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"Jungle Spice" - Mystery Alkaloids of Mimosa Root Bark Options
 
Entropymancer
#1 Posted : 2/26/2008 3:18:01 AM

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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 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".
Quote:
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
Quote:
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:
Quote:
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 ß-carbolines (Editor's note: 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 ß-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 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:

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

Good quality Syrian rue (Peganum harmala) for an incredible price!
 
WSaged
#2 Posted : 3/3/2008 7:34:18 PM

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Great job Entropymancer!!!
Thanks for taking your time to put this together!!!

WS
All posts are fictional short stories depicting the adventures of WSaged!! None of these events have actually happened and any resemblance to any real persons or incidents is totally coincidence!!!!!!!!!!!!
 
El Ka Bong
#3 Posted : 3/3/2008 9:32:52 PM

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Excellent, new reading material ..! must print a copy for the files !
 
Entropymancer
#4 Posted : 3/4/2008 3:46:41 AM

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Well, when I started looking into it, I pretty quickly realized it was a complex enough issue that I'd forget 75+% of what I learned unless I wrote it down somewhere. And so putting it somewhere everyone else can enjoy it too made sense. There's still more to come, I've been putting an hour a night in on it (might as well make insomnia productive), so it will still be a few weeks until it's done.

If anyone sees their experience report up there and thinks I've misclassified the variety of jungle spice, please let me know.

Glad everyone else finds it as interesting as I do. Smile

(Also I'd appreciate if someone knows a better place to host the images in the document... drop me a PM)
 
The Traveler
#5 Posted : 3/4/2008 7:25:59 AM

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Entropymancer wrote:
(Also I'd appreciate if someone knows a better place to host the images in the document... drop me a PM)


Well, we can drop it on the DMT-Nexus. Pleased
I'll make a user-dir for you with ftp etc. Tonight you have your logon info (it's morning now and have to go to work).
 
burnt
#6 Posted : 3/13/2008 7:36:14 PM
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Hi I am new here. I got excited about the chemistry talk. Some guy i don't know well told me he can run GC-MS on this compound. He believes he has some of this so called jungle spice. It is a red crystalline thing that was originally oozy. After recrystallizing white crystals out of it he saved this other stuff. He believes if his bad memory serves him right that it came from toluene or diethyl ether pull from an acid base extraction. He was wondering what it could have been.

I cant see the images you posted. But it would be helpful if the molecular ion peak could be identified so fragmentation patterns could give clues to what this compound is. (posted later: ok i see now, the spectra makes sense) I have not reviewed the literature on compounds present in mimosa but its something i have been meaning to do. also those TLC plates any idea what spray reagent was used?

basically what this all comes down to is whatever is in this red crystal stuff isn't known? at least in M. hostillis? am i missing something?

I do not endorse condone or engage in illegal activities. Talking about the chemistry and effects of various substances is just a fun thing I like to do.
 
Entropymancer
#7 Posted : 3/14/2008 2:48:06 AM

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That certainly sounds like jungle spice from the desription. It would be very interesting indeed if this person could run a GCMS of the sample. If it has been washed with heptane or something to remove the white spice, then it's unlikely the sample contains any scheduled chemicals, which is nice for whoever's running the GCMS.

With the GCMS done by Radio897, the sample had not been purified, and contained primarily N,N-DMT. The peaks for the DMT-oxide and proposed yuremamine degradation product are small enough that their fragmentation patterns are essentially indistiguishable from noise. This is obviously less than optimal, since it makes it more difficult to be certain of the proposed identities.

Detials on the TLC Analysis by Dozuki are on entheogen.com: Link 1, Link 2.
I'll include at least a brief discussion of the plates eventually. (Right now it's finals time, so this project's on hold for a week or so)

When this person runs the GCMS, I was wondering if there were any way they could get the raw data in digital form (ie an excel file or text array of pairs of m/z and abundance or something like that). As I recall from my (limited) experience running a GCMS, there wasn't an option in the program to export the data in this form, but I had no problem selecting the data and copy&pasting it into a text file. The reason that I ask is that it's easier to analyze as compared to looking at a scanned printout. If this isn't possible, it's no big deal; scanned printouts are certainly useful!

As I see it (and bear in mind I haven't finished weighing the evidence totally yet), the bottom line with respect to the red stuff is that it's most likely a compound that yuremamine breaks down to during the extreme pH conditions of the extraction process. It does not appear that it is a compound which can be found in the rootbark prior to extraction.
 
burnt
#8 Posted : 3/14/2008 8:26:47 AM
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Cool I will let you know shortly when this person does the analysis. Bottom line to me is if its active and it can be identified thats interesting, artifact of extraction or not (extreme pH is also in the gut). Also has anyone consumed this compound orally. There are reports in the ott articles that M. hostillis is orally active. Any idea about that? and good luck with finals! Wink
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burnt
#9 Posted : 3/14/2008 7:36:55 PM
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GC-FID and GC-MS main compound = spice (nothing else in GC-MS) (minor minor peaks in GC-FID). nice spectra to according to this guy who ran it. anyway based on that evidence:

1: either this is not the stuff everyone is talking about. (although it looks the same)

2: The compound degraded (this stuff sat around for a few months).

3: tannins or something similar are all thats giving this stuff its reddish color.

Many things could play a role in the different effects people say they have. Minor components in herbal extracts sometimes play bigger role then it would seem. personally i wouldnt want to smoke something with all those tannins in it. the whole reason to do an extract is one to get freebase thats smokable and two to avoid all the stuff that makes you sick (ie tannins and what have you).

Anyway its still interesting from a biosynthetic point of view the yuremamine compound. im sure within time the group who found it will work out its pharmacological profile. at least they should. anyway all they did to identify it was a methanol extract for a few weeks in the cold and evaped under nitrogen (which might not be necessary). anyway if one wanted to further purify this compound chromatography or some fancy tricks would be necessary and thats definatly not a simple kitchen task especially with an unstable compound. still really cool discovery by that group.



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Entropymancer
#10 Posted : 3/14/2008 10:12:16 PM

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Interesting.... nothing in it but spice? I'm wondering how that can be, when the red fraction was insoluble in the nonpolar solvent when white spice was pulled from the red. I could understand some trace spice left behind, but it's hard to imagine it being the primary component. Very interesting.
 
burnt
#11 Posted : 3/15/2008 9:46:18 AM
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yes it is curious because yea the whole reason this guy has some of this stuff is because it was not soluble in the hexane. but yea next time this guy winds up with some of it he will try to run it fresh. he ran both color spices just to be sure and they matched up perfectly.

anyway it could be thought of that maybe its just a solubility issue. like ok so someone extracts with toluene or ether or whatever so that brings in more of these colored components minor but none the less there. then he or she extracts from this red goo using warm hexane to get white spice. i would just think this red gunk if just a cruder extract basically.

its also curious the different subjective effects people are having. but like i said herbal extracts often have minor components that can potentiate the effects of the main active compound.
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acolon_5
#12 Posted : 3/17/2008 3:10:41 PM

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^
Why then does the ayahuasca crowd find that mimosa produces such different dreams than P. Viridis?
The Spice extends life
The Spice expands consciousness
The Spice is vital for space travel
___________________________________________________________________________________________________
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I am certifiably insane, as such all posts written by me should be regarded as utter nonsense or attempts to get attention.

I don't know SWIM and personally don't trust him at all. If SWIM is posting, most likely I will not respond...as I said, I don't trust the guy. YOU I trust, but never SWIM.
 
burnt
#13 Posted : 3/17/2008 5:35:48 PM
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well it depends on route of administration. if your talking oral if your taking p viridis mixed with b caapi youll certainly have different effect then mimosa on its own. but if your talking about extracts freebased then it could be a result of minor components. like i said herbal extracts contain many chemicals many of which do have some kind of biological activity and figuring out exactly how that works is no simple task. this is very obvious with the case of THC and cannabis. the cannabis plant contains many biologically active chemicals which are certainly doing something to modify enhance or decrease certain effects of THC. this seems to be the case with almost any herbal crude drug. plus set and setting play a role. its such a complex mix of factors and i find it utterly fascinating.
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Entropymancer
#14 Posted : 3/27/2008 12:40:02 AM

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I was looking back at the Callaway article, it looks like they used liquid-chromatography/MS to identify the yuremamine. While I'm not suggesting that yuremamine is the jungle spice, it seems like the yuremamine must break down into something during the extraction process. It doesn't make much sense that analysis in the literature has never seen this breakdown product... alkaloids don't just disappear when they degrade. So I'm thinking that maybe the main component of the jungle spice isn't amenable to GC-MS. Then again, it seems strange that something which is active when vaporized would have trouble in the GC.

I guess now the question is whether anyone can run an LC-MS on the sample.
 
burnt
#15 Posted : 3/27/2008 9:04:48 AM
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someone should replicate their extraction method in that paper first. they used a very soft extraction method with a minimal amount of plant bark. get GC-MS or LC-MS i dont think it would matter in this case except that a GC-MS method is usually easier to set up. get specta/retention for yuremamine. then compare that extract to an extract done by one of the methods seen here that seem to be giving this so called red spice. this will answer the question of whether or not yuremamine is extracted by methods done here. then the question of where did it go can be examined.

also it shouldn't be ruled out that the main compound in this red spice is regular old white spice. if you add warm hexane to these red extracts you seperate the dmt from the red stuff and can get more purer spice. this has been done. think of the toluene or diethylether pulls being good at extracting spice + other stuff. while hexane and naptha is ok at extracting mainly spice. thats why warm hexane/naptha is used to recrystallize simply because dmt although is soluble in these very non polar solvents its not that soluble. if you try to recrystallize with toluene it doesn't work as well. at least i dont think it does.

i can ask this guy i know to do it if he ever happens to have more root bark laying around.
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Entropymancer
#16 Posted : 3/27/2008 3:53:50 PM

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Actually, I'm pretty satisfied at this point that yuremamine is not present in the red spice. I think that some further TLC analysis could confirm this, but I don't see it as that high of a priority. Until I see evidence otherwise, I'm going to consider the jungle spice to be something other than yuremamine.

burnt wrote:
also it shouldn't be ruled out that the main compound in this red spice is regular old white spice.


I am certainly open to the possibility that most samples of jungle spice will probably contain some DMT that doesn't seperate from the colored fractions for whatever reason. I'm even open to the possibility that DMT composes a large percentage of the jungle spice (though in the case of heptane-washed spice, I sort of doubt it).

But what cannot be denied is that at least some extractions of jungle spice have allowed people to consistently achieve breakthrough experiences at doses of 25 to 35 mg. That means that there's something in there besides DMT. I just don't see any other way to slice it.
 
burnt
#17 Posted : 3/27/2008 5:19:20 PM
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Yes I agree theres definatly something else in it otherwise it wouldnt be red. And yes I dont think its yuremamine either. I think 1 of 2 things could be taking place. 1 the other stuff in this type of extract potentiates DMT. By effecting some other system like the blood brain barrier permeability or receptor sensitivity or something like this. Meaning there are biologically active compounds in this mixture. 2 there is another more potent 5-HT agonist present. Both are interesting possibilities. Although I think the potentiating theory is more realistic otherwise someone would have discovered this agonist because its a fairly straight forward procedure to use bioassay guided fractionation to find the most potent active compounds. What I mean is they would have discovered it when they found DMT. Whats more difficult to prove is how other compounds effect the effect of DMT. Thats the primary struggle in herbal medicine in general.

Some guy I know did a toluene pull from his last straight to base mimosa extraction after pulling with naptha like 4 or 5 times. A red oily material that seems to be hardening was present. Upon freezing this material crystals started to form within this blobby mess. My friend is fairly certain it contains dmt and well definatly contains something else. Maybe he will sample or chemically test but he is nervous to use more "impure stuff". Either way its fun to investigate these things and good to clear up some of the myths floating around the internet.
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Entropymancer
#18 Posted : 3/28/2008 2:08:49 AM

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Yep, those are pretty much the possiblities as I see it. What complicates things is the fact that both red and brown compounds have been isolated, which most certainly have different compositions, and then there's the issue of biologically active oxidation/degradation products. And we have to consider the possibility that the rootbark may be from a different Mimosa species (which would explain why it hasn't been reported in any literature)

The picture quickly becomes pretty muddled.
 
Big Inhale
#19 Posted : 3/28/2008 2:55:40 AM

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maybe its kokusaginine this was talked about in page 3 of the dark dmt-the other alkoloid thread the post is by implants
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Entropymancer
#20 Posted : 3/28/2008 3:04:57 AM

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I'm not sure I understand what you mean. I discuss the so-called "kokusaginine" in Section I.3
 
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