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"Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark

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Entropymancer said:
"Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark

by Entropymancer​

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


So just what is Jungle spice?

Jungle spice is one of many names that have been applied to an intriguing non-DMT alkaloid fraction that can be isolated from much of the commercially available Mimosa root bark (See V. Botanical Confustication).10,11,17 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 N,N-DMT in addition to the more mysterious alkaloids; 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.15,19 Which compounds are actually isolated depends on some several of the following factors: the source and botanical identity of the root bark, the conditions of cultivation/harvest, and various pH, temperature, and airflow considerations throughout the extraction process.10,11,24,26 About all that is certain about it at this point is that it contains some psychoactive material that 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 2005.8,20,24 Looking at the evidence, this scenario appears exceedingly unlikely based on yuremamine's known instability to base and speculated instability to heat.8,24 It can't yet be ruled out completely, but there remains a substantial body of evidence against this identification. Until an LC-MS 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, and clear the way for future investigators to finish unraveling this mystery.



Table of Contents
I. Diversity of the Extracted Compounds
- I.1 Red/Brown Crystalline Goos
- I.2 Tan Waxes
- I.3 "Kokusaginine"
- I.4 Yellow Oils
- I.5 General Comments on "Colored Spice"
- - I.5.A Old Spice
- - I.5.B Other Considerations, Botanical and Synthetic
- - I.5.C Evaporated Spice
- - I.5.D Alternate Solvents
- - I.5.E Odds and Ends
II. Experiences
- II.1 Experiences Smoking the Red Crystalline Goo
- II.2 Experiences Smoking Tan Waxes
- II.3 Experiences Smoking Colored DMT
- II.4 Reports of Oral Activity
- II.5 Reports of Changes in Alkaloid Activity with Age and Heat
- - II.5.A Experiences with Old Spice
III. Isolation Techniques
- III.1 Entheogenist's Jungle Tek
- III.2 Critical Switch's Tek
- III.3 Isolation of "Kokusaginine"
- III.4 Delafonze19's Preparation of Yellow Spice Oil
- III.5 Alternate "Dark Spice" Isolation
IV. The Hard Data
- IV.1 Mass Spectrometry Analysis
- IV.2 TLC Analysis
V. Botanical Confustication
- V.1 Hostilis? Tenuiflora? Verrucosa?!?!
- V.2 So what have people been extracting from, and does it matter?





I. Diversity of the Extracted Compounds

Probably the biggest issue complicating the mystery of jungle spice is the sheer diversity of compounds that can be extracted using apparently identical methods.14,15,17,19,22,24,26,30 Based on their physical properties, we can classify three distinct types of material that can come from the xylene/toluene pull. Considering the reported pharmacological activity of these materials in human subjects, the picture becomes much more complicated.



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."
Entheogenist14

"Could you describe the material? My friend's has the consistency of a soft crayon and is brick red."
Noman14

"The junglespice I got is just like a piece 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."
QuantumBrujo14

"Swim succeeded in pulling the red spice. It's a dark , deep crimson color , almost the color of dried blood."
Spicemeister17​


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, in some cases washing the dark gunk with naphtha leaves behind a red solid which is insoluble in the naphtha (Figure 1). This red material has been isolated both by straight-to-base extraction and by acid/base extraction.14,19,22,24,26,33

The crude extract is invariably an impure mixture. In most cases, pulling the alkaline aqueous phase with xylene extracts a bright yellow color into the solvent; the red pigment isn't seen until the solvent is evaporated.24,28 When the DMT and other impurities are removed from the crude extract by a warm wash in an aliphatic hydrocarbon (naphtha, heptane, etc.), several extractors report that the recovered DMT crystals remain stained yellow.17,24 This yellow fraction of the jungle spice that's soluble in warm naphtha could be several different things (see I.4 Yellow Oils).

It is important to note that some people obtain an explicitly brown goo from the xylene pull, with no indication of red coloration whatsoever (Figure 2).24,17,22,24 Although they may appear similar to the crude red/brown goo on initial inspection, exclusively brown extracts appear to yield a different product, distinct from the red material (see I.2 Tan Waxes). 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.24

Of course, we can't rule out the possibility that the red material may be a mixture of multiple alkaloids. For example, it seems plausible that the red material might have essentially the same chemical composition as the tan waxes, with the addition of a small amount of a red pigment that's responsible for the differences in appearance (color and consistency) between the red material and the tan waxes.


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."
Archaea17

"[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."
Noman24​


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 vary widely from extraction to extraction.33 It is obtained exactly the same way as the red material above; an aqueous hydroxide solution containing mimosa alkaloids is extracted with several 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 the crude jungle spice. Washing this crude material with hot naphtha yields a waxy solid, ranging in color from tan to orange to brown.24,15,22,17

This material has been isolated from both acid/base and straight-to-base procedures.24,17,33 Its isolation has also sometimes been positively correlated with heating the naphtha pulls prior to the aromatic pull, but unless further evidence corroborates it, this will be considered to be coincidental.24 Again, we'll run into some further confusion when we look at the reported pharmacological activity of this material, indicating that there may be more than one compound here. Specifically, this is the fraction of jungle spice which is most frequently reported to change activity over time, indicating that some chemical reaction (presumably oxidation) is occurring.25,15,13



I.3 "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 activity.9,17,24,31 Generally these posters cite the 1999 Entheogen Review article where Jonathan Ott and K. Trout are asked their opinions on the matter.6 Unfortunately, these people seem to have read no further than the second paragraph before leaping to this completely unfounded conclusion. To summarize:

The article begins with a question from a reader, "J.S, OR".


K. Trout was asked about this, to which he replied


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


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 appear to substantiate the latter explanation.8 Regardless, I hope that this can put to rest the idea that the soporific component that has been isolated from Mimosa root bark is kokusaginine.

Based on physical descriptions as well as reports of its effects, it appears that the compound that people have typically been calling kokusaginine is identical with the tan waxy material, and is usually described as being very hard.17,24 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.11,13,17,24,26 (For an account of the isolation of this fraction, see III.3 Isolation of "Kokusaginine")



I.4 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 Member26

"It's yellowish. Even a yellow crystal. Smells the same as DMT with a musty overtone."
Heyoka16

"After two recrystallizations on the N,N- that came out with [the jungle spice], swim tells me it is irretrievably stained yellow and resembles egg yolk."
Spicemeister17​


This is by far the most ambiguous 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.9,12,16,24 When spice is extracted with xylene/toluene or diethyl ether (without using naphtha first), it also tends to come out with a bright yellow-orange discoloration.13,15,17,24,28 The most substantial evidence that there is more than one compound in the yellow oil is the ambiguous solubility of the material. Yellow oil is separated from jungle spice based on its solubility in naphtha, while at the same time a yellow oil can be removed from DMT (extracted by standard straight-to-base methods) based on it's insolubility in hot naphtha. Clearly these must be different yellow oils.

To further complicate the issue, it's very difficult to isolate the yellow oil on its own. 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.9,16,24 These yellow crystals are sometimes reported to be qualitatively better in terms of effects than pure DMT.16,28,32 Also, when washing the crude jungle spice extract with warm naphtha, some extractors report that any N,N-DMT they recover from this process is strongly yellow-colored, and that this pigment seems impossible to remove by typical purification methods. Unfortunately I haven't been able to find any experience reports specifically using such yellow-stained DMT.17,24

Investigating the possibility of the yellow oil being DMT N-Oxide, I found a 2005 paper reporting the isolation of this compound 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.3 This is only useful in that someone with access to proton NMR spectroscopy who obtains a sample of yellow "oxidized" DMT could use this information to conclusively establish the identity of this material. One home extractor who did some TLC analysis on whole and purified extracts of Mimosa root bark described DMT N-oxide as a yellow oil, though I can't corroborate this decription in the published literature.12 On a related note, one home extractor has discovered a method for reliably converting bright white spice into a yellow oil (without using any synthetic reagents); the nature of the process indicates that the yellow oil it isolates is in fact an oxidized derivative of DMT (see III.4 Delafonze19's Preparation of Yellow Spice Oil).32

Looking at the Radio879's LC-MS 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 side-product of the extraction process.19 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.8 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 root bark (see V. Botanical Confustication)19,29



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."24

"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."24

"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."24​

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.11,13,16,17,24,27,28 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 the 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 definitely 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 Bong15​

Probably the simplest form of colored DMT comes from samples that were originally pure white spice. As the samples age, they turn orange and waxy over time.16,18 There seems to be substantial disagreement over the amount of time necessary for this process to occur.16 Some people report a change in color become noticeable after several weeks to a month, while others have samples that are over a year old and still without discoloration.16,18 One potential determining factor is the amount and type of impurities present in the sample. This is corroborated by differences in the DMT's shelf-life positively correlating with differences in the clean-up process used to extract it; multiple samles which turned color rapidly with age had not been washed with ammonia or bicarbonate, while the year-old sample had.16 This would tend to indicate that either residual hydroxide from the extraction, or perhaps some trace phytochemical that the alkaline polar wash removes, is responsible for the change in the DMT as it ages. Anecdotal evidence indicates that higher temperatures speed this degradation process.13,18 It is unknown whether environmental factors such as air moisture may play a role in the rate of degradation.

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 an oxidation product of little consequence. 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 its 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 will lead to a more rapid orange-ing of the spice. This explanation is consistent with observations that have been made on yellow oil, but at present remains entirely speculation.

On the other hand, it's very 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 that started out white?). 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.18,24 It has been suggested that the difference between fresh spice and very old spice is like the difference between fresh spice, and the residue that can be scraped from the inside of the freebase pipe used to smoke it.13

Reports of more drastic changes in the appearance and effects of DMT due to exposure to higher temperatures are covered in II.5.A Experiences with Old Spice.



I.5.B Other Considerations, Botanical and Synthetic

When talking about old spice from back in the '60s, '70s, and '80s, it's important to recall that we're not necessarily talking about the beautiful snowflakes of DMT that any Joe Blow can now extract from M hostilis root bark. It was only in the winter of 1996 that the Entheogen Review reported Mimosa hostilis as "a potent new ayahuasca analog."5 Most extraction processes purveyed on the internet in the early- to mid-'90s were aimed primarily at obtaining a smokable DMT goop. As far as I know, there isn't a lot of clear information on whether the DMT circulating in previous decades was of synthetic origin, or extracted from plant materials. These are important considerations, as the initial purity and the chemical properties of the contaminants are key factors in determining how the material ages. Most of the discussion here assumes that the extraction was done by processes which have been popular among internet extractors.



I.5.C Evaporated Spice

Another very common form of colored spice results from people evaporating their nonpolar solvent instead of freeze-precipitating.9,28 The yellow pigment contained in spice that has been extracted with an aliphatic hydrocarbon and collected by evaporation appears to just be inconsequential trace impurities. Most likely these are fats from the root bark. It is reportedly harsher to smoke, but roughly the same potency as white spice.9,28 This yellow fraction can be removed from the spice by recrystallization.24 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 evaporation conditions. People report a much more yellow oily product when the solvent is evaporated with high airflow from a fan, particularly with warmer temperatures.9,24 Others have obtained yellow crystals by melting off-white spice in an attempt to do a "solvent-less recrystallization".32 Yellow crystals obtained in this fashion are reported to be qualitatively different than plain spice, and slightly more potent.9,28,32 Based on this information, it sounds like these methods are producing DMT which contains the type of yellow oil I suspect to be DMT N-oxide. Delafonze19 has reported happening on a method for reliably converting white DMT to the potent yellow oil (see III.4 Delafonze19's Preparation of Yellow Spice Oil).32



I.5.D 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), or aromatics like xylene and toluene.24,28 It's also entirely conceivable that decades ago, extractors might have used benzene as their nonpolar solvent. All of these are effective extraction solvents for pulling DMT, but as we've seen, they're less specific and pull other fractions. All have been reported to yield yellow or even orange spice.11,17,24,28 It will be easiest to consider each solvent separately.



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 of spice with an aliphatic hydrocarbon.19,24,14 It's therefore reasonable that they could be used as the primary extraction solvent to pull a similar mixture, but containing a great deal more DMT.19,28 One experimenter did just that:



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. Another extractor also obtained an orange material using xylene as the extraction solvent, and had a sample of this analyzed by LC-MS; this has allowed for some discussion of the identity and abundance of the other compounds extracted by this solvent (see IV.1 Mass Spectrometry Analysis).19



Ether

There have periodically been reports of using ether, or a binary solvent of ether/heptane, as an extraction solvent.17,24 This invariably leads to a product with yellow discoloration. Since the ether is evaporated to yield spice, it's not surprising that the product is yellow; we might expect some 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 along with the DMT, so it's possible that the yellow color in ether extracts is a trace amount of that jungle spice fraction. Based on reports of ether extracts smelling "strongly floral", it's also quite possible that the ether is extracting some skatole (see IV.1 GC/MS Analysis). It is curious to note that, while ether, dichloromethane, and aromatic solvents have all been reported to pull jungle spice, ether is the only one of these solvents not reported to produce orange crystals when used alone as an extraction solvent. This is particularly interesting when one considers that ether is also the solvent associated with the hard tan wax some have called "kokusaginine", and has never been reported to extract a red product when used as a solvent to obtain jungle spice.17,24



Dichloromethane

This solvent is recommended by some 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.2,3 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 be colored for the same reason as the orange crystals extracted by xylene. There's also the possibility that the color results from a pigment pulled specifically by the DCM. Finally, there's the possibility 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."2

I was unable to turn up any reports on the qualitative effects of orange spice extracted with DCM. This compound is unlikely to be psychoactive based on its presumed low bioavailability; potential toxicity concerns are unknown. One extractor decided to perform some experiment to establish whether the orange color was extracted from the plant, or whether it might be the rearranged N-chloromethyl- derivative. After obtaining an orange material from a Mimosa root bark extraction with DCM, he tried extracting Chacruna leaves by the exact same process, also using DCM, and found the result in the latter case to be pure white DMT.11 This result strongly indicates that the formation of rearrangement products is not of major concern when using DCM, and the difference in the product using this solvent is a result of its lower selectivity as compared to typical alkane solvents.





I.5.E Odds and Ends

The use of plants other than M hostilis as sources of DMT was alluded to above; this provides another possible source of reported orange DMT. Many species of Acacia, for example, can yield an orange crystalline product on extraction. 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.3,24 Specifically, some of the color might even come from 5-MeO-DMT, which is substantially more potent than DMT by weight. Further, a colleague who recently encountered some bright red DMT inquired and found that it had been extracted from a species of phalaris grass.36

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 unmistakably purple. I cannot conceive of this coloration having come from any of the materials discussed above. Until some experiences come in with this material, I'd say it's probably best to recrystallize any such spice you happen to run across.

I have also seen infrequent 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 a blue non-volatile solvent-additive: yellow + blue = green. Long story short: avoid "green spice" like the plague.




II. Experiences

Below are a collection of experiences that people have had consuming the jungle spice. By and large, the method of administration in the reports was smoking, but there are a few reports of oral consumption of the jungle spice (either by itself or in an attempt to potentiate DMT). The reports do not yet allow us to paint a conclusive picture about the activity of these compounds, mostly owing to the tremendous variability in the extracted material. Where they have their values is in providing the real heart of the evidence that there is an as-yet unidentified psychoactive compound at work here. The sheer volume of reports detailing different or stronger effects at lower dosages than are used with ordinary DMT is overwhelming evidence that there is an unsolved piece in this puzzle.

I've tried to preserve all their original form and content, but I have made a few edits for punctuation, spelling, and grammar.


II.1 Experiences Smoking the Red Crystalline Goo























II.2 Experiences Smoking Tan Waxes











II.3 Experiences Smoking Colored DMT

There don't appear to be any experience reports by folks who've extracted and purified a yellow oil. However, there are some experience reports available with orange or yellow "colored spice", which are discussed in Section I.5.









II.4 Reports of Oral Activity











II.5 Reports of Changes in Alkaloid Activity with Age and Heat

Again it will be convenient to organize these reports by the starting material. Since most or all samples of jungle spice appear to contain some residual DMT, it will be useful to first address changes in activity over time observed in "pure" (white) spice over time. The preliminaries of this issue were discussed above (see Old Spice), so the subsequent discussion will be confined to the drastic change in activity that seems to occur when mild to moderate environmental heat is involved. After that, we'll consider the reports of changing effects over time as they pertain to the jungle spice. No reports could be found on the effects of the red crystalline form of jungle spice changing over time, but the phenomenon was reported several times with the tan wax fraction.11,17,24



II.5.A Experiences with Old Spice













II.5.B Experience with Tan Waxes Over Time








III. Isolation Techniques

None of the following extraction methods are mine. Credit is given where credit is due.


III.1 Entheogenist's Jungle Tek24




III.2 Critical Switch's Tek19

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 primarily for historical relevance.





III.3 Isolation of "Kokusaginine"24

As discussed above, this fraction is almost certainly not kokusaginine, 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, though there is some evidence it may leave behind the red material that aromatic solvents will pull.17,24 The original author is unknown to me; this was cross-posted by Implants.





III.4 Delafonze19's Preparation of Yellow Spice Oil32

After freeze-precipitating the DMT, the naphtha was poured off and the solids allowed to dry in a jar. Hot water is then run over the jar, melting the spice. This process promotes the conversion of the white crystals into a yellow oily crystal which is reportedly more subjectively enjoyable than white spice. If the yellow oily crystals are left out with moderate exposure to air for a week, the process appears to proceed further towards completion, turning the material into a yellow goo.



III.5 Alternate "Dark Spice" Isolation26

The original author is unknown. This was cross-posted by Orbit:







IV. The Hard Data

Attempts have periodically been made to shed light on the nature of jungle spice by use of GC-MS, LC-MS, or TLC.12,13,19,31 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.13,19 The other major conclusion that seems to have come out of these attempts is establishing that no unique chemicals besides DMT can typically be seen in GC-MS analyses, while LC-MS shows a wider range of compounds.8,19,31


IV.1 Mass Spectrometry Analysis


Figure 5. 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 A5)7​

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 5).7 The initial extraction was done 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 any 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."7

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.7

The extracted sample also appears to be fairly clean. Extremely clean when we consider that it was collected 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 could easily be 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.7



Next we consider a crude extract of the “jungle” alkaloids. This analysis was communicated by Radio879 from the Nook.19 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."19 (See Figure 6) 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.


Figure 6. Radio879's LC-MS of an unpurified xylene pull, extracted by an acid/base process.31​


130.1 m/z

This peak had me mystified for the longest time. Too small to be a tryptamine; barely large enough to be an indole. But 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 7).7




Figure 7. 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 targeting 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.4 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 plausible. 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 (Figure 8.). Incidentally, DMT N-oxide and DMT have been shown to enzymatically interconvert in lower mammals.


Figure 8. DMT N-Oxide​



350.1 m/z

This one is a doozy, and is the primary evidence in suggesting that people may have been isolating 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 hardly seems possible that yuremamine could survive the extraction process.8,20,24,26

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 (Figures 9, 10). And there's that handy hydroxyl adjacent 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. I should also note that I'm not particularly qualified to propose a mechanism to either proposed 350.1 m/z compound, so it's difficult to tell how reasonable the assignment may be. Nevertheless, it would not be surprising if the molecule giving rise to this peak turns out to play a critical role in the psychoactivity of the jungle spice.


Figure 9. A couple proposed breakdown products of yuremamine, both would have molecular ion at 350.1 m/z


Figure 10. 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.8 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.8 This has led to the speculation that yuremamine is subject to degradation under most extraction conditions, particularly under high temperatures or alkaline environments.8,20,24,26 Vepsäläinen et al obtained an LC-MS spectrum of yuremamine, presented here for comparison (Figure 11).


Figure 11. LC-MS of Yuremamine (from Isolation and Characterization of Yuremamine)8​



Finally, we have a more recent report of GC-MS analysis run on the red spice:



This is a confounding result. The material was a red crystalline solid isolated based on its insolubility in hexane, which certainly sounds like jungle spice.19,24 We would expect very little of the material to 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.31 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.31 Or for whatever reason, the red component may not be amenable to GC-MS; based on the presence of more diverse peaks in LC-MS spectra, I tend to lean toward this possibility.

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.31 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 possibility, 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".31 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




Figure 12. 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:




Figure 13. Dozuki's TLC plates, #14, #12, and #18 (from left to right)​

And some further comments:





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 root bark 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.6 On the other hand, there are some indications that the term M tenuiflora may sometimes be applied to another Mimosa tree which does not have white blooms.19,29

In Mexico, following some catastrophic events in the '80s, the tannins in M tenuiflora root bark, called "tepescohuite", were 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 some 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 appearances, someone may have unknowingly or unscrupulously begun propagating another species as tepescohuite (Figure 14). On the other hand, I've seen some popular speculation that the Mexican root bark has a higher alkaloid content, so the possibility of a misidentification doesn't necessarily mean an inferior product for extracting purposes.28


Figure 14. Images associated with Mexican tepescohuite​

Also casting doubt on the identity of the root bark are the seeds. Consider what Torsten of Shaman Australis had to say a couple years ago:



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.19,20,34 At present, though at least one vendor has begun selling seeds that actually give rise to a Mimosa hostilis tree, most of what's available produces other Mimosa species, particularly M verrucosa.29

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.1,21 Consider the following quote from a 1998 MAPS Newsletter



In years past, there were misidentified seeds that produced Mimosa pudica or even Mimosa scabrella, but these appear to have faded from the marketplace.34 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 root bark, but unable to acquire legitimate seeds from the same source.20 On top of this, Torsten of Shaman Australis reports having seen a photo of the Mimosa plantation from which a major vendor obtains its root bark, and the flowers on the trees were pink.19,21

Mimosa tenuiflora has white flowers. It does not have pink flowers, or purple flowers, or yellow flowers. Any botanical reference will confirm this fact. Theorizing about a pink-flowering subspeciesof tenuiflora, as some forum members have, is entirely inconsistent with the established botanical definitions.

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 root bark that's being imported.



V.2 So what have people 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).1,21 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. But considering the scarcity of genuine seeds, I'd be hesitant to speculate that genuine M hostilis root bark is prevalent on the market.19,20 Further, it seems very 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.20

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've only heard a few reports of bunk batches of bark being sold a few years ago. These would extract to yield a clean white material with the physical appearance of DMT, but produced no effects when smoked, possibly indicating that the root bark used was from another species.19,20 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%). It is worthwhile to note here that at least one vendor (JLF) candidly admitted to selling Mimosa hostilis stem bark, which is of a substantially different chemical composition than the root bark.21

So for those who are concerned solely with extracting the N,N-DMT, the short answer is: No, it doesn't really matter whether the root bark 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 root bark, 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 root bark.7 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 root bark 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 simply 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.10 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 available root bark 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.6 The individuals who were unsuccessful may have been using M verrucosa while Ott was using M tenuiflora.



Literature References

1. Barbosa, Yatra-W.M. da Silveira. 1998. "Jurema Ritual in Northern Brazil." MAPS 8(3): 27-29.

2. Brandt, Simon D. et al. 2008. "N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis." J Pharm Biomed Anal. 47(1):207-12.

3. Buchanan MS, Carroll AR, Pass D, Quinn RJ. 2007. "NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa." Magn Reson Chem. 45(4):359-61.

4. Miller, M, et al. 2003. "3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies." Vet Pathol. 40:363-70.

5. DeKorne, Jim. 1996. "Mimosa hostilis: A Potent New Ayahuasca Analog." Entheogen Review 5(4):9.

6. Ott, J., Trout, K., Aardvark, D. 1999. "Mimosa Active Without MAOI?" Entheogen Review 8(1):22-24.

7. Trout, K. 2007. Ayahuasca: alkaloids, plants & analogs. Retrieved from the Erowid Web site: http://www.liu.edu/cwis/cwp/library/workshop/citapa.htm.

8. Vepsäläinen JJ, Auriola S, Tukiainen M, Ropponen N, Callaway JC. 2005. "Isolation and characterization of yuremamine, a new phytoindole." Planta Med. 71(11):1053-7.


Internet Forum References

9. Anima (@ Entheogen.com Forums). 2007. "MHRB, yellow oil and dmt-n-oxide." entheogen.com.

10. Doctorcito (@ Ayahuasca Forums). 2006. "Yuremamine: Solving the Mystery of Jurema Preta?" http://forums.ayahuasca.com/phpbb/viewtopic.php?t=9912.

11. DonPeyote (@ Drugs-Forum). 2006. "Jungle DMT?" http://www.drugs-forum.co.uk/forum/showthread.php?t=26468.

12. Dozuki (@ Entheogen.com Forums). 2006. "MHRB H2O/MeOH Extraction & TLC." entheogen.com.

13. Dravidian (@ Entheogen.com Forums). 2006. "DMT melted?!" entheogen.com.

14. Entheogenist (@ DMT-Nexus Forums). 2007. "So I extracted the red DMT..." http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=1678.

15. Fuego (@ DMT-Nexus Forums). 2007. "Doing xylol extraction." http://www.dmt-nexus.me/phpBB2/viewtopic.php?t=757.

16. Heyoka (@ DMT-Nexus Forums). 2007. "Yellow Oil = DMT-N-Oxide?" http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=4310.

17. Lemmiwinks (@ Entheogen.com Forums). 2007. "Red Spice?" entheogen.com.

18. Lemmiwinks (@ Entheogen.com Forums). 2007. "DMT possibly changing?" entheogen.com.

19. Marsofold (@ The Nook Forums). 2005. "Extraction Of An Alternate Alkaloid From Mimosa." Contact Support.

20. Marsofold (@ Drugs-Forum). 2005. "The Other Alkaloid In Mimosa Hostilis." http://www.drugs-forum.co.uk/forum/showthread.php?t=13507.

21. Marsofold (@ Mycotopia Forums). 2005. "False Mimosa Hostilis Being Sold?" http://forums.mycotopia.net/dmt-spice/6258-false-mimosa-hostilis-being-sold.html.

22. MisterGypsy (@ DMT-Nexus Forums). 2007. "Red Spice Experiences." Red Spice Experiences - DMT Experiences - Welcome to the DMT-Nexus.

23. Napolean Blownapart (@ Ayahuasca Forums). 2003. "Hummingbirds brew - Phosphoric tec." http://forums.ayahuasca.com/phpbb/viewtopic.php?t=851.

24. Noman (@ DMT-Nexus Forums). 2006. "Dark DMT - the Other Alkaloid." Dark DMT - the Other Alkaloid - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus.

25. Noman (@ DMT-Nexus Forums). 2006. "Dark DMT." http://www.dmt-nexus.me/phpBB2/viewtopic.php?t=78.

26. Noman (@ The Lycaeum Forums). 2006. "Dark DMT." http://forums.lycaeum.org/index.php/topic,17215.0.html.

27. Salvia_Antics (@ DMT-Nexus Forums). 2007. "Dark DMT Extraction?" http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=12003.

28. TheAngryGolfer (@ Entheogen.com Forums). 2006. "Orange spice?" entheogen.com - Ce site web est à vendre ! - Ressources et information concernant entheogen Resources and Information..

29. Entropymancer (@ The Corroboree Forums). 2008. "Concerning the Identity of commercial Mimosa root bark" Concerning the Identity of commercial Mimosa root bark.

30. AttentionAllShipping (@ DMT-Nexus Forums). 2008. Very different experiences with dark dmt goo." very different experiences with dark dmt goo - DMT Experiences - Welcome to the DMT-Nexus

31. Entropymancer (@ DMT-Nexus Forums). 2008. "'Jungle Spice' - Mystery Alkaloids of Mimosa Root Bark." "Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark - DMT Discussion - Welcome to the DMT-Nexus.

32. Delafonze19; personal communication, March 17, 2008.

33. Noman; personal communication, February 26, 2008.

34. Torsten; personal communication, February 24, 2008.

35. WarrenSaged; personal communication, February 24, 2008.

36. Anonymous; personal communication, June 15, 2008.

(Last edit: 6/27/2008.)
Click to expand...
Oh this is gold! Found it 16 years later😄
 
dimensionseeker2000 said:
Oh this is gold! Found it 16 years later😄
Click to expand...

Entropymancer said:
"Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark

by Entropymancer​

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


So just what is Jungle spice?

Jungle spice is one of many names that have been applied to an intriguing non-DMT alkaloid fraction that can be isolated from much of the commercially available Mimosa root bark (See V. Botanical Confustication).10,11,17 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 N,N-DMT in addition to the more mysterious alkaloids; 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.15,19 Which compounds are actually isolated depends on some several of the following factors: the source and botanical identity of the root bark, the conditions of cultivation/harvest, and various pH, temperature, and airflow considerations throughout the extraction process.10,11,24,26 About all that is certain about it at this point is that it contains some psychoactive material that 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 2005.8,20,24 Looking at the evidence, this scenario appears exceedingly unlikely based on yuremamine's known instability to base and speculated instability to heat.8,24 It can't yet be ruled out completely, but there remains a substantial body of evidence against this identification. Until an LC-MS 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, and clear the way for future investigators to finish unraveling this mystery.



Table of Contents
I. Diversity of the Extracted Compounds
- I.1 Red/Brown Crystalline Goos
- I.2 Tan Waxes
- I.3 "Kokusaginine"
- I.4 Yellow Oils
- I.5 General Comments on "Colored Spice"
- - I.5.A Old Spice
- - I.5.B Other Considerations, Botanical and Synthetic
- - I.5.C Evaporated Spice
- - I.5.D Alternate Solvents
- - I.5.E Odds and Ends
II. Experiences
- II.1 Experiences Smoking the Red Crystalline Goo
- II.2 Experiences Smoking Tan Waxes
- II.3 Experiences Smoking Colored DMT
- II.4 Reports of Oral Activity
- II.5 Reports of Changes in Alkaloid Activity with Age and Heat
- - II.5.A Experiences with Old Spice
III. Isolation Techniques
- III.1 Entheogenist's Jungle Tek
- III.2 Critical Switch's Tek
- III.3 Isolation of "Kokusaginine"
- III.4 Delafonze19's Preparation of Yellow Spice Oil
- III.5 Alternate "Dark Spice" Isolation
IV. The Hard Data
- IV.1 Mass Spectrometry Analysis
- IV.2 TLC Analysis
V. Botanical Confustication
- V.1 Hostilis? Tenuiflora? Verrucosa?!?!
- V.2 So what have people been extracting from, and does it matter?





I. Diversity of the Extracted Compounds

Probably the biggest issue complicating the mystery of jungle spice is the sheer diversity of compounds that can be extracted using apparently identical methods.14,15,17,19,22,24,26,30 Based on their physical properties, we can classify three distinct types of material that can come from the xylene/toluene pull. Considering the reported pharmacological activity of these materials in human subjects, the picture becomes much more complicated.



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."
Entheogenist14

"Could you describe the material? My friend's has the consistency of a soft crayon and is brick red."
Noman14

"The junglespice I got is just like a piece 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."
QuantumBrujo14

"Swim succeeded in pulling the red spice. It's a dark , deep crimson color , almost the color of dried blood."
Spicemeister17​


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, in some cases washing the dark gunk with naphtha leaves behind a red solid which is insoluble in the naphtha (Figure 1). This red material has been isolated both by straight-to-base extraction and by acid/base extraction.14,19,22,24,26,33

The crude extract is invariably an impure mixture. In most cases, pulling the alkaline aqueous phase with xylene extracts a bright yellow color into the solvent; the red pigment isn't seen until the solvent is evaporated.24,28 When the DMT and other impurities are removed from the crude extract by a warm wash in an aliphatic hydrocarbon (naphtha, heptane, etc.), several extractors report that the recovered DMT crystals remain stained yellow.17,24 This yellow fraction of the jungle spice that's soluble in warm naphtha could be several different things (see I.4 Yellow Oils).

It is important to note that some people obtain an explicitly brown goo from the xylene pull, with no indication of red coloration whatsoever (Figure 2).24,17,22,24 Although they may appear similar to the crude red/brown goo on initial inspection, exclusively brown extracts appear to yield a different product, distinct from the red material (see I.2 Tan Waxes). 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.24

Of course, we can't rule out the possibility that the red material may be a mixture of multiple alkaloids. For example, it seems plausible that the red material might have essentially the same chemical composition as the tan waxes, with the addition of a small amount of a red pigment that's responsible for the differences in appearance (color and consistency) between the red material and the tan waxes.


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."
Archaea17

"[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."
Noman24​


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 vary widely from extraction to extraction.33 It is obtained exactly the same way as the red material above; an aqueous hydroxide solution containing mimosa alkaloids is extracted with several 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 the crude jungle spice. Washing this crude material with hot naphtha yields a waxy solid, ranging in color from tan to orange to brown.24,15,22,17

This material has been isolated from both acid/base and straight-to-base procedures.24,17,33 Its isolation has also sometimes been positively correlated with heating the naphtha pulls prior to the aromatic pull, but unless further evidence corroborates it, this will be considered to be coincidental.24 Again, we'll run into some further confusion when we look at the reported pharmacological activity of this material, indicating that there may be more than one compound here. Specifically, this is the fraction of jungle spice which is most frequently reported to change activity over time, indicating that some chemical reaction (presumably oxidation) is occurring.25,15,13



I.3 "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 activity.9,17,24,31 Generally these posters cite the 1999 Entheogen Review article where Jonathan Ott and K. Trout are asked their opinions on the matter.6 Unfortunately, these people seem to have read no further than the second paragraph before leaping to this completely unfounded conclusion. To summarize:

The article begins with a question from a reader, "J.S, OR".


K. Trout was asked about this, to which he replied


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


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 appear to substantiate the latter explanation.8 Regardless, I hope that this can put to rest the idea that the soporific component that has been isolated from Mimosa root bark is kokusaginine.

Based on physical descriptions as well as reports of its effects, it appears that the compound that people have typically been calling kokusaginine is identical with the tan waxy material, and is usually described as being very hard.17,24 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.11,13,17,24,26 (For an account of the isolation of this fraction, see III.3 Isolation of "Kokusaginine")



I.4 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 Member26

"It's yellowish. Even a yellow crystal. Smells the same as DMT with a musty overtone."
Heyoka16

"After two recrystallizations on the N,N- that came out with [the jungle spice], swim tells me it is irretrievably stained yellow and resembles egg yolk."
Spicemeister17​


This is by far the most ambiguous 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.9,12,16,24 When spice is extracted with xylene/toluene or diethyl ether (without using naphtha first), it also tends to come out with a bright yellow-orange discoloration.13,15,17,24,28 The most substantial evidence that there is more than one compound in the yellow oil is the ambiguous solubility of the material. Yellow oil is separated from jungle spice based on its solubility in naphtha, while at the same time a yellow oil can be removed from DMT (extracted by standard straight-to-base methods) based on it's insolubility in hot naphtha. Clearly these must be different yellow oils.

To further complicate the issue, it's very difficult to isolate the yellow oil on its own. 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.9,16,24 These yellow crystals are sometimes reported to be qualitatively better in terms of effects than pure DMT.16,28,32 Also, when washing the crude jungle spice extract with warm naphtha, some extractors report that any N,N-DMT they recover from this process is strongly yellow-colored, and that this pigment seems impossible to remove by typical purification methods. Unfortunately I haven't been able to find any experience reports specifically using such yellow-stained DMT.17,24

Investigating the possibility of the yellow oil being DMT N-Oxide, I found a 2005 paper reporting the isolation of this compound 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.3 This is only useful in that someone with access to proton NMR spectroscopy who obtains a sample of yellow "oxidized" DMT could use this information to conclusively establish the identity of this material. One home extractor who did some TLC analysis on whole and purified extracts of Mimosa root bark described DMT N-oxide as a yellow oil, though I can't corroborate this decription in the published literature.12 On a related note, one home extractor has discovered a method for reliably converting bright white spice into a yellow oil (without using any synthetic reagents); the nature of the process indicates that the yellow oil it isolates is in fact an oxidized derivative of DMT (see III.4 Delafonze19's Preparation of Yellow Spice Oil).32

Looking at the Radio879's LC-MS 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 side-product of the extraction process.19 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.8 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 root bark (see V. Botanical Confustication)19,29



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."24

"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."24

"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."24​

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.11,13,16,17,24,27,28 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 the 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 definitely 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 Bong15​

Probably the simplest form of colored DMT comes from samples that were originally pure white spice. As the samples age, they turn orange and waxy over time.16,18 There seems to be substantial disagreement over the amount of time necessary for this process to occur.16 Some people report a change in color become noticeable after several weeks to a month, while others have samples that are over a year old and still without discoloration.16,18 One potential determining factor is the amount and type of impurities present in the sample. This is corroborated by differences in the DMT's shelf-life positively correlating with differences in the clean-up process used to extract it; multiple samles which turned color rapidly with age had not been washed with ammonia or bicarbonate, while the year-old sample had.16 This would tend to indicate that either residual hydroxide from the extraction, or perhaps some trace phytochemical that the alkaline polar wash removes, is responsible for the change in the DMT as it ages. Anecdotal evidence indicates that higher temperatures speed this degradation process.13,18 It is unknown whether environmental factors such as air moisture may play a role in the rate of degradation.

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 an oxidation product of little consequence. 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 its 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 will lead to a more rapid orange-ing of the spice. This explanation is consistent with observations that have been made on yellow oil, but at present remains entirely speculation.

On the other hand, it's very 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 that started out white?). 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.18,24 It has been suggested that the difference between fresh spice and very old spice is like the difference between fresh spice, and the residue that can be scraped from the inside of the freebase pipe used to smoke it.13

Reports of more drastic changes in the appearance and effects of DMT due to exposure to higher temperatures are covered in II.5.A Experiences with Old Spice.



I.5.B Other Considerations, Botanical and Synthetic

When talking about old spice from back in the '60s, '70s, and '80s, it's important to recall that we're not necessarily talking about the beautiful snowflakes of DMT that any Joe Blow can now extract from M hostilis root bark. It was only in the winter of 1996 that the Entheogen Review reported Mimosa hostilis as "a potent new ayahuasca analog."5 Most extraction processes purveyed on the internet in the early- to mid-'90s were aimed primarily at obtaining a smokable DMT goop. As far as I know, there isn't a lot of clear information on whether the DMT circulating in previous decades was of synthetic origin, or extracted from plant materials. These are important considerations, as the initial purity and the chemical properties of the contaminants are key factors in determining how the material ages. Most of the discussion here assumes that the extraction was done by processes which have been popular among internet extractors.



I.5.C Evaporated Spice

Another very common form of colored spice results from people evaporating their nonpolar solvent instead of freeze-precipitating.9,28 The yellow pigment contained in spice that has been extracted with an aliphatic hydrocarbon and collected by evaporation appears to just be inconsequential trace impurities. Most likely these are fats from the root bark. It is reportedly harsher to smoke, but roughly the same potency as white spice.9,28 This yellow fraction can be removed from the spice by recrystallization.24 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 evaporation conditions. People report a much more yellow oily product when the solvent is evaporated with high airflow from a fan, particularly with warmer temperatures.9,24 Others have obtained yellow crystals by melting off-white spice in an attempt to do a "solvent-less recrystallization".32 Yellow crystals obtained in this fashion are reported to be qualitatively different than plain spice, and slightly more potent.9,28,32 Based on this information, it sounds like these methods are producing DMT which contains the type of yellow oil I suspect to be DMT N-oxide. Delafonze19 has reported happening on a method for reliably converting white DMT to the potent yellow oil (see III.4 Delafonze19's Preparation of Yellow Spice Oil).32



I.5.D 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), or aromatics like xylene and toluene.24,28 It's also entirely conceivable that decades ago, extractors might have used benzene as their nonpolar solvent. All of these are effective extraction solvents for pulling DMT, but as we've seen, they're less specific and pull other fractions. All have been reported to yield yellow or even orange spice.11,17,24,28 It will be easiest to consider each solvent separately.



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 of spice with an aliphatic hydrocarbon.19,24,14 It's therefore reasonable that they could be used as the primary extraction solvent to pull a similar mixture, but containing a great deal more DMT.19,28 One experimenter did just that:



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. Another extractor also obtained an orange material using xylene as the extraction solvent, and had a sample of this analyzed by LC-MS; this has allowed for some discussion of the identity and abundance of the other compounds extracted by this solvent (see IV.1 Mass Spectrometry Analysis).19



Ether

There have periodically been reports of using ether, or a binary solvent of ether/heptane, as an extraction solvent.17,24 This invariably leads to a product with yellow discoloration. Since the ether is evaporated to yield spice, it's not surprising that the product is yellow; we might expect some 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 along with the DMT, so it's possible that the yellow color in ether extracts is a trace amount of that jungle spice fraction. Based on reports of ether extracts smelling "strongly floral", it's also quite possible that the ether is extracting some skatole (see IV.1 GC/MS Analysis). It is curious to note that, while ether, dichloromethane, and aromatic solvents have all been reported to pull jungle spice, ether is the only one of these solvents not reported to produce orange crystals when used alone as an extraction solvent. This is particularly interesting when one considers that ether is also the solvent associated with the hard tan wax some have called "kokusaginine", and has never been reported to extract a red product when used as a solvent to obtain jungle spice.17,24



Dichloromethane

This solvent is recommended by some 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.2,3 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 be colored for the same reason as the orange crystals extracted by xylene. There's also the possibility that the color results from a pigment pulled specifically by the DCM. Finally, there's the possibility 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."2

I was unable to turn up any reports on the qualitative effects of orange spice extracted with DCM. This compound is unlikely to be psychoactive based on its presumed low bioavailability; potential toxicity concerns are unknown. One extractor decided to perform some experiment to establish whether the orange color was extracted from the plant, or whether it might be the rearranged N-chloromethyl- derivative. After obtaining an orange material from a Mimosa root bark extraction with DCM, he tried extracting Chacruna leaves by the exact same process, also using DCM, and found the result in the latter case to be pure white DMT.11 This result strongly indicates that the formation of rearrangement products is not of major concern when using DCM, and the difference in the product using this solvent is a result of its lower selectivity as compared to typical alkane solvents.





I.5.E Odds and Ends

The use of plants other than M hostilis as sources of DMT was alluded to above; this provides another possible source of reported orange DMT. Many species of Acacia, for example, can yield an orange crystalline product on extraction. 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.3,24 Specifically, some of the color might even come from 5-MeO-DMT, which is substantially more potent than DMT by weight. Further, a colleague who recently encountered some bright red DMT inquired and found that it had been extracted from a species of phalaris grass.36

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 unmistakably purple. I cannot conceive of this coloration having come from any of the materials discussed above. Until some experiences come in with this material, I'd say it's probably best to recrystallize any such spice you happen to run across.

I have also seen infrequent 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 a blue non-volatile solvent-additive: yellow + blue = green. Long story short: avoid "green spice" like the plague.




II. Experiences

Below are a collection of experiences that people have had consuming the jungle spice. By and large, the method of administration in the reports was smoking, but there are a few reports of oral consumption of the jungle spice (either by itself or in an attempt to potentiate DMT). The reports do not yet allow us to paint a conclusive picture about the activity of these compounds, mostly owing to the tremendous variability in the extracted material. Where they have their values is in providing the real heart of the evidence that there is an as-yet unidentified psychoactive compound at work here. The sheer volume of reports detailing different or stronger effects at lower dosages than are used with ordinary DMT is overwhelming evidence that there is an unsolved piece in this puzzle.

I've tried to preserve all their original form and content, but I have made a few edits for punctuation, spelling, and grammar.


II.1 Experiences Smoking the Red Crystalline Goo























II.2 Experiences Smoking Tan Waxes











II.3 Experiences Smoking Colored DMT

There don't appear to be any experience reports by folks who've extracted and purified a yellow oil. However, there are some experience reports available with orange or yellow "colored spice", which are discussed in Section I.5.









II.4 Reports of Oral Activity











II.5 Reports of Changes in Alkaloid Activity with Age and Heat

Again it will be convenient to organize these reports by the starting material. Since most or all samples of jungle spice appear to contain some residual DMT, it will be useful to first address changes in activity over time observed in "pure" (white) spice over time. The preliminaries of this issue were discussed above (see Old Spice), so the subsequent discussion will be confined to the drastic change in activity that seems to occur when mild to moderate environmental heat is involved. After that, we'll consider the reports of changing effects over time as they pertain to the jungle spice. No reports could be found on the effects of the red crystalline form of jungle spice changing over time, but the phenomenon was reported several times with the tan wax fraction.11,17,24



II.5.A Experiences with Old Spice













II.5.B Experience with Tan Waxes Over Time








III. Isolation Techniques

None of the following extraction methods are mine. Credit is given where credit is due.


III.1 Entheogenist's Jungle Tek24




III.2 Critical Switch's Tek19

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 primarily for historical relevance.





III.3 Isolation of "Kokusaginine"24

As discussed above, this fraction is almost certainly not kokusaginine, 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, though there is some evidence it may leave behind the red material that aromatic solvents will pull.17,24 The original author is unknown to me; this was cross-posted by Implants.





III.4 Delafonze19's Preparation of Yellow Spice Oil32

After freeze-precipitating the DMT, the naphtha was poured off and the solids allowed to dry in a jar. Hot water is then run over the jar, melting the spice. This process promotes the conversion of the white crystals into a yellow oily crystal which is reportedly more subjectively enjoyable than white spice. If the yellow oily crystals are left out with moderate exposure to air for a week, the process appears to proceed further towards completion, turning the material into a yellow goo.



III.5 Alternate "Dark Spice" Isolation26

The original author is unknown. This was cross-posted by Orbit:







IV. The Hard Data

Attempts have periodically been made to shed light on the nature of jungle spice by use of GC-MS, LC-MS, or TLC.12,13,19,31 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.13,19 The other major conclusion that seems to have come out of these attempts is establishing that no unique chemicals besides DMT can typically be seen in GC-MS analyses, while LC-MS shows a wider range of compounds.8,19,31


IV.1 Mass Spectrometry Analysis


Figure 5. 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 A5)7​

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 5).7 The initial extraction was done 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 any 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."7

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.7

The extracted sample also appears to be fairly clean. Extremely clean when we consider that it was collected 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 could easily be 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.7



Next we consider a crude extract of the “jungle” alkaloids. This analysis was communicated by Radio879 from the Nook.19 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."19 (See Figure 6) 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.


Figure 6. Radio879's LC-MS of an unpurified xylene pull, extracted by an acid/base process.31​


130.1 m/z

This peak had me mystified for the longest time. Too small to be a tryptamine; barely large enough to be an indole. But 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 7).7




Figure 7. 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 targeting 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.4 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 plausible. 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 (Figure 8.). Incidentally, DMT N-oxide and DMT have been shown to enzymatically interconvert in lower mammals.


Figure 8. DMT N-Oxide​



350.1 m/z

This one is a doozy, and is the primary evidence in suggesting that people may have been isolating 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 hardly seems possible that yuremamine could survive the extraction process.8,20,24,26

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 (Figures 9, 10). And there's that handy hydroxyl adjacent 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. I should also note that I'm not particularly qualified to propose a mechanism to either proposed 350.1 m/z compound, so it's difficult to tell how reasonable the assignment may be. Nevertheless, it would not be surprising if the molecule giving rise to this peak turns out to play a critical role in the psychoactivity of the jungle spice.


Figure 9. A couple proposed breakdown products of yuremamine, both would have molecular ion at 350.1 m/z


Figure 10. 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.8 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.8 This has led to the speculation that yuremamine is subject to degradation under most extraction conditions, particularly under high temperatures or alkaline environments.8,20,24,26 Vepsäläinen et al obtained an LC-MS spectrum of yuremamine, presented here for comparison (Figure 11).


Figure 11. LC-MS of Yuremamine (from Isolation and Characterization of Yuremamine)8​



Finally, we have a more recent report of GC-MS analysis run on the red spice:



This is a confounding result. The material was a red crystalline solid isolated based on its insolubility in hexane, which certainly sounds like jungle spice.19,24 We would expect very little of the material to 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.31 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.31 Or for whatever reason, the red component may not be amenable to GC-MS; based on the presence of more diverse peaks in LC-MS spectra, I tend to lean toward this possibility.

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.31 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 possibility, 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".31 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




Figure 12. 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:




Figure 13. Dozuki's TLC plates, #14, #12, and #18 (from left to right)​

And some further comments:





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 root bark 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.6 On the other hand, there are some indications that the term M tenuiflora may sometimes be applied to another Mimosa tree which does not have white blooms.19,29

In Mexico, following some catastrophic events in the '80s, the tannins in M tenuiflora root bark, called "tepescohuite", were 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 some 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 appearances, someone may have unknowingly or unscrupulously begun propagating another species as tepescohuite (Figure 14). On the other hand, I've seen some popular speculation that the Mexican root bark has a higher alkaloid content, so the possibility of a misidentification doesn't necessarily mean an inferior product for extracting purposes.28


Figure 14. Images associated with Mexican tepescohuite​

Also casting doubt on the identity of the root bark are the seeds. Consider what Torsten of Shaman Australis had to say a couple years ago:



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.19,20,34 At present, though at least one vendor has begun selling seeds that actually give rise to a Mimosa hostilis tree, most of what's available produces other Mimosa species, particularly M verrucosa.29

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.1,21 Consider the following quote from a 1998 MAPS Newsletter



In years past, there were misidentified seeds that produced Mimosa pudica or even Mimosa scabrella, but these appear to have faded from the marketplace.34 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 root bark, but unable to acquire legitimate seeds from the same source.20 On top of this, Torsten of Shaman Australis reports having seen a photo of the Mimosa plantation from which a major vendor obtains its root bark, and the flowers on the trees were pink.19,21

Mimosa tenuiflora has white flowers. It does not have pink flowers, or purple flowers, or yellow flowers. Any botanical reference will confirm this fact. Theorizing about a pink-flowering subspeciesof tenuiflora, as some forum members have, is entirely inconsistent with the established botanical definitions.

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 root bark that's being imported.



V.2 So what have people 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).1,21 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. But considering the scarcity of genuine seeds, I'd be hesitant to speculate that genuine M hostilis root bark is prevalent on the market.19,20 Further, it seems very 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.20

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've only heard a few reports of bunk batches of bark being sold a few years ago. These would extract to yield a clean white material with the physical appearance of DMT, but produced no effects when smoked, possibly indicating that the root bark used was from another species.19,20 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%). It is worthwhile to note here that at least one vendor (JLF) candidly admitted to selling Mimosa hostilis stem bark, which is of a substantially different chemical composition than the root bark.21

So for those who are concerned solely with extracting the N,N-DMT, the short answer is: No, it doesn't really matter whether the root bark 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 root bark, 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 root bark.7 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 root bark 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 simply 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.10 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 available root bark 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.6 The individuals who were unsuccessful may have been using M verrucosa while Ott was using M tenuiflora.



Literature References

1. Barbosa, Yatra-W.M. da Silveira. 1998. "Jurema Ritual in Northern Brazil." MAPS 8(3): 27-29.

2. Brandt, Simon D. et al. 2008. "N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis." J Pharm Biomed Anal. 47(1):207-12.

3. Buchanan MS, Carroll AR, Pass D, Quinn RJ. 2007. "NMR spectral assignments of a new chlorotryptamine alkaloid and its analogues from Acacia confusa." Magn Reson Chem. 45(4):359-61.

4. Miller, M, et al. 2003. "3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies." Vet Pathol. 40:363-70.

5. DeKorne, Jim. 1996. "Mimosa hostilis: A Potent New Ayahuasca Analog." Entheogen Review 5(4):9.

6. Ott, J., Trout, K., Aardvark, D. 1999. "Mimosa Active Without MAOI?" Entheogen Review 8(1):22-24.

7. Trout, K. 2007. Ayahuasca: alkaloids, plants & analogs. Retrieved from the Erowid Web site: http://www.liu.edu/cwis/cwp/library/workshop/citapa.htm.

8. Vepsäläinen JJ, Auriola S, Tukiainen M, Ropponen N, Callaway JC. 2005. "Isolation and characterization of yuremamine, a new phytoindole." Planta Med. 71(11):1053-7.


Internet Forum References

9. Anima (@ Entheogen.com Forums). 2007. "MHRB, yellow oil and dmt-n-oxide." entheogen.com.

10. Doctorcito (@ Ayahuasca Forums). 2006. "Yuremamine: Solving the Mystery of Jurema Preta?" http://forums.ayahuasca.com/phpbb/viewtopic.php?t=9912.

11. DonPeyote (@ Drugs-Forum). 2006. "Jungle DMT?" http://www.drugs-forum.co.uk/forum/showthread.php?t=26468.

12. Dozuki (@ Entheogen.com Forums). 2006. "MHRB H2O/MeOH Extraction & TLC." entheogen.com.

13. Dravidian (@ Entheogen.com Forums). 2006. "DMT melted?!" entheogen.com.

14. Entheogenist (@ DMT-Nexus Forums). 2007. "So I extracted the red DMT..." http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=1678.

15. Fuego (@ DMT-Nexus Forums). 2007. "Doing xylol extraction." http://www.dmt-nexus.me/phpBB2/viewtopic.php?t=757.

16. Heyoka (@ DMT-Nexus Forums). 2007. "Yellow Oil = DMT-N-Oxide?" http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=4310.

17. Lemmiwinks (@ Entheogen.com Forums). 2007. "Red Spice?" entheogen.com.

18. Lemmiwinks (@ Entheogen.com Forums). 2007. "DMT possibly changing?" entheogen.com.

19. Marsofold (@ The Nook Forums). 2005. "Extraction Of An Alternate Alkaloid From Mimosa." Contact Support.

20. Marsofold (@ Drugs-Forum). 2005. "The Other Alkaloid In Mimosa Hostilis." http://www.drugs-forum.co.uk/forum/showthread.php?t=13507.

21. Marsofold (@ Mycotopia Forums). 2005. "False Mimosa Hostilis Being Sold?" http://forums.mycotopia.net/dmt-spice/6258-false-mimosa-hostilis-being-sold.html.

22. MisterGypsy (@ DMT-Nexus Forums). 2007. "Red Spice Experiences." Red Spice Experiences - DMT Experiences - Welcome to the DMT-Nexus.

23. Napolean Blownapart (@ Ayahuasca Forums). 2003. "Hummingbirds brew - Phosphoric tec." http://forums.ayahuasca.com/phpbb/viewtopic.php?t=851.

24. Noman (@ DMT-Nexus Forums). 2006. "Dark DMT - the Other Alkaloid." Dark DMT - the Other Alkaloid - Advanced/Enhanced chemistry - Welcome to the DMT-Nexus.

25. Noman (@ DMT-Nexus Forums). 2006. "Dark DMT." http://www.dmt-nexus.me/phpBB2/viewtopic.php?t=78.

26. Noman (@ The Lycaeum Forums). 2006. "Dark DMT." http://forums.lycaeum.org/index.php/topic,17215.0.html.

27. Salvia_Antics (@ DMT-Nexus Forums). 2007. "Dark DMT Extraction?" http://www.dmt-nexus.me/phpBB2/viewtopic.php?p=12003.

28. TheAngryGolfer (@ Entheogen.com Forums). 2006. "Orange spice?" entheogen.com.

29. Entropymancer (@ The Corroboree Forums). 2008. "Concerning the Identity of commercial Mimosa root bark" Concerning the Identity of commercial Mimosa root bark.

30. AttentionAllShipping (@ DMT-Nexus Forums). 2008. Very different experiences with dark dmt goo." very different experiences with dark dmt goo - DMT Experiences - Welcome to the DMT-Nexus

31. Entropymancer (@ DMT-Nexus Forums). 2008. "'Jungle Spice' - Mystery Alkaloids of Mimosa Root Bark." "Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark - DMT Discussion - Welcome to the DMT-Nexus.

32. Delafonze19; personal communication, March 17, 2008.

33. Noman; personal communication, February 26, 2008.

34. Torsten; personal communication, February 24, 2008.

35. WarrenSaged; personal communication, February 24, 2008.

36. Anonymous; personal communication, June 15, 2008.

(Last edit: 6/27/2008.)
Click to expand...
Thanks so much for the work!
 
FWIW (and not sure if anybody can fix it) but the formatting of the OP here seems to have gone sideways at some point, the text is all struckthrough from about halfway through section 1.3 makes it a bit challenging to read (had to copy-paste it to a plaintext document) ;).

Ah, that's better, didn't notice the attached PDF ;)
 
somerandompsychonaut said:
FWIW (and not sure if anybody can fix it) but the formatting of the OP here seems to have gone sideways at some point, the text is all struckthrough from about halfway through section 1.3 makes it a bit challenging to read (had to copy-paste it to a plaintext document) ;).

Ah, that's better, didn't notice the attached PDF ;)
Click to expand...
Thanks for bringing this up; I've now removed the strikethrough in the OP (although the structure for yuremamine still needs updating).
 
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