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NONTOXIC LIMONENE TEK

Migrated topic.
SWIM would love to learn how to distill his own limonene so he can keep doing this after society collapses in whatever apocalyptic eschaton may lie in its future. If you have a reference for how to do this, brother burnt, it would be most appreciated. Though I agree it's much easier to just order some online in the mean time.
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well the main way to obtain essential oils is by steam distillation. you can buy steam distillation apperatus's online but they are expensive. the glass ware tends to be fancy. but steam distillation was done a few hundred years ago so might be best to look into some of the other methods (they had some cool aparatus's for that kinda thing). but the principle is the same. the idea is just to heat your plant material in lightly boiling water in a vessel. the vessel is connected to a long thin tube that goes up. then you have another tube coming out of the side "condensor" which has cold water passing through it to cool the oil and the oil will fall into a collection vessel. i cant really describe it so i found some pictures.


theres also the lighter then water steam distillation apparatus that im partial too because it makes it easy to separate the water that cools from the oil because the oil sits on the water. anyway start saving your lemon peels cause you'll need a lot!

Freeze precip may work. Initial attempts at this failed, but that was back in the beginning with low-grade bark and in retrospect the limo may not have been saturated enough. However I think there's something going on here similar to whatever it is that makes freeze precip not work with toluene, xylene, etc. Something about the boiling point of the limo, methinks...
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well the reason dmt is very difficult to freeze precipitate from toluene and xylene and even limonene is because dmt is more soluble in those solvents then in hexane (or naptha or other straight chain hydrocarbons). so no matter how cold you make it the dmt is still happy to be in solution. as far as evaporating down and saturating yes some of the dmt may start to precipitate but yields wont be as high as they could be. if the limonene oxidizes or contains other components this will make it even harder. however there may be a way. i have to think more about this and consult some literature but if one could use some salts or something to render the dmt insoluble in limonene it could precipitate out.

anyway the technique is called salting out. its usually applied to salting out things in aqueous solutions. just thinking off the top of my head the salt would have dissolve in the solvent to increase the ionic strength of the solvent and causing the compound to precipitate out (this is what happens when you do it in water). so yea i dont know how this would apply with an organic solvent. it could have the opposite effect.
 
From what I saw (the early stages of the tek), some red goo formed after evap. Is there a way to evaporate it all down so that you have DMT + limonene residue, then find a way to wash out the limonene residues and leave DMT?

Surely though, this residue could be added to herb and smoked nicely, no? How well does that work?
 
whatever washes away the limonene also wash away the spice. but yes if you evaporate all the limonene you will be left with spice and whatever else the limonene extracted (probaly the same red stuff as in toluene extracts) so called jungle spice. i gotta re-read the tek though make sure im getting this all right.

if the goal is to obtain crystals we must get more fancy to get the dmt away from the limonene. if the goal is to just get a crude mixture that you can happily toke then i think you guys already got that.
 
ok sorry guys. i didnt read about the vinegar part. so basically what you are doing there is moving your spice back into the aqeuous vinegar phase and evaporating it down?

so why not just evaporate down the limonene? because you want to recycle it? ok another point if your dmt is in salt form it will be more difficult to smoke for the same reason that cocaine hydrochloride is harder to smoke then freebase cocaine. the freebases usually have lower boiling points and can be vaporized easily.

a friend of a friend of some invisible friend has access to lab grade d limonene and can check the solubility issues for you all when he has time.
 
Sorry for the slow response time, been bizzy working on a paper on harmaloids and potentiation.

Thank you all for your interest in this technique. Feels like we're really making progress here... 8)

Burnt, your help is much appreciated. Sounds like you really know your stuff, it's great that you're willing to contribute :)

So, to sum it up... the limo Swim had been using may have been pretty crude, cuz it left a LOT of residue on evap. So much that the resulting goo was not even worth smoking... more limo residue than dmt. Might as well smoke an enhanced orange peel. This may be due to the purity of the stuff Swim was using, he's found another place that sells "high purity" limonene and has ordered a sample, perhaps this will be what we're looking for.

In the mean time, yes, Swim has been salting the magick out using vine gar, to reveal acetate salts. Problem is, they don't seem to be worth smoking. They are, however, GREAT for oral ingestation with a maoi, which Swim feels is the proper use for this medicine. But he still acknowledges smokable freebase as the ultimate visionary tool, so yeah, he would love to find a way to get freebase.

Is there any way to freebase a salt once it's extracted? For instance, I know crackheads somehow freebase their hcl salts using baking soda... I think I read about someone trying this with dmt salts one time and they said it didn't work, but perhaps they just didn't know what they were doing? Would there be any way to accomplish something like this, once the acetate salts were pulled from the limo?

Burnt, if your invisible foaf is able to do get specs on pure d-limo, man, that would be awesome! Also, thanks a bunch for the limo distillation linkage! You da man!

Sinewave, as for insufflation... you may be onto something there. Swim hasn't tried it yet, but yeah, it seems the acetate salt goo could be dissolved in a bit of water or something and insufflated in a manner similar to the way in which black tar heroin is sometimes insufflated. Swim may get the balls to try this someday, if he does I'll report back.
 
Yeah, the whole limo degredation thing seems to be a problem. Even with pure stuff, assuming it evaps clean, it may oxidize into stuff that doesn't evap so well, eh? Still, Swim has yet to try evaping using heat... perhaps the limo goo that won't evap at room temp might do so at crock pot temp?

Using the tek in its current form, Swim ends up with a crude extract that is dark red (almost black) and gooey. It's kinda like mj resin (though perhaps not quite as sticky).

It is vaguely possible that if, instead of evaping the vinegar, one were to re-basify it, and re-extract into more limo, then salt out again, in a manner similar to Coschi's tek, then perhaps one could aquire a purer, more crystaline product by removing some of the oils, etc. Also the use of pure acetic acid would help if purity is a concern, since vinegar leaves some of its own white powdery residue behind after evap. But given that there's probly a lot of jungle spice in there, I wouldn't hold my breath waiting for crystals to form, since the jungle doesn't ever seem to wanna xtalize anyway. So we're basically looking for a way to freebase the goo, methinks.

Any thoughts?
 
I read here: http://www.craftsreport.com/june96/labels.html

that d-limonene is borderline toxic, it has problems with retaining pesticides from growing, and it also has a very strict air quality exposure level (PEL) of 30ppm, as compared to 300ppm in OMS or vm&p naphtha. Certainly, it's not carcinogenic, but it has shown some sketchy results in animal tests.

Citrus oil and its major component, d-limonene, are derived from the rinds of citrus fruit. We like to buy products containing these ingredients because their advertising implies that these "natural" and "biodegradable" substances are safe. Examples of products containing citrus ingredients include Citra-Solv, Lithotine, Citrus Clean, Grumtine, Citrus Turps, Fast Orange Hand Cleaner, and many paint, solvents, strippers and cleaning agents.

Advertisements for these products often emphasize that the FDA allows small amounts in food as an additive. The ads fail to mention that d-limonene is one of Mother Nature's own pesticides. She put it in the rinds to protect her fruit from insects. It kills flies efficiently enough to be registered with EPA as both an "active ingredient" and an "inert ingredient" in commercial pesticides.

d-limonene and citrus oil also can be contaminated with other pesticides from the spraying of the fruit in the orchards. EPA is currently proposing to revoke the use of citrus oil in food because it usually is contaminated with a cancer-causing pesticide called imazalil. Pesticide contamination also is a good reason to use organically grown citrus fruits when recipes call for grated rind to flavor food.

TESTS ON d-LIMONENE: The required tests to determine immediate (acute) hazards show that d-limonene is right on the borderline of being acutely toxic. This borderline status allows manufacturers to label it "nontoxic." A long-term (chronic) animal test by the National Toxicology Program found that it is not a carcinogen, but that it caused reduced survival rates and liver damage in the animals. D-limonene can be expected to be chronically toxic to humans.

WORKPLACE LIMITS: The manufacturer's Material Safety Data Sheets also may state that d-limonene is not regulated by the Occupational Safety and Health Administration (OSHA). This is not an endorsement by OSHA. There are many toxic substances for which OSHA has not set limits.

However, another important professional organization, the American Industrial Hygiene Association (AIHA), set a Workplace Environmental Exposure Level (WEEL) guide for d-limonene at 30 parts per million (ppm). WEELs are similar to OSHA permissible exposure limits (PELs). The AIHA's limit for d-limonene is even lower (more restrictive) than the PELs set by OSHA for turpentine (100ppm), vm&p naphtha (300ppm) and other very toxic solvents.

OTHER HAZARDS: d-limonene can be absorbed into the body by skin contact. Skin irritation and allergies also have been noted, especially in people previously sensitized to other "natural" solvents like turpentine and anise oil. It oxidizes on exposure to air like linseed oil, so rags containing d-limonene can spontaneously catch fire. It should be kept out of the reach of children because its fruity odor has caused children to drink it.
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However:

otes: 1) Limonene is on FDA's list of synthetic flavoring substances and adjuvants that are Generally Recognized as Safe (GRAS) (21 CFR 182.60). 2) Oxidation products of limonene that form during handling and storage, rather than limonene itself, are the mediators of irritation and sensitization. 3) Although chronic oral administration of d-limonene to rats caused kidney damage and kidney tumors in the males, this effect is thought to have no human relevance (IARC Group 3). 4) Metabolized by several hepatic enzymes (CYP2C8, CYP2C9, CYP2C18, CYP2C19, CYP3A4) to carveols (6-hydroxylation) and perillyl alcohols (7-hydroxylation), with CYP2C9 and CYP2C19 showing the greatest activities in human liver microsomes.
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That's from OSHA's site: http://www.osha.gov/dts/chemicalsampling/data/CH_249450.html

Has anyone thought of using pure turpentine (wood resin base)?
 
my hypothetical friend who has crazy ideas tried to evaporate pure d-limonene + spice and got an yellow oily mixture that smells like limonene but still obviously contains spice. check d-limonene solubility thread for details. he used heat.

It is vaguely possible that if, instead of evaping the vinegar, one were to re-basify it, and re-extract into more limo, then salt out again, in a manner similar to Coschi's tek, then perhaps one could aquire a purer, more crystaline product by removing some of the oils, etc.
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i never read this coshi tek could you provide a link?

although taking your spice and passing it into an acidic water phase rebasifying and passing it back into organic solvent phase would remove any neutral impurities it will still not solve the problem that freebase spice does not want to crystallize in d-limonene, its just too soluble under normal conditions.

so ok lets think about whats happening when you add vinegar to the d-limonene. you are basically adding an acidic aqueous solution for the ionized spice to pass into, then evaporating that down. instead of using vinegar yes try using glacial acetic acid (which is a term to describe pure acetic acid). this is recommended over hydrochloric acid or sulfuric acid because these acids are all mixed with water so you have to get rid of water (pain in the ass).

so if one adds acetic acid (dropwise) to d-limonene + spice solution the spice will fall out of solution in its ionic (salt) form. (assuming the acid doesnt start reacting with d-limoene and creating more complications) i think this would be much easier to work with then a vinegar solution. then you can easily decant off your limonene (for recycling) and let the spice salt dry out. then freebase that using typical freebasing methods (which we can speculate on which ones would be easiest in this situation).

for now someone who isnt me will ask my hypothetical friend who has d-limonene and glacial acetic acid to test this idea and see if it works.
 
in response to your post clamshavefeelingstoo.

nicotine is also one of natures "natural" pesticides. i think we must realize that natural doesn't mean safe. id have to recommend the use of a solvent like limonene over aromatic hydrocarbons like benzene and toluene because it does not form the kind of carcinogenic metabolites that benzene and toluene do (rbwoodward made a post about these issues and is correct).

however it must be stressed that limonene and all other monoterpenoids interact with cell membranes changing their properties. this is why things like tea tree oil are used as antimicrobial agents because they fuck with the membrane of microbes and it can kill them. now imagine you ingest a lot of monoterpenoids (by drinking pure essential oils) your going to start messing big time with your cell membranes. not to mention that these compounds have numerous other biological activities such as directly crossing the blood brain barrier and interacting with your brain receptors. limonene has a lot of interesting biological activity. it is reasonably safe compound to work with but dont drink it and if you inhale it for a long time it can have some negative effects.

now lets take a straight chain hydrocarbon like hexane. hexane isnt safe but its not that bad. really it takes a lot of the stuff to cause brain damage and health problems. think of someone who works at a gas station who is chronically exposed to gasoline (which is mostly octane + additives the additives are usually work then the octane but anyway) they are usually fine.

this is the same issue with all chemicals it all depends on dose.

really though if yall are safe, if you work in ventilated area your will be fine. dont be foolish and not adhere to basic chemical safety procedures. just be safe use gloves (a mask isnt going to stop these small molecules from passing though it) in a ventilated area, use a fan is you like.

imagine all the crazy chemists out there working with these kind of chemicals (and way deadlier!) all the time

we are totally sane 😉
 
Thank you, clamshavefeelingstoo, for your insights. Man that really sucks about the whole carcinogenic pesticide thing... those bastards! But yeah, while limonene certainly is not 100% harmless, it is most definately much better than the common alternatives, as one can tell simply by sticking one's nose in a bottle of both solvents and breathing deeply. It's all about remaining within safe concentrations. And of course, comparing AIHA ppm standards to OSHA's standards is essentially comparing apples and oranges, no pun intended.

Burnt, man, I can't tell you how much I appreciate your help with this. Swim has been meaning to order some glacial acetate, he has also been considering trying what Loki originally suggested in the post that inspired this tek, which is using aqueous phosphate to salt out the spice, then using calcium carbonate to precipitate the excess phosphate, which could then be filtered out, and the resulting liquid evaporated to reveal phosphate salts. This may be another option if the glacial acetate turns out to be too reactive with the limo.

So, assuming one was able to somehow aquire either acetate or phosphate salts, how would one then go about "using typical freebasing methods?" What are these methods, anyway? That seems to be the main problem, as it stands right now...
 
With regard to freebasing, what seems to be the way to go about it?

I have read reports of people trying the baking soda method, ala crack, with poor results. Ammonia was another thought, though it didn't work when Swim tried it but perhaps he did something wrong...

Swim sez he would be happy to freebase his red goo that he gets from his vinegar evaps, if'n he could just figure out how... :?
 
ok well freebasing ammonia is sometimes cleaner then using baking soda. however after creating the freebase with ammonia you often repartition your alkaloid back into a organic solvent and evaporate that to get crystals.

however after doing an initial freebase with sodium bicarbonate (baking soda) you can remove any residual baking soda by washing crystals with water.

my friends will do some more hypothetical thinking on this in the coming days/week. but now party time! woow wooo
 
Ok so what would happen if one simply added some 10% ammonia to the red goo, then let it evaporate? Or likewise, if one were to add ammonia to the vinegar right before it was finished evapping all the way, and then finish evapping it? Would this leave behind freebase spice? For that matter, would the ammonia react with the acetic acid to produce ammonium acetate? Would that be a problem? Is that why one would normally repartition the spice back to an organic solvent?

Sorry I know that's a lotta questions... no hurry answering them, I'm just glad to have someone to talk to about this who knows more than me! :d 8)
 
I would love if this tech could continue evolving.. SWIM doesnt have money to get limonene right now, so couldnt do the experiments himself... but if anybody is up for it, here´s questions that would be interesting to be answered:

So what about making the extract with glacial acetic acid, how does the evaporated dmt acetate look ?

how can one freebase a dmt acetate the best way without result to petrochemicals?

is there anything one can add to lemonene which would render dmt less soluble in it (But still soluble in alcohol), so one could pass alcohol which would suck the spice up, separate and evap the alcohol?
 
endlessness said:
I would love if this tech could continue evolving.. SWIM doesnt have money to get limonene right now, so couldnt do the experiments himself... but if anybody is up for it, here´s questions that would be interesting to be answered:

So what about making the extract with glacial acetic acid, how does the evaporated dmt acetate look ?

how can one freebase a dmt acetate the best way without result to petrochemicals?

is there anything one can add to lemonene which would render dmt less soluble in it (But still soluble in alcohol), so one could pass alcohol which would suck the spice up, separate and evap the alcohol?
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I think d-Limonene is a great solvent. It smells so nice. Mmmmm…oranges. Everyone likes the smell. The only problem is it takes forever to evaporate.

DMT acetate is a goo like most other DMT salts. The only DMT salt I know of that is not is DMT fumarate.

Most acetate salts can be made freebase by applying heat. But DMT acetate might vaporize away as soon as it freebases if you do that. I believe you can vaporize DMT acetate as is because heat will cause it to separate into freebase DMT, but I’m not sure of that.

There is no easy way to freebase DMT acetate using a base without using a toxic non-polar solvent. The problem is that nearly all acetate salts are soluble in almost all the solvents you’d be using. For example, ammonium acetate, calcium acetate, potassium acetate, and sodium acetate are all soluble in water, methanol, IPA, and ethanol. Ammonium acetate and calcium acetate are soluble in acetone, and the others probably are too. (Although Ronue claims you can freebase DMT right in water and it precipitates out after a few days. Give that a try. If that works, then that would be awesome.)


The better way to go about it is to re-salt it to a different salt using an acid that’s stronger than acetic acid, like citric acid. Citrates are not usually as soluble as acetates. If you convert it to DMT citrate by adding two parts citric acid and a little water it will free up acetic acid. You then dry it, and the acetic acid evaporates away.

Now you have pure DMT citrate as a goo. You can then freebase it easily with many different methods. For example, if you added 2 parts wet calcium hydroxide to it, mix it and then let it dry, you’ll have freebase DMT, calcium hydroxide and calcium citrate. Calcium hydroxide and calcium citrate are insoluble in IPA, but freebase DMT is. So you dissolve it in IPA, filter out the calcium hydroxide and calcium citrate, evaporate your IPA, and you have freebase DMT. The same exact thing can be done using sodium carbonate in place of calcium hydroxide.
 
69ron said:
I believe you can vaporize DMT acetate as is because heat will cause it to separate into freebase DMT, but I’m not sure of that.
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Does this mean you could smoke dmt without freebasing it? Thought everyone said that would not work.
 
Dagger said:
69ron said:
I believe you can vaporize DMT acetate as is because heat will cause it to separate into freebase DMT, but I’m not sure of that.
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Does this mean you could smoke dmt without freebasing it? Thought everyone said that would not work.
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No. You cannot easily smoke DMT hydrochloride, DMT fumarate, etc. This would only apply to DMT acetate. Acetates are unstable and tend to come apart in the presence of heat forming acetic acid and the freebase alkaloid. For example, harmaline acetate, when dried with heat forms freebase harmaline and acetic acid. But harmaline hydrochloride, when died with heat, just forms dry harmaline chydrochloride.

So, this will work with harmaline. You can smoke harmaline acetate and it will convert to freebase harmaline as it's being smoked. The same is probably true for DMT acetate, but I don't know of anyone who's tried it.
 
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