"Jungle Spice" -mystery Alkaloids of Mimosa Root Bark




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"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 isJungle 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



  1. IV. The Hard Data-IV.1 Mass Spectrometry Analysis-IV.2 TLC Analysis

  2. 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."

14

Entheogenist



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

14

Noman


"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."

14

QuantumBrujo



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

17

Spicemeister

The reddish brown crystalline goo that one can find pictures of floating around the internet are what I tend to think of as jungle spice, but washing this goo can yield a surprising diversity of products. As the above quotes indicate, 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)

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is the final product that was obtained from Figure 2 after the goo was washed with hot naphtha.

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."

17

Archaea


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

24

Noman


The name and the pictures say it all. This fraction is a very waxy solid, with coloration ranging from a light yellow/orange to a much darker brown. The exact color of this fraction appears to vary widely from

33

extraction to extraction.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,

24

but unless further evidence corroborates it, this will be considered to be coincidental.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



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asked their opinions on the matter.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":

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

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

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

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

“I've no idea whence derives the querist's notion that kokusaginine occurs in M. tenuiflora, and I am in agreement with K. Trout's remark in this regard, while it is a mystery to me why it would be assumed this compound possesses MAOI activity, nor indeed how this compound -or moclobemide, with which it is structurally unrelated -is "morphine-like," none of which has anything to do with the recondite pharmacology of jurema preta/ tepescohuite, in any case.

Perhaps there is some confusion here between the rutaceous kokusaginine [found in New Caledonian Dutaillyea spp., among others] and the so-called "kukulkanins" reported from powdered stem-bark of Mexican tepescohuite [misreported as Mimosa tenuefolia L. (sic): Journal of Natural Products 52(4): 864-867, 1989], also of obscure pharmacology. There is no reason to suppose this compound or any of the diverse saponins likewise reported from bark of Mexican tepescohuite show MAOI activity, and at least five phytochemical analyses of Brazilian jurema preta [mostly unpublished] have failed to show presence of §-carbolines

(Editor's note: Emphasis mine; I find this comment significant in light of some claims on the internet that the identity of the red pigment has been established firmly as a §-carboline) nor any other category of potent MAOI. Moreover, pharmacologically and pharmacodynamically, the psychoptic effects of cold-water, hand

squeezed and short-time-infused, aqueous extracts of simple pounded jurema preta root-bark prepared according to the traditional manner as documented in several Brazilian reports, bears no relation to the -to me -well-known pharmacology of the ß-carbolines and other MAOI...

Preliminary chemical evidence reveals rather the presence of several novel and yet-unidentified DMT adducts in jurema preta root-bark, apart from free DMT itself. Either these compounds show oral activity per se, not being substrate to gastric MAO, or rather show a higher affinity for the enzyme[s], serving thus as competitive inhibitors respective to DMT for its active site[s], in the manner that the ß-carbolines do. My current work strongly suggests the former conjecture is the more parsimonious.”

It'd have been nice if Mr. Ott explained why he feels the former explanation to be more parsimonious, as the isolation of yuremamine, with its intramolecular H-bonding, would appear to substantiate the latter

8

explanation.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."

26

Lycaeum Member



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

16

Heyoka


"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."

17

Spicemeister

This is by far the most ambiguous fraction that comes out of the xylene/toluene pull. Some of the yellowoils 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



3

data.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 description in the



12

published literature.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



32

Delafonze19's Preparation of Yellow Spice Oil).

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



19

that this chemical is generated as a side-product of the extraction process.It may exist in the bark as a trace component (there is a barely perceptible peak at 205.1 m/z in the VepsŠlŠinen paper reporting the characterization of yuremamine), though it's possible this trace peak was an artifact of the isolation



8

process as well.It's also possible that the sample analyzed in the paper was from a different subspecies, or even an entirely different Mimosa species than is typically purchased as 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

24

crystals."

"I have had the orange DMT that Terrence and old heads speak of. It is DIFFERENT than the snow white DMT people extract these days. People will say things like "it's impure, clean it" blah blah blah.

24

No. They've never had it then. It is the most ridiculously potent DMT SWIM has ever smoked.""Since 1999 there has been the reds also called purple by some, yellow, orange, and white spices available at music festivals, and have been kept underground till recently. At the last SCI shows in Red Rocks CO there was all colors available, being offered quite openly. You could smell that sweet plastic

24

smell every few 1000 feet while walking the lot."

There has been a great deal of discussion and speculation on "yellow DMT" and "orange DMT", some of which has been reported to be subjectively different than ordinary white DMT.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 !"

15

El Ka Bong

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



16 disagreement over the amount of time necessary for this process to occur.Some people report a change in color become noticeable after several weeks to a month, while others have 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

16

had.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

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