was so colorful, changing shapes and dancing. This was with my eyes open. I had my rational mind intact; I knew I was at a Shpongle show smoking jungle spice. I could not believe my eyes. I even squinted at the stage in disbelief, trying to make things return to normal. If you smoke it with your eyes open, it completely transforms reality before your eyes. This is absolutely the most amazing chemical I have ever encountered, and everyone at the shpongle show agreed with me. I passed out about 3 grams of the stuff in individual doses, and evenryone agreed that it just blows DMT out of the water.
The second time I smoked it I closed my eyes. I was shot like a laser beam into God-consciousness. I was GOD. I created the universe and spawned life on earth. I saw the beginning and the end and everything inbetween. I beheld every thought that had ever existed in one instant. then I came back to reality and was back at the rave. BUT, I still thought I was God. I was walking around telling people I was the reincarnation of Jesus, Buddha, Terence McKenna and Tim Leary rolled into one. I truly believed this at the time. I felt omnipotent. I knew everything. But this began to fade and I started to feel stupid for walking around saying I'm Jesus and believing it. So then I started experiencing karma. I left the concert area and hid in the dark to meditate. I thought the people at the rave were going to crucify me. I thought they had already killed my son and were coming for me. I accepted this though, and embraced my imminent death. I knew I was going to die that day and it was OK. It took aboout 30 minutes for the jungle spice to wear off, and by that time I was a new man. My ego had been lifted up to the point of thinking I was a walking GOD, and then it was crucified. This stuff makes DMT look downright boring.

I'm traveling through their world now. I cannot interact with them and they are not aware of me, but I can affect their environment. [They are] solitary, lonely beings, living out their existence. They are oddballs, such as one being is a floating bust of an angry man and another is a pastel red colored 'cat' with a bejewled back. This land was not overtly unfriendly, but definitely an uncomfortable place to be in. A short-lived experience due to purposeful grounding.

SWIM once made a batch of a reddish-brown dmt from MHRB- I'm not sure how but it was qualitatively different from the white-yellow from the subsequent batch of extract. At first it was her favorite colour to smoke over white or yellow, but as it aged, and became darker red, blacker, the effects did become "evil" ... opening only to black spaces, twisted hyperspace. It was as though the dmt in the red spice had deteriorated and oxidized, leaving mostly mystery alkaloids that were having a greater effect.


II.2 Experiences Smoking Tan Waxes

"The material is tan and has the consistency of wax without being oily. A friend was over and wanted to try it. Not wanting to yuk up my DMT pipe and thinking that the stuff was shit anyway, I threw a few crumbs on top of a bowl of bud, 20 mg max. I really figured that it would just mostly taste bad. My friend took a hit, fanning the bowl with a butane torch and then he passed it to me. The bud was still burning and I just hit the top with a Bic, figuring that he had gotten most of it.
PUT IT DOWN PUT IT DOWN PUT IT DOWN!!!!!! Fuck, I couldn't get rid of the pipe fast enough. I leaned back in my chair - Why did I do that? Fuckfuckfuckfuckfuck. NO NO NO I DO NOT WANT THIS I DO NOT WANT TO KNOW THIS!!! Please just let me out I'll never come back just make this stop.
I don't know what I was reacting to, I was aware of no sensory input, hallucinogenic or otherwise, just that horrible feeling of NONONO. That went on forever and an instant and then I started to become aware again of my body and myself and I opened my eyes trying to pull out of that horrid fuckhole. Nope. Horrid fuckhole out there too. I had that crazy DMT vision where everything is fuzzy and lit from within and exists standing apart in it's own dimension but rather than the jewellike beauty of each atom, I was aware of the ugliness and nastlness of every line, shape, color, and texture. Everything was made of puss and overlapped and falling and oozing and suffocating and vomiting on me.
I closed my eyes again and I became the uglines. I opened them and settled for just being suffocated by it.
Around this time my hearing came back on line and I realized that the Tool album that we were listening to was no ordinary Tool album but a direct communication to me to reaffirm just how rotten and horrible every aspect of existence is. This came not as a paranoid flash of conspiracy like on MJ or acid but just as a fundemental understanding - like info gained from mushrooms. How can this be? How? How did they know that I'd be listening to this exact song right now? Despair washed over me as I realized just how horrible and squalid a thing everything that I'd ever known or loved was.
The psychoactive was wearing off. I white knuckled it back, said goodnight to my friend, and went to bed. The next day, it was still there. Nothing overt, just wearing a wet blanked of sorrow and despair about nothing. Beautiful things made me sad because I knew now what a lie it was. Nothing was nice. Everything had sharp teeth and wanted to bite.
The feeling faded over the day and now (T+2 days) I have to think about it to bring it back. But it's still there.
This could very well be merely a DMT trip gone bad. The substance was definitely used with inadequate preparation but I've used DMT under less than ideal circumstances before and never had it go that sideways. Such a small dose too. I'm sure that the total quantity in the bowl was less than 25 mg, my friend hit it first, I only had one toke, and in the morning I discovered that there was still some in the bowl. 25 mg of pure DMT doesn't get me as high as that shit did. It seems like it lasted longer than a DMT hit too, but I couldn't say for sure as I was too out of my mind to take note."

The effects of the "red" spice were body only, no visuals. However Swim found it very nice to put a nice chunk of the red behind the N-N in the pipe. Two large hits of N-N , and the third being the red. It seems to make the N-N extremely more potent, and much longer lasting. "Really nice effect"!!! Highly Reccomended, he said".

Swim once extracted some stuff using limonene and everclear that had no real psychedelic effect worth mentioning, but did have a long-lasting body high effect that felt really good, kinda like rolling or maybe a 10,000 X blue lotus extract or something. He smoked it with two chicks - he and one of the girls ended up falling asleep, while the other girl stayed awake for ~5hrs and continued to feel it the whole time. It felt good, but to use her words it was kind of like a "sinking spell."... he thinks this is the one people are mistakenly labeling kokusaginine.

The effects of K [yellow MHRB extract] are amazing to say the least ... swim has pulled it several times and everytime it has been the same... It changes radically with oxidation, becoming way more potent, and different, as time passes. If used within the first few days of pulling it (smoked ofcourse) it produces a heavy bodyload .. feeling like youve been shot with elephant tranquilizer.. lasting about 15 minutes. NO pronounced mental effects of any kind. However upon repeated exposure to air.. this substance .. given a few weeks is the absolute most "trippy" substance which he has ever encountered. Producing wild hysterical laughter .. massive size distortion in objects.. insane colorful hallucinations of things like cotton candy.. pink clouds.. puffy pink dragons and giant blue marshmallows. I know this sounds like total bullshit.. I probably wouldn't believe it either . It is true. It is very easy to find out. I highly suggest every try the K atleast.

The rock stuff swim pulled, what was considered to be kokusaginine carried only a heavy body load. After several weeks the substance got harder and harder, and darker in color. It also changed in smell. Swim smoked it maybe 5 times.. during the first week to week and a half after pulling it .. like he said.. only a heavy body load. No head effects.. nothing trippy whatsoever.
Well, swim tried it again when he was bored after a couple of weeks and found that it had went through some serious changes.. aside from the change in texture and color. It became really trippy... no real mental breakthrough or extreme DMT visuals or anything like that ... but it carried this INSANELY PLEASANT laughing .. singing .. trippy as hell load. No more heavy body effects. Swim smoked it on his bed .. took 5 hits ... had difficulty getting the 5th one because he was laughing so hard. The next thing swim knows, he is raising up and down off the bed like Linda Blair in the Excorcist, laughing his ass off in this INCREDIBLE "very tryptamine like" state. Lasted at least a half an hour .. swim winded up smoking about 20 hits over a 4 hour period and it was GREAT! Swim smoked all he had left the next night ... whatever it was it was phenomenal , wonderful.. !!!


II.3 Experiences Smoking Yellow Oils

There do not appear to be any experience reports by folks who've extracted and purified a yellow oil. However, due to the solubility of one (or more) of the yellow oils in hot naphtha, DMT crystals are often isolated with a distinct yellow discoloration (Figure 4), presumably because they contain the yellow oil in addition to N,N-DMT. There are experience reports with this substance, which I'll put here whenever I get around to it.

III. Isolation Techniques

III.1 Critical Switch's Tek

The very first tek known to describe the isolation of jungle spice was posted on Vovin's boards by Critical Switch. These boards have since gone down, and as far as I know the discussion of jungle spice that took place there has been lost. Fortunately Marsofold still had the tek. As he notes, it is needlessly lengthy, so I'll paraphrase a bit throughout. It also doesn't report pH at any point through the process, making it difficult to duplicate precisely. Further, it seems to be generally agreed upon that a more effective way to obtain jungle spice is to extract all the DMT with naphtha as usual, then do a xylene pull; this tek is included for historical relevance.

#1-9 - [Do an acidic extraction with hydrochloric acid]
#10 - [Basify the mixture with hydroxide.]
#11 Pulling the DMT from basified solution with Non-polar solvent - If you want the “jungle DMT”, then you will have to use xylene (lab grade or distilled). You will be performing three (or four if your obsessive) solvent extractions on each basified carboy... I swirl them every 5 minutes for an hour. Once this is done you need to siphon base solution out from under the solvent.
#12-13 [Notes on emulsions, sodium carbonate wash, construction of a homemade still]
#15-16 [Evaporate xylene and collect the dried product]
#17 Recrystalization is needed her for a few reasons. You can smoke the DMT as is but it will be a little worse tasting and the actual high is not as smooth. I put all the DMT into a flash and wash it with a nonpolar solvent until all that is left is a puddle of dark red. You now decant off the solvent and evaporate it or freeze separate it. Freeze precipitating will get a more pure product and this is what I will illustrate.
#18 JUNGLE DMT (Alternate Alkaloid)
You now decant off the solvent and evaporate it or freeze separate it to obtain the DMT. Freeze precipitating will get a more pure product and this is what I will illustrate. Now if you want the alternate alkaloid, the stuff you see in the flask above will crystallize and look maroon. This product is the jungle DMT alternate alkaloid and I advise you to take caution if you decide to try it. It won't work without using xylene or DCM as a extraction solvent. The washes must then be done with heptane or naptha to remove the DMT, but leave behind the alternate alkaloid, which forms bright red crystals once completely dried out as seen the picture.

#19 [Freeze-precipitate recovered DMT]



III.2 Implant's Isolation of "Kokusaginine"

As discussed above, this fraction is almost certainly not kukosaginine, but it is psychoactive. This isolation process is fairly unique in its use of a binary extraction solvent. From the available evidence, it seems reasonable to assume that this heptane/diethyl ether solvent is pulling a fraction which is also pulled by xylene or toluene.

As far as swim knows he is the only kitchen chemist who has suceeced in the extraction of Kokusaginine from MHRB (simply because no one else has tried as far as he knows). It is documented to be present in the bark by reputable lab research ...
Anyways its considerably more tricky to get this stuff. It requires the use of Diethyl Ether and heptane as a binary solvent, mixed "roughly" 8 parts DE/ 1part heptane. This is the solvent swim used to acheive success with this experiment more than once... You will also need naphtha and acetone.
You do everything you normally would to obtain your N,N-DMT except you use the binary solvent of DE&Hep. Freeze precipitation for crystallizing is a must here. Your spice will be "very" yellow. Some of this yellow tint is natural oils and fats .. some is oxidation caused by the extraction process and more still is "kokusaginine."
NOTE* The yellow you see if you used only naphtha is only the former two ... no kokusaginine will come out unless you use DE ! *
Pull all of your spice from the bark. Now you have a nice big pile of yellow spice. Time to recrystallize in the freezer and get your K. Pour all of your spice into the container which will be used for recrystallization... this needs to have an absolute flat bottom. Place it on the stove on its lowest setting (electric stove or hotplate only!), cover your spice with naphtha and proceed to dissolve it into the naphtha .. adding only 1 drop of acetone for every 10 ml's of naphtha you use. Add the acetone after the spice has dissolved into the naphtha . Make sure it is all dissolved and you have ample but not too much solvent . You should note a thick yellow oil looking substance coat the bottom of the container.. this is your kokusaginine. use a small dropper or syringe / whatever to remove all liquid solvent (which contains your dmt) and place in a seperate container for freeze precipitation.
Now you have a glass in which the bottom is coated with K . It takes forever to dry.. so before it does.. lets clean it a little further... drop some more naphtha on it.. while still hot (place back on stove if needed ) no acetone is needed here. Stir , stir , stir... traces of DMT will come out of the oil at this point and migrate to the naphtha which if you dont mind yellow spice.. put it in with the rest that you just removed. Ok so let this stuff dry in the bottom of the container... scraping it around helps tremendously... you should wind up with something hard as a rock.


III.3 Entheogenist's Jungle Tek

This process will not only produce very potent Jungle Spice, but it will also pull out any DMT that has been left behind in the basified solution.
After you have done your nonpolar extraction ala Noman's or Marsofold's TEK, save your basified solution. Now, for 500g of bark, use 500ml of Toluene. HEAT it in a water bath until it's steaming. Add the toluene to your basified jug and tilt for 5 minutes. It's best to divide the toluene into three or four pulls. While waiting for the layers to separate, put the toluene jar back in the water bath to keep it hot. After you have siphoned off the toluene layers, evaporate the toluene and let the solids dry. This material contains the jungle spice, but there is usually quite a bit of "regular" DMT also. Scrape up this material and put it in a test tube. (you can get test tubes and test tube clamps at hobby lobby next to the chemistry sets.) Now heat some Heptane/Bestine in a water bath and fill up the test tube with hot heptane and agitate the mixture until the heptane clouds up and an oily layer forms in the bottom of the tube. Let this mixture cool for a minute or two so the oily layer will thicken a bit. Now quickly pour off the heptane onto a plate for evaporation, making sure the oily layer stays in the test tube. When the heptane evaporates you should be left with pure DMT (you will want to recrystallize this product). Add more hot heptane and evaporate one or two more times until no more DMT is being pulled out. You should be left with a thick, deep red oil in the bottom of the test tube. This is your pure Jungle Spice. To get it out of the test tube, I first place the test tube in a water bath. This will cause the oil to pour more easily, and evaporate any remaining toluene. When it's nice and hot, remove the tube from the bath and immediately pour it out on a plate. (Some oil will still stick to the test tube, which you can rinse out with a VERY SMALL amount of HOT toluene and pour out for evap on a different plate. It will yield slightly less pure jungle spice.) The oil you poured off will slowly harden into a waxy solid. It takes quite a while to dry out, but you can speed the process by smearing it around with a razor, then scraping it up and smearing it around again and so on. Make sure all the toluene has evaporated before you bag this stuff, or it will turn to oil again in the bag. This Jungle Spice is VERY POTENT at 25mg, as opposed to 50mg of pure DMT. In my experiments, I have not found a way to purify it any further, but if anyone can refine this process I'd like to hear suggestions.




Molecules

Yuremamine.jpg
Yuremamine

ProposedYDP.jpg
A likely breakdown product of yuremamine, would have molecular ion at 350.1 m/z

DMT-N-Oxide.jpg
DMT N-Oxide


Mass Spec Data

RadioMS.jpg
Radio897's MS of an unpurified xylene pull, extraction process unknown.


MS of DMT reference standard (left) and Brazilian M hostilis A/B extracted at pH 1 (right)
(from Mambo Pachano's Entheogen Review Article - See Trout's Notes)

YuremamineGCMS.jpg
GCMS of Yuremamine (from Isolation and Characterization of Yuremamine)



Dark Spice Links

On the DMT Nexus
Dark DMT - The Other Alkaloid
Dark DMT
So I extracted the red DMT
Dark DMT Extraction
Red Spice Experiences
Doing Xylol Extraction
Yellow Oil = DMT N-Oxide?
On Ayahuasca Forums
Yuremamine - Solving the Mystery of Jurema Preta
Hummingbird's Brew
On the Lycaeum Forums
Dark DMT
On Drugs-Forum
The Other Alkaloid in Mimosa hostilis
Jungle DMT?
On the Nook
Extraction of an alternate alkaloid from Mimosa
On Entheogen.com Forums
MHRB H2O/MeOH Extract and TLC
Red Spice?
DMT Melted?
Orange Spice?
Mimosa bark active without ayahuascha[sic]?
MHRB, Yellow Oil, and DMT N-Oxide
On the Corroboree
Is it real M hostilis?
Jonathan Ott Articles
Mimosa Active Without MAOI?
Pharmahuasca, Anahuasca and Vinho da Jurema; Human Pharmacology of Oral DMT Plus Harmine
From Trout's Notes A-5: Ayahuasca - alkaloids, plants, and analogs
Jurema
--Reported Chemistry
--Isolation
--Preparation
--Synonyms and their Descriptions
--Other Mimosa Species


Pictures

th.4190520e1f.jpg
A Red/Brown Crystalline Sludge

Data - GCMS

Radio897's GCMS of an unpurified xylene pull, extraction process unknown.

Data - TLC

Dozuki's TLC Analysis

Attached Thumbnails

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  • XenonsionPdt.jpg
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  • RedspicerPdt.jpg
  • gcms_dmt.gif
  • erowid1.jpg
  • erowid2.jpg
  • ef700474b1.jpg
  • e1ed7f472e.jpg
  • 651f5fe606.jpg
  • CriticalPdt.jpg
  • 65b9d07b6d.jpg

  • i patch, Diacetyl-M, GodofOldGodsWatching and 1 other like this

#2 vinz

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Posted 05 March 2008 - 11:11 PM

very very helpful, this will clear up a lot of questions on jungle spice! :bow:
archive material

#3 Hippie3

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Posted 05 March 2008 - 11:17 PM

plz upload pix before archival.
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#4 Entropymancer

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Posted 05 March 2008 - 11:36 PM

I should also mention that if anyone has any idea how to get ahold of Radio897, or has any idea what sort of extraction process he was using, it would help greatly to put the significance of his GCMS into perscpective.

#5 vinz

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Posted 06 March 2008 - 04:37 AM

added in the pictures..

#6 ShroomGuerilla

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Posted 06 March 2008 - 11:16 AM

great info :pirate:

#7 antimatt3r

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Posted 07 March 2008 - 08:28 AM

interesting, im trying to understand, can you pull your dmt out of the mix, then go back and get some of these other spices, or do you have to choose which one you want all or nothing?

#8 mediciano

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Posted 07 March 2008 - 09:00 AM

school is in:eusa_clap
thnks for the great info

#9 Entropymancer

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Posted 07 March 2008 - 12:42 PM

interesting, im trying to understand, can you pull your dmt out of the mix, then go back and get some of these other spices, or do you have to choose which one you want all or nothing?


Yes typically people will do their spice extraction as usual, doing at least two or three naphtha pulls. Once the naphtha (or heptane, etc.) won't pull any more DMT, then you use xylene (or toluene) to pull the jungle spice.

This xylene almost always pulls some DMT that the naphtha missed along with the jungle spice. You can smoke this crude jungle spice to get a mix of DMT and jungle spice compounds, or you can use warm naphtha two purify it into two fractions, washing the DMT and yellow oil from the darker portion of the jungle spice.
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#10 Guest_floppypeter_*

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Posted 07 March 2008 - 01:45 PM

:headbang::bow::headbang:

#11 Entropymancer

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Posted 29 March 2008 - 05:30 PM

I.5 General Comments on "Colored Spice"

"So I'm wondering... The old-school heads at the festivals keep talking about RED or ORANGE DMT from back in the day, and how strong it was. I'm wondering if that old-school spice was actually just a mixture of the 2 alkaloids in one product... because as far as I can tell, pure DMT is white or clear crystals."

"I have had the orange DMT that Terrence and old heads speak of. It is DIFFERENT than the snow white DMT people extract these days. People will say things like "it's impure, clean it" blah blah blah. No. They've never had it then. It is the most ridiculously potent DMT SWIM has ever smoked."

"Since 1999 there has been the reds also called purple by some, yellow, orange, and white spices available at music festivals, and have been kept underground till recently. At the last SCI shows in Red Rocks CO there was all colors available, being offered quite openly.You could smell that sweet plastic smell every few 1000 feet while walking the lot."


There has been a great deal of discussion and speculation on "yellow DMT" and "orange DMT", some of which has been reported to be subjectively different than ordinary white DMT. This turns out to be a rather thorny issue. There are several unrelated factors that can lead to yellow or orange spice; sometimes these colored spices are reported to be more potent than DMT, sometimes less potent. The discussion will be organized based on the reported origins of the colored crystals.





I.5.A Old Spice

"The yellow oils oxidize to a ruddy-orange colour when stored at room temp for a month in a metal container. This is not good to let go any further, it's degrading as teh colour goes yellow to orange ... I have thought that this 'aged' yellow spice, that becomes 'orange' looks like what the T.McKenna’s spice must have been; a reddish and smelly mix oils and clear crystals... But beware! it keeps oxidizing and definately goes 'off'. It becomes blackish-rusty-red, smells different - when this happens it does not launch you... you get dragged behind the hyperspace shuttle... Bleah !"
El Ka Bong


Probably the simplest form of colored DMT comes samples that were originally pure white spice. As the samples age, they turn orange and waxy over time. There seems to be substantial disagreement over the amount of time necessary for this process to occur. Some people report a change in color become noticeable after several weeks to a month, while others have several month old samples that are still without discoloration. Anecdotal evidence indicates that higher temperatures speed this degradation process. It is unknown whether evironmental factors such as air moisture may play a role in the rate of degradation. It is likely that the amount of impurities initially present in the material plays an influential role as well.

Since this orange spice forms from fresh spice when exposed to environmental conditions for a long period of time, it is tempting to label it a simple oxidation product. Unfortunately, it's not quite that simple. We've already fingered a yellow oil as the most likely candidate for the simplest DMT oxidation product (DMT N-oxide). The orange color must come from something else, since a yellow oxidation product couldn't turn a translucent crystal orange. The simplest explanation that fits the available information is the following: When stored at room temperature for a long period of time, a small amount of the DMT begins oxidizing to DMT N-oxide. This small amount of DMT N-oxide is now also being exposed to environmental conditions for a long period of time, and begins breaking down into it's degradation product, which is either deep orange or red. This would mean that starting with a crystal that contains a trace amount of DMT N-oxide may be one of the factors that leads to a more rapid orange-ing of the spice. This explanation is consistent with observations that have been made on yellow oil.

On the other hand, it's possible that the orange-red degradation product forms independent of the yellow oil; there isn't enough information to draw any hard conclusions (anyone want to run some TLCs of your old orange spice?). But to the people who are smoking it, the more important issue is what it does, not what it's made of. Combing through the scraps of anecdotal reports on the issue, there seems to be a general consensus: As the spice turns orange over time, it begins to be qualitatively "different" in terms of the experience (but not any less potent), then gradually the sample loses potency and becomes qualitatively unpleasant.

Reports of more drastic changes in the appearance and effects of DMT due to exposure to higher temperatures is covered in Section II.5.A.





I.5.B Evaporated Spice

Another very common form of colored spice results from people evaporating their nonpolar solvent instead of freeze-precipitating. The yellow contained in spice that has been extracted with heptane or naphtha and collected by evaporation appears to just be trace impurities, most likely fats from the rootbark. It is reportedly harsher to smoke, but roughly the same potency as white spice. This yellow fraction (presumed to be plant fats and miscellaneous impurities) can be removed from the spice by recrystallization. There doesn't seem to be any indication that this sort of yellow spice has any biologically active chemicals besides DMT.

It appears that there is another form of yellow spice that can be obtained by evaporating off the solvent, depending on the evaporating conditions. People report a much yellower oily product when the solvent is evaporated with a fan, particularly with warmer temperatures. Others have obtained yellow crystals by melting off-white spice in an attempt to do a "solventless recrystallization". Yellow crystals obtained in this fashion are reported to be qualitatively different than plain spice, and more potent. Based on this information, it sounds like these methods are producing DMT which contains the yellow oil fraction I believe to be DMT N-oxide. Delafonze19 has reported happening on a method for reliably converting white DMT to the potent yellow oil (see Delafonze19's Preparation of Yellow Spice Oil.





I.5.C Alternate Solvents

Heptane and naphtha have not always been the solvents of choice in DMT extraction. Some of the older teks recommend ether, or dichloromethane (DCM). Xylene and toluene are also effective extraction solvents for pulling DMT, though we've seen they're less specific and pull other fractions. All have been reported to yield yellow or even orange spice. Considering the differences in the solvents, it will be easiest to consider them seperately.



Xylene and Toluene

Both of these solvents are known to pull a mixture of DMT and "jungle spice" when used on a nonpolar soup that's been exhausted od spice with an aliphatic hydrocarbon. It's therefor reasonable that they could be used as the primary extraction solvent to pull a similar mixture, but containing a great deal more DMT. One experimentor did just that:

SWIM just decided to extract 100g of MHRB with Xylene and evaporate, just to see the difference between that and a naphtha/freezer precip. After collecting 3 Xylene pulls he had about 130ml of PISS YELLOW Xylene. He evapped that to leave the same circular patterned yellow spikey crystals as the picture.

Editors Note: This refers to the picture on the left in Figure 4.

Oh... my... god! SWIM just finally sampled this batch and for the first time in almost 1 year... the REAL DEAL. He has been searching and searching for this...

SWIM tried just about EVERY known vendor of MHRB and it was all the same... NOT what DMT should be like. So he emailed an obscure, little known vendor asking for a sample. The vendor sent 100g. Well, he finally got a chance to extract and, holy shit, is he satisfied. Entities, geometry, self-transforming machine-flowers. Blown away.

He will always extract the same way from now on... pull with Xylene and evap all the way down, wash with ammonia, and blast off.


Although we can't rule out the possibility that there may have been something idiosyncratic to the bark going on here, this report carries a strong recommendation for using xylene as an alternate extraction solvent if you're looking for some orange spice that apparently has something that the white spice lacks.



Ether

There have periodically been reports of using ether, or a binary solvent of ether/heptane (mostly ether), as an extraction solvent. This invariably leads to a product with yellow discoloration. Since the ether is evaporated to yield spice, it's not necessarily surprising that the product is yellow; we might expect some of the plant fats or other impurities to extract into the ether. On the other hand, ether/heptane (8:1) is known to extract a brown waxy compound as well as DMT, so it's quite possible that some of the yellow color in ether extracts is one of the "jungle spice" compounds. Based on reports of ether extracts smelling "strongly floral", it's also very possible that the ether is extracting some skatole (see GC/MS Analysis).



Dichloromethane

This solvent is recommended by some of the older teks. Recent literature suggests that using DCM as a defatting solvent most likely allows for the formation of N-chloromethyltryptamine, a chemical of unknown pharmacology. It is unknown whether this compound might form when using DCM as an extraction solvent. Orange crystals that result from the use of DCM could have their for the same reason as the orange crystals extracted by xylene. As always, there's also the possibility that the coloration results from a pigment pulled by the DCM. But it's also possible that spice extracted with DCM could contain some quantity of N-chloromethyltryptamine. According to a 2008 publication, "DMT was found to be reactive towards dichloromethane, either during work-up or long term storage therein, which led to the formation of the quaternary ammonium salt N-chloromethyl-DMT chloride" (Brandt et al). I was unable to turn up any reports on the qualitative effects of orange spice extracted with DCM.





I.5.D Odds and Ends

One last possible source of orange DMT could be the use of plant materials other than Mimosa root bark. For example many species of Acacia can yield an orange spice. While some of this color could indeed be plant fats, Acacias have been shown to have a richly diverse chemistry, so it seems entirely possible that some of this color could potentially come from an alkaloid fraction in the bark.

A few other comments on colored spices: I have seen two unrelated references to a "purple spice". One of these was accompanied by a blurry photograph which showed spice which was unmistakeably purple. I cannot concieve of this coloration having come from any of the compounds discussed above. Until some experiences come in with this material, I'd say it's probably best to recrystallize any such material you happen to run across.

I have also seen infequent references to "green spice". This is a mystery that I think I can put solidly to rest. It is only known to have been isolated by evaporating the solvent to collect the spice; further, it's only been reported in cases where the extractor used unsavory brands of naphtha (like Sunnyside). In at least one of these circumstances, the extractor evaporated a clean sample of their nonpolar solvent and discovered that it left a blue residue. Thus it appears that the green spice comes from yellow spice plus an blue non-volatile solvent-additive: yellow + blue = green. Long story short: avoid "green spice" like the plague.

#12 Entropymancer

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Posted 29 March 2008 - 05:31 PM

IV. The Hard Data

Periodically attempts have been made to shed light on the nature of jungle spice by use of GC/MS or TLC. While the evidence is very limited at this point, preliminary data substantiates the idea that some people are isolating DMT oxide, and possibly a degradation product of yuremamine.


IV.1 GCMS Analysis

Posted ImagePosted Image
Figure X. MS of DMT reference standard (left) and Brazilian M hostilis A/B extracted at pH 1 (right)
(from Mambo Pachano's Entheogen Review Article - See Trout's Notes)


Let's first consider the case of a "clean" extraction. In the Entheogen Review, Mambo Pachano developed an "extreme condition hostilis extraction" and had GC/MS analysis performed on the resulting product alongside a DMT reference standard (see Figure X). The acidic extraction was perform with aqueous ethanol acidified to pH 1 with citric acid. The extract was evaporated, taken up in warm water, and defatted with xylene (presumably removing the jungle spice). The water was basified to pH 14 with hydroxide, extracted with toluene and the spice recovered by evaporation. "This has reliably produced a yellow waxy-crystalline massive solid that crushed to white powder."

The DMT reference standard is very clean. There's an abundant molecular ion at 189.1 m/z, and a less abundant peak at 144.1 m/z indicating the loss of the dimethylamine moiety. I'm curious what the trace just above 400 m/z is since the same trace appears on the analysis of the extracted sample, but it's likely of no particular consequence.

The extracted sample also appears to be fairly clean. Extrememly clean when we consider that it was obtained by evaporation instead of freeze-precipitation or recrystallization, and using toluene, which is known to be less selective than the usual alkane solvents. There is a small impurity (abundance ~2) at 205.1 m/z, which is most likely accounted for by DMT N-oxide. This helps to substantiate the idea that the yellow oil is DMT N-oxide, since the product was collected by evaporation, and was described as "a yellow waxy-crystalline" material.



Next we’ll consider a crude extract of the “jungle” alkaloids. This analysis was communicated by Radio879 from the Nook. In his own words, "I think this was the one where I did use xylene instead of naphtha, but I did not wash it with naphtha... In that sample it looks like there's 86% DMT, then 4 other unknown compounds." See Figure X. There actually only appear to be three unidentified compounds in this spectrum. I assume that the "fourth compound" is the peak at 144.1 m/z, which actually comes from DMT (see above note on the reference standard). For all three of the unidentified peaks, I believe I can propose some reasonable assignments.

Posted Image
Figure X. Radio879's GCMS of an unpurified xylene pull, extraction process unknown.



130.1 m/z

This peak had me mystified for the longest time. Too small to be a tryptamine; barely large enough enough to be an indole. But in reading through Trout's Notes A5, I saw that one of the biggest issues they were concerned with in the extraction process was trying to eliminate an alkaloid called "skatole" (see Figure X).

Alkali solutions of pH 14 will destroy skatole (the strong smelling compound that many people mistakenly think is the smell of DMT - the more pure DMT is the less smell it has.


Posted Image
Figure X. Skatole: 3-methylindole


Skatole, whose chemical name is 3-methylindole, is a white crystalline compound which turns brown over time, and has been described as "mildly toxic". It has been shown to cause pulmonary edema in some lower mammals, apparently targetting Clara cells, which are the major site of cytochrome P450 enzymes in the lungs. These enzymes convert skatole to a reactive intermediate, 3-methyleneindolenine, which damages cells by forming protein adducts (Miller et al). It is also added to cigarettes as a flavoring agent.

I have been unable to find any source that explicitly verifies skatole as a known compound in M hostilis, but it certainly seems conceivable. It could explain why people sometimes get a material that looks like spice and smells like spice, but lacks the effects of DMT when smoked. Regardless, the 130.1 m/z molecular ion corresponds perfectly with a methylated indole; This issue requires further analysis to confirm the identification, but it seems entirely plausable. Especially if Pachano can share his source that identifies skatole as a component of M hostilis, I am satisfied with the identification of this peak as a methylindole.


205.1 m/z

This is the same peak that was seen as a trace component of the "clean" extract's GC/MS. Being exactly 16 m/z higher than DMT's molecular ion immediately suggests that this could be an oxide of DMT (the most reasonable place being at the tertiary amine). Since the sample was obtained by evaporation and not cleaned with alkanes, we would expect some of the yellow oxidation product to be present. The issue requires further study be put cleanly to rest, specifically someone running GC/MS and NMR on the purified yellow oil. Until then, I am fairly comfortable with the assignment of this peak as DMT N-oxide.

Posted Image
Figure X. DMT N-Oxide


DMT N-oxide and DMT have been shown to enzymatically interconvert in lower mammals.


350.1 m/z

This one is a doozy, and is the primary evidence in suggesting that what people have been isolating may be a breakdown product of yuremamine. The peak is substantial, less abundant than the proposed methylindole, but more abundant than the DMT oxide. It's substantially heavier than DMT, but also very substantially lighter than yuremamine. And besides, it doesn't hardly seem possible that yuremamine would survive the extraction process.

But I got to thinking: When the yuremamine is degraded during the extraction, it's not as though it just disappears. And unless it loses the ethylamine moiety, the breakdown product still ought to be amenable to acid/base extraction. Some quick calculations indicated that the loss of either hydroxylated phenyl group could get the molecular mass in the ballpark of 350 m/z. And there's that handy hydroxyl adjascent to each of them that could participate in the degradation chemistry. In the end, I came up with two plausible degradation products which would give rise to a molecular ion at 350.1 m/z. Unfortunately, the peak is not abundant enough to analyze its fragmentation pattern.

Posted ImagePosted Image
Figure X. A couple proposed breakdown products of yuremamine, both would have molecular ion at 350.1 m/z

Posted Image
Figure X. Yuremamine


It's also worthwhile at this point to discuss what we would expect to see if the jungle spice were in fact yuremamine. Yuremamine has a molecular ion at 477.1 m/z. This peak has been clearly absent from every attempt to analyze the jungle spice. It also was not seen in any of the analytical work on M hostilis root bark or jurema wine that was conducted during the 20th century. This has led to the speculation that yuremamine is subject to degradation under most extraction conditions, particularly under high temperatures or alkaline environments. Below is the LC/MS spectrum obtained by Vepsäläinen et al.

Posted Image
Figure X.GCMS of Yuremamine (from Isolation and Characterization of Yuremamine)




Finally, we have a more recent report of GC/MS analysis run on the red spice by an acquaintance of Burnt:

Some guy I don't know well told me he can run GC-MS on this compound. He believes he has some of this so-called jungle spice. It is a red crystalline thing that was originally oozy. After recrystallizing white crystals out of it he saved this other stuff. He believes if his bad memory serves him right that it came from toluene or diethyl ether pull from an acid base extraction. He was wondering what it could have been.

GC-FID and GC-MS main compound = spice (nothing else in GC-MS) (minor minor peaks in GC-FID). It is curious because yea the whole reason this guy has some of this stuff is because it was not soluble in the hexane.


This is a confounding result. The material was a red crystalline material isolated based on its insolubility in hexane, which certainly sounds like jungle spice. We would expect very little of the material would be DMT due to the hexane wash, but it was still the primary peak in the sample.

There are a handful of possibilities, most of which Burnt himself pointed out. It's possible that the material analyzed was not the same material that others are calling jungle spice; this seems unlikely since it matches the same physical description and was isolated in the same fashion. The material was also reportedly stored for several months prior to analysis, so it's possible that the compound(s) of interest degraded during that time. Or for whatever reason, the red component may not be amenable to GC/MS; this in itself would be strange for a chemical that is reported to be biologically active when vaporized.

There are two other possibilities, if we take the spectra at face value and assume that DMT is overwhelmingly the main component in the red spice. The first of these possibilities is that the red coloration comes from a biologically inactive tannin, and the activity of the red spice is solely the result of DMT. I don't consider this possibility to be very likely, based on the wealth of experience reports reporting breakthroughs on significantly smaller doses than DMT could provide.

The other possiblity, assuming that DMT is overwhelmingly the main component in the red spice (which I'm not necessarily convinced of), is that the trace impurity responsible for the red discoloration is biologically active and accounts for the reported effects of smoking red "jungle spice". If this is the case, it could either be acting as an agonist in its own right, and adding its effects to the effects of the DMT, or it could be potentiating the DMT in some fashion. Since no trace components were identified in this particular analysis, it is impossible to speculate further.





IV.2 TLC Analysis



I did some tests (TLC) recently that showed at least 3 compounds in a MHRB extraction. 1) is DMT 2) is 5MeODMT and I *suspect* 3) to be either DMT Oxide or 5MeODMT Oxide. I need to run some further test to be sure of #3. None of the spots showed up as what I would consider trace amounts. The main point here is that what is being extracted IS most likley a mixture.

Edit by Dozuki: It is NOT 5MeO.

Well, I was waiting till I came up with an explaination for some other findings on this, and aquired a reference sample for 5MeO before I posted any more. Further TLC runs on this same extract failed to show the blue spots (after 4 days). This is NOT 5MeO DMT as I thought that it was. The compound on the plate is unstable and dissappears. A recent post on the Ayahuasca forum leads me to believe that this is Yuremamine and not 5MeO. In the above solvent system it shows the same Rf and color reation to Xanthydrol as 5MeO. Attached is the first plate showing what I now believe to be Yumamine (see Figure X)

(What solvent did you use for the extraction?)

The standard 'net' A/B extraction for the first lane, and Toluene for the 3rd lane. I'm interested in the red/pink/purple coloration that is common to many tryptamine bearing plants. It comes from tannins (lots in this case) and I also believe an oxidised tryptamine. Its the oxidised compounds that are tricky...

I ran some other tests on this same extraction (after the blue spot no longer showed up). I used a different developer for the plates (that resolves 5MeO/Dmt better). No blue spot (as expected), but the one trace in the original plate remains. I ran this against on oxidised sample of the initial extraction, and the trace is not Dmt - Oxide (shows as a very different Rf), its yet another trace compound. Not sure what yet. The oxidised sample, when left to evaporate yeilded a yellow oil that smells very floral. It did not want to crystalize.


Posted Image
Figure X. Dozuki's TLC plate analyzing normal acid/base extracts and fractions extracted with toluene



A few days later, he's run some further extractions and plates, and posted the following:

Here's the preliminary highlights from this weekends Thin Layers:

Trying to get to the bottom of what is in the extractions of MHRB and where the yuremamine is in these extraction was the main goal. A review of the tannins thread (in a nutshell) shows that yuremamine shows up in an MeOH extraction and that it seems not to show up in a stardard A/B extraction. That Yuremamine is decomposed under alkali conditions and these decomposition products are likley to be the ubiquitous 'Jungle DMT' or what I will refer to as YDP (Yuremamine Degradation Product). Published bio-assays (The Entheogen Review) indicate that MHRB as a cold H2O extraction are orally active, and yuremamine is the suspect for the oral activity.

For the samples: 2 gms MHRB (ground) was extracted for 1 hour in 10ml H2O. This was done twice and the extractions combined. Another 2 gms MHRB (ground) was extracted for 1 hour in 10 ml MeOH. This was done twice and the extractions combined. Both were done at room temperature. These extractions were spotted directly on the plates. The first lane was the control. This was a standard A/B extraction done earlier (Same sample as in the 'DMT Melted' thread). Visualization was done with the bare plate, and xantydrol.

Plate #14 is run in an acid environment, so as not to degrade the yuremamine. Lane 1 is the control showing Dmt (rF @ B) and a YDP (rF @ A). Lane 2 is the H2O extract and Lane 3 is the MeOH extract both showing Dmt (B) and very likley yuremamine ©. Lanes 4 and 5 are lanes 2 & 3 before Visualization with xanthydrol. What's interesting here is that the pre-viz lanes show the C spots as blue and the spots as purple after visualization. The YDP soes not show up in lanes 2-5 (the pencil lines on the right just indicate *ALL* rF positions).

Plate #12 is run in an alkali environment. The layout of lanes 1-3 remains the same, but we see a reversal of yuremamine and the YDP rF values in relation to Dmt. However, since this is run in an alkali environment, we see the YDP showing up in lanes 2 and 3 as the spots travel up the plate and degrade the yuremamine which now only shows as a smaller trace component. By the time the plate was fully developed the blue spots on the plate before visualization had dissappeared. They remained for about 1/2 of the run and then were gone by the time the plate finished.

So, Plate #18 is the reference in lane 1, the visualized MeOH extraction in lane 2 and the pre-visualized MeOH extraction in lane 3 run in an alkali environment for 1/2 of the plate (1/2 the distance to reduce the time spent in the alkali environment). Here A is Dmt, B is the YDP, C is yuremamine, D and E I believe are yuremamine being broken down and have not had a chance to settle into a true rF value as the plate run has been shortened. Edit note: The blue E spot in lane 3 is a tannin.

So, conclusion are thus: The both MeOH and H2O at room temperature will extract *BOTH* Dmt and Yuremamine, and that a trace component found in standard A/B extractions is a YDP. Yuremamine is visible on the plate without a visualization agent Edit note: now unsure of this statement , and I suspect that it flouresces (will have to get a black light). That the oral activity of a cold water extraction could very well be that yuremamine is acting as an MAOI making the Dmt orally active (since it's being extracted) and it could well be active in and of itself. Also, H2O will extract Dmt, MeOH seems to be a little more efficient. And lastly that the tannins are hard to deal with and it would make reading the plates easier without them (they are the red streaking).


Posted ImagePosted ImagePosted Image
Figure X. Dozuki's TLC plates, #14, #12, and #18 (from left to right)


And some further comments:

I ran about 10 plates with these particular extractions (H2O&MeOH) in 6 different eluent systems as well as one 2 dimensional plate. Plate #14 is run in: IPA:AcOH:H2O (9:1:1 - 91%:30%:100%) All easily aquired solvents. Plates #14 and #18 are in IPA:NH4OH:H2O (9:1:1 - 91%:10%:100%). The streaking is tannins, not all of the tannins, but a vast majority of them. And yes, it's overloaded. At about 29% of the makeup of the original material it's a little hard not to overload the tannins if you want the other cmpds to show up. The samples are spotted at ~ 2-3 micro liters. Doing less than this and you miss some of the other compounds that are present (its possible to miss some even at this low of an aliquot). I have ran some plates on this same extraction with most of the tannins removed at an aliquot of 10 - 12 micro liters and more compounds become visable (will post these at a later time). The reference sample is from a standard A/B extraction of MHRB using naptha as the NPS. The plates are Silica GF @ 200 microns (Analtech plates).

As for Ehlirch's, I didn't really find that the color was good for determination between the genotypes (G,M,T) of phalaris, with spots showing basicly the same color (purplish blue) for all three. Xanthydrol is a better colorametric agent according to the literature (pink-G,blue-M,purple-T). Also, 5MeO and Dmt generally show the same rF with n-Butyl:AcOH:H2O, and the IPA:NH4OH:H2O is supposed to resolve these 2 cmpds alot better according to the lit. I havn't gotten far enough away from MHRB yet to find out if this is so, but so far I'm impressed with this system (tight spots, wide seperations). The ratios can be tweaked as well so that the NH4OH doesn't degrade the yuremamine as quickly, alowing longer runs (more acurate rFs), but there is a little less seperation.



#13 Entropymancer

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Posted 29 March 2008 - 05:32 PM

V. Botanical Confustication

I'll say right off the bat that this section is less than satisfactory in terms of drawing any concrete conclusions. None of the vendors I contacted had any idea what color flowers were produced by the trees our rootbark comes from, though some said they'd send the question down the line. At the very least, I can outline the various issues that seem to be confusing the issue.





V.1 Hostilis? Tenuiflora? Verrucosa?!?!

The very first issue that I'm not satisfied with is the extent to which Mimosa hostilis and Mimosa tenuiflora are identical. It's certainly well established in the literature that these latin binomials are synonymous. There is no doubt that M hostilis and M tenuiflora are both legitimate names to apply to the white-flowering tree from which the bark is theoretically being harvested. On the other hand, there are some indications that

In Mexico, following some catastrophic events in the '80s, the tannins in M tenuiflora rootbark, called "tepescohuite", have been hailed as a miracle-treatment for burns when applied as a topical ointment. This seems to have given rise to a proliferation of tepescohuite throughout southern Mexico, and it seems likely that sources distributing Mexican root bark are probably distributing bark from the tepescohuite. The problem is, I'm not convinced that all of this tepescohuite is actually M tenuiflora.

There are several vendors peddling Mimosa tannin-based ointment who seem to indicate that their Mimosa has a bright yellow flower, though it's still claimed to be Mimosa tenuiflora. Less frequently, there are vendors distributing similar preparations who identify their Mimosa as having a bright pink flower. It seems reasonable that, since there was such a high demand for the ointment, and several Mimosa species have similar rootbarks, someone may have unknowingly or unscrupulously begun propagating another species as tepescohuite. The possibility of this misidentification might be of interest to any supplier obtaining their product from Mexico. On the other hand, I've seen some popular speculation that the Mexican rotbark has a higher alkaloid content, so the possibility of a misindentification doesn't necessarily mean an inferior product for extracting purposes.

Posted ImagePosted Image
Figure X. Images associated with Mexican tepescohuite


Also casting doubt on the identity of the rootbark are the seeds. Consider what Torsten of Shaman Australis had to say:

Mimosa species can contain some nasty alkaloids, which is why correct identification is paramount in my opinion. That is why I am so appalled at the callous nature of MHRB farmers, distributors and retailers. I am also a little surprised at the ignorance of the customers. I mean seriously, you folks seem to only care about the fact that a plant contains DMT regardless of what else you might consume along with it.

So is there a conspiracy to supply dodgy material? I don't know. All I know is that two of the largest MHRB farmers also supply seed from their plantations to various wholesalers and retailers. I have purchased plenty of this seed for my own shop and have bought seed from most major retailers. NONE of it has turned out to be M.hostilis.


The seeds which have been distributed as M hostilis seem to almost invariably produce plants that are of the genus Mimosa, but are definitely not M tenuiflora. I have yet to find a verified report of any vendor selling "M hostilis seeds" that actually give rise to an M hostilis tree. Most of the "M hostilis seeds" available these days appear to produce Mimosa verrucosa trees, including the seeds from BouncingBearBotanicals and Shaman Palace.

Mimosa verrucosa is the "Jurema branca" used by some indigenous South American populations (in contrast to "Jurema preta", which is our old friend M tenuiflora). However, it appears that nomenclature varies among indigenous populations in South America, which may be causing misidentification by miscommunication. Consider the following quote from a 1998 MAPS Newsletter

After interviewing many people, and participating in different Jurema rituals with the Indians, I also realized that the Jurema they drink in their brew is not Mimosa hostilis, but the root bark from Mimosa verucosa. Different tribes will call M. hostilis, the Jurema Negra and M. verucosa, the Jurema Branca, as well as other tribes call M. verucosa, the Jurema Negra. That means that when they say that they drink Jurema Negra, it does not necessarily mean they are drinking M. hostilis, but M. verucosa which is called both: Jurema Branca and Jurema Negra.


In years past, there were misidentified seeds that produced Mimosa pudica or even Mimosa scabrella, but these appear to have faded from the marketplace. Sometimes genuine seeds have been acquired through trades with people in possession of genuine specimens. Live cuttings of genuine specimens are also sometimes traded amongst the ethnobotanical community.

The scarcity of genuine seeds and the concurrent abundance of misidentified samples begs the question: Have the imported root bark samples been similarly misidentified? After all, it doesn't make much sense that a vendor would be able to acquire legitimate Mimosa tenuiflora rootbark, but unable to acquire legitimate seeds from the same source. On top of this, Torsten of Shaman Australis reports having seen a photo of the Mimosa plantation from which a major vendor obtains it's rootbark, and the flowers on the trees were pink.

Mimosa tenuiflora has white flowers. It does not have pink flowers, or purple flowers, or yellow flowers.

As you can see, this leaves us with a nicely jumbled picture that casts a significant shadow of doubt over the botanical identity of the rootbark that's being imported.





V.2 So what have we been extracting from, and does it matter?

Considering the evidence, I think we can say with a fair degree of confidence that the root bark that everyone has been extracting is Jurema. The question is whether it's Jurema preta (M hostilis) or Jurema branca (M verrucosa). I have a hard time imagining that 100% of the vendors have been sold the "wrong" species of Jurema, so I'd wager that at least some vendors are probably selling legitimate M hostilis root bark. Considering the scarcity of genuine seeds, I'd be hesitant to speculate that genuine M hostilis root bark is prevalent on the market. That said, it seems exceedingly likely that some of the root bark available online is in fact M verrucosa. Unfortunately, unless vendors can find out what color flowers their suppliers' trees produce, it is impossible to speculate on the degree to which M verrucosa is being sold as M hostilis.

This brings us to the second question, does it really matter? Despite all of the indications that some of the bark may not be from M hostilis, I haven't heard any confirmed reports of bunk batches of bark being sold. We're all familiar with the periodic reports of low-yielding bark from various vendors, but these samples still seem to contain N,N-DMT in significant concentrations (>0.2%). I vaguely recall an unsubstantiated report of a person extracting a white crystalline solid that looks like spice, but was completely lacking in physiological activity; this could indicate that the rootbark used was from another species, but without multiple consistent reports, I can't lend it too much significance.

So for those who are concerned solely with extracting the N,N-DMT, the answer is: No, it doesn't really matter whether the rootbark you've been buying is actually M tenuiflora. Whatever it is, it serves as an effective source of DMT, with minimal fat content to contaminate the extraction product. There has been some speculation about the possible dangers of a misidentified rootbark, and the most frequent concern is that the unknown bark may contain mimosine, a toxic clastogen (chromosome-breaking chemical).

Mimosine has been isolated from M pudica, as well as a few other species. According to K Trout, no studies have been done to establish the chemical makeup of M verrucosa root bark, so it is impossible to speculate one way or the other about whether mimosine may be present in popularly extracted rootbark. If we want to assume for safety's sake that it is present in the bark, it appears easy to make certain it doesn't end up in the final product. Mimosine is much more polar than DMT, and is practically insoluble in higher alcohols, ether, benzene, chloroform, etc. This means that very little mimosine is apt to end up in the nonpolar pulls when you extract the DMT freebase. Since mimosine is substantially more soluble in water than in nonpolar solvents, the sodium carbonate wash (as described in Vovin's tek) ought to remove any residual mimosine.

So that's all well and good for the average spice extractor, but what about the folks pulling jungle spice? It is certainly tempting to claim that some of the variability among different jungle spice extractions can be accounted for as the result of different species of mimosa being sold as the same product. Unfortunately, such a claim would be completely indefensible. The truth is, we don't know how much of the root bark on the market comes from which species. It's entirely possible that misidentified rootbark is a significant factor in jungle spice extraction, but until someone runs extractions of jungle spice on confirmed samples of M tenuiflora and M verrucosa, we just don't know.

There is also the possibility that a large amount of the variation in the jungle spice may be accounted for by differences in environment or harvesting conditions. Maybe the tree needs ample access to a particular nutrient in the soil to produce a good portion of jungle spice. Maybe the quantity of this alkaloid fraction varies with the time of year, or even with the time of day. Maybe the tree must reach a certain age before it begins producing it. Or a million other things. Or maybe all of the variability has to do with unrecognized nuances in the extraction process. As I said, this section is far from satisfying, and leaves open a lot of loose ends, but that's how it stands today.

It is also worth mentioning that this confusion over the botanical identity of the avaiable rootbark may explain why a few people have been unsuccessful in attempting to verify Jonathan Ott's claims that jurema is orally active without an added MAOI. The individuals who were unsuccessful may have been using M verrucosa while Ott was using M tenuiflora.

#14 Entropymancer

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Posted 29 March 2008 - 05:34 PM

Just a little more jungle spice information for y'all to sink your teeth into :hippie:

#15 tregar

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Posted 01 April 2008 - 02:32 PM

Excellent article & work, thanks Entropymancer.

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Posted 01 April 2008 - 09:18 PM

excellent thread! your work is greatly appreciated and more info such as this,
and/or more copy-overs from the nexus or elsewhere are encouraged :)
thanks again for takin the time, friend :bow:

here are some alleged M. hostilis seeds --
http://mycotopia.net...=1&d=1207102533
note the varying sizes and colors

for what its worth, the seeds of the common 'mimosa tree' ,
tend to be way more uniform in size and shape, as well as consistantly dark, almost reddish brown and not quite as glossy-lookin,
but still do carry a bit of a semi-gloss-kind-of sheen to them.
when i find a camera i will post pics of these 'bunk' mimosa seeds for identification help :)

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#17 Omnis Vorum Dux FFF

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Posted 04 April 2008 - 02:20 AM

excellent stuff SWIM is building a column just to shed some more light on this SWIM will also be recording exp reports :reb:

#18 Entropymancer

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Posted 28 June 2008 - 01:07 PM

Bump! I've finally finished editting and revising the article to my satifaction. All claims are now thoroughly cited, and I believe it's an accurate reflection of everything that's currently known about these alkaloids.

Now in printable pdf form (36 pages), I present the finalized version of Jungle Spice: Mystery Alkaloids of Mimosa Root Bark.

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#19 extrememetal43

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Posted 28 June 2008 - 08:31 PM

this is the best damn collection of info on everything dmt and every other alkoloid we pull outa this stuff. Dude, i remember reading it months ago and read it again the other day...amazing stuff...nice work man :bow:

#20 KingKanibalKiller

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Posted 28 June 2008 - 09:28 PM

excellent




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