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Author: Subject: Dangers of possible Terpene, cannabinoid, ozone reaction & free radical formation?
Hockeydemon
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[*] posted on 28-2-2013 at 09:34
Dangers of possible Terpene, cannabinoid, ozone reaction & free radical formation?


Hey everyone,


I don't feel as if this subject is getting enough attention for it's implications and WIDE spread. People all over the world by the millions are running their own oil extractions on marijuana plants. I'm sure the vast majority of them have a middle school level understanding of chemistry also.

This subject is also over my head so I figured I'd ask some people who are smarter.. Here is what someone else wrote on the topic..

"To my eyes as an organic chemist the "budder" is nothing more than side reactions with terpenes and cannabinoids--in the form polymerizations, hydrations, oxidations, and epoxidations.

It is known that terpenes react very easily in open air--and as we all know whipping (when done in air) is nothing more than incorporating air into a medium. You can probably test this by splitting a batch of oil and whipping one in air, and using a stir bar to "whip" the other under vacuum (same temperature). You will still get some polymerizations potentially but not as likely as these typically happen with terpenes (and other alkenes) under increased, rather than reduced, pressure.

Furthermore you will have pulled proteins and amino acids out with an oil extraction, and these are known to react with oxygen containing terpenes. The list goes on an on.

Something that is important to understand is that C-C pi bonds (double bonds, but specifically the p orbitals of the "second" bond) are quite reactive--some of the most readily reacting materials on the planet excluding those which produce absolutely violent reactions (and some of these do as well). Addition reactions occur across these bonds with a litany of substances; In fact, additions across double bonds are what cause these chemicals to come to be in the first place (through many additions of isoprene units). Many times only a catalytic amount of a given impurity must be present to set off a polymerization chain reaction (not to be confused with PCR, polymerase chain reaction). Believe me when I say that I'm not overstating this.

I believe many of these terpenes actually self assemble and fold into their various odiferous forms during the curing process--this should demonstrate to you that these are reactive substances as these foldings and additions are non-enzymatic and occur spontaneously.

Furthermore, it would be expected that as you increase carbon chain length (polymerization takes care of this) and saturate carbon bonds (add across double bonds) you will expect to see oils become more opaque, and increasingly firm. This is, in fact, the precise difference between saturated fatty acids such as stearic acid (animal fat) and unsaturated fatty acids like oleic acid (olive oil).

Exposure to any of the following will more than likely lead into degradation/polymerization of terpenes through various pathways:

--Heat
--Oxidants (air)
--Acidic/basic conditions
--Free Radicals (atoms/molecules with an unpaired electron/open shell)


Even a single molecule of ozone can produce significant results with terpenes--leading into a long chain of possible side reactions.

It is almost certain that buddering is not desireable. I would more quickly smoke the butane than wonder about what chemicals I may have just produced by that process.

I'm sure you mean elaborate, and so I shall.

Polymerization is a process by which monomers (similar subunits) are linked together to form a polymer (poly meaning many and mono meaning one).

Terpenes are known to polymerize under certain conditions. Most alkenes (C-C double bond is an alkene functional group) are fairly reactive, but terpenes are made up of special monomers called isoprene, or isoprenoid, units (isoprene is short for isoterpene).

Under various conditions, not the least of which being presence of air and heat--previously stable terpenes may begin to break apart/link together in a way not dissimilar to the linking together of isoprenoid units. A polymerization of polymers if you will.

In addition to this terpenes are known to react with various compounds to give new compounds (in the case of ozone for example). Google terpenes ozone and do some digging if you want to see how complex this can get in terms of side reactions--this reaction can give a hydroxyl radical which can go on to do all types of nasty shit.

In general I'm saying stuff doesn't just change color and consistency from losing less than a mL of solvent and a little heat. A reaction is occuring.

In terms of elaborating on the possible danger/non-danger. I can't. No one really can--this stuff amounts to a chemical soup in terms of how many compounds are present. You get to doing side reactions/polymerizations in a chemical soup and you could end up with some fairly terrible results. As a for instance, adding only 3 reactants in a research lab once left me with maybe 100 different compounds at the end of a reaction where an impurity had caused side reactions to take place. The NMR looked black clear across!

Now consider that there may already be 100's of compounds present in an extract.

I'm not trying to say its certainly unsafe--but it could potentially be creating carcinogens and other nasty things. I'm ultimately saying sans a lab and lots of fancy testing we won't know or even come close to knowing. Even then this could be on a plant to plant basis in terms of deciding whether this process is safe. Each plant has different relative levels of terpenes and cannabinoids and different terpene profiles. That changes reaction conditions and confounds analysis.

This could also be a hydration reaction, as some terpenes are known to complex with water to create--I believe--a trihydrate. This would be considerably less dangerous. Testing this might be easier. Weigh a beaker (with stirrer and oil already in) on an analytical scale. Whip up a batch. Re-weigh.

There should be a noticeable difference in weight if hydration is occuring. (depending on the mechanism the same will be true for oxidation)"


Any thoughts on this? For those that are not aware cannabis oil extraction is a huge phenomenon right now, and it is so easy to do millions of people are every day.
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radagast
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[*] posted on 28-2-2013 at 17:18


If you have access to an academic organic lab and your supervisor has the appropriate DEA licenses, it'd be interesting to characterize what compounds you get from these processes, and see if any of them are known to be harmful (I suspect there's been much research done on this subject already).

That being said, I'm not familiar with the terms used here. What's "budder"? What's "whipping"? Why is the process not performed under inert gas to prevent polymerization . . . or is the polymerization desirable to form the end product?
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violet sin
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[*] posted on 28-2-2013 at 18:07


budder = cannabis "honey" oil that is more buttery/waxy than tar/honey like. suggested above as caused by polymerization.
whipping = to whip up, ex. whipped cream. oxygen free atmosphere suggested to see if it participates in said polymerization. if it was done under nitrogen it may not change consistency.

I am assuming the guy is saying that among other things like decreased potency, nasty crap that you don't want to smoke can be made by the standard BHO extraction process. I have noticed some oils turning to varnish like layers over time. like the cooking pan we use for taco shells. obviously not the same kind of oil but.. it does turn toughly adherent and in some cases pliable coatings with heat and air over time. wouldn't wanna smoke that.

seems REALLY pointless as it is still going to be set on fire(or electrically vaporized *in air*) and inhaled.... I don't think it is really going to be damaging the yields or you lungs to any greater degree than smoking an equivalent amount of leaf/bud.
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[*] posted on 28-2-2013 at 22:18


I've been wondering about these types of extractions a lot lately, especially now that it has become legal in a few U.S. states including my own. Anybody know of the legalities involved in pursuing these experiments if it's only legal on state level and not federal level?
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radagast
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[*] posted on 28-2-2013 at 22:38


This is not legal advice, but extracting the THC oil with the intent to sell, distribute, or use it for psychoactive purposes without a DEA license remains a federal crime. Thus, even if you live in a state which has legalized THC and its various analogs, that only means that the state prosecutors will not bring charges against you under state law. Federal prosecutors, however, can still come after you, and federal sentencing penalties are usually far tougher than their state equivalents.

In practice, state law enforcement generally handles most crimes, whereas the federal government has less resources and has to pick and choose its cases. So, it's questionable whether the feds would really go after a curious experimenter, especially when the AG has indicated that he's not very interested in prosecuting those cases. But, note that this is almost exactly what happened in Raich, where a woman who grew several weed plants was raided by a joint state-fed task force enforcing federal law -- even though the same action was legal under California law.
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Hockeydemon
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[*] posted on 28-2-2013 at 23:23


Lol it is probably more dangerous to have a laboratory in your house for amateur experiments than to do BHO extractions.. There are several groups of organic chemists that are doing just that though. I only know of two.. One is SkunkPharmResearch.com in Oregon.
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[*] posted on 1-3-2013 at 06:12


Add some antioxidant like ascorbic acid.



Rest In Pieces!
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jwarr
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[*] posted on 1-3-2013 at 08:05


If those reactions are so dangerous then people would have died from hashish long long ago
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[*] posted on 1-3-2013 at 08:51


It's not likely to be problem. As violet sin said, if those particular terpenes were so unstable they wouldn't survive smoking as well as they do. Extracting them out of the plant isn't going to make them super reactive all of a sudden. You're being paranoid ;)



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radagast
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[*] posted on 1-3-2013 at 14:45


Quote: Originally posted by Hockeydemon  
Lol it is probably more dangerous to have a laboratory in your house for amateur experiments than to do BHO extractions.. There are several groups of organic chemists that are doing just that though. I only know of two.. One is SkunkPharmResearch.com in Oregon.


That's probably true, because if you have a lab, people will just assume you want to make meth.

Anyway, with respect to terpene polymerization in THC, I'd think that it would be about as harmful as ingesting/smoking resin from a pinecone or a tree. That doesn't strike me as particularly harmful -- and I'm imagine that the terpenes would polymerize to a certain extent naturally without the "budding" process -- but nobody can really say for sure.
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[*] posted on 1-3-2013 at 15:30


Also on a legal stand point, here in California you can get a medical card and you can buy medicinal smokables,,, but. You can't make it (BHO)your self( felony prod. Cont. sub). Like wise you can buy it but as soon as you walk out the dispensary you can be popped if they want. I asked some LEO's and they said compressed kief or resin in small amounts is "a wobbler", ie if you fail the attitude test they grill ya. And if your not a dushe they may just leave or take the small enough amount. But I point blank asked a guy who busts people ( we grew up in the same neighborhood)and he said it is too strong and will always be illegal to produce. They were talking like it was a crazy halucinogen. Lol
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[*] posted on 3-3-2013 at 22:23


"budder" is not honey oil; it is cannabis that has been cooked in butter to extract the nonpolar components (cannabinoids are the target). When making BHO, you're basically just immersing finely ground cannabis in a lot of butane. Since butane easily vaporizes at room temperature, this eventually leaves the full-spectrum cannabinoid/terpene extract. The only oxidation I can see happening is that which occurs due to the increased surface area of the herbal matter due to grinding. Cooking herbal matter in a solvent like ethanol for extended periods of time is another matter -- I'm not sure what to say about that.
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Hockeydemon
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[*] posted on 4-3-2013 at 01:44


@Radagast: I had that same thinking except all of these chemicals are contained nice and neatly within the cell walls of the plant matter. They never have any chance in coming in contact, especially at any concentrated level. I mean there is clearly chemical reactions happening, I can watch my oil change if I leave it out exposed to the atmosphere. Even when you smoke actual plant matter the chemicals can't come in contact with one another at any high concentration, and the temperature of a lighter is pretty low usually.

Conversly.. The extract combines all of the chemicals from a large quantity of plant matter, and the oil dome set-up vaporizes the oil at around 2500F well above the temperature required for hydrogenation of the oil..


@Rich_Insane: That is a misnomer (at least where I am). 'Budder' in the context of oil refers to oxygenated oil that a person has 'whipped' much like you'd whip egg whites. This gives the oil a waxy, fluffy saturated fat consistency. Conversely if I immediately place the oil into a dessicator, and purge the oil limiting the side reactions I get an oil with the consistency of glass (i.e Shatter). I can take the same exact product and do these to steps differently to result in a completely different product. This cannot be anything else than the result of side-reactions can it?
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violet sin
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[*] posted on 4-3-2013 at 20:27


@ rich_insane: ya I am quite familiar with the processes involved with both. not bragging or trying to come off as a jerk though. budder, as I also know it, is the ear-wax color and textured version of honey oil. made by out-gas mixing BHO extractions, or result liquid CO2 extractions. could just be a coincident on the CO2 extracted though, as the only samples I have seen looked like that. doesn't mean CO2 always does that I guess.

if done right it can come out like amber glass which shatters, like amber honey that's sticky as hell, like opaque rich golden waxy paste, and like yellow powder that tacks up with heat. that's just the few I am familiar with. I think for the most part the texture is a direct physical footprint of the process. the only time you really see any change in form, is over time with exposure to ambient air like stated above. so ya oxygen is more than likely SLOWLY doing its magic. but I doubt it would only be working on the THC affecting yields. as stated above there is a lot of material that comes out with the target content, also possibly being oxidized.

experimenting can be dangerous b/c -here- one would be treated as if they were making meth!!! same sentence, same disrespect by law, same years of scrutiny!!! you have been busted for manufacturing a controlled substance and that's gonna follow you for a while. even if you have a marijuana prescription, which is kinda retarded but.. the law.
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[*] posted on 8-3-2013 at 13:45


It's an interesting legal situation here in Colorado, a personal and commercial legalization amendment passed, the legalization task force is composed of law enforcement and big money dispensaries who want to limit the commercial trade to big money dispensaries and the State is basically aiding and abetting it all and collecting medicinal sales taxes even if it is illegal under federal law. Water is the only solvent medical dispensaries can use (bubble hash), one needs an edibles license for organic solvents, a patient can presumably grow and extract.

Perhaps it's a prejudice from my time in organic chem labs, but I would prefer spectro grade analytical reagent n-pentane and glassware to butane. Particularly if I wanted to try activated charcoal filtration or a Roger Adams vacuum distillation of the red oil.

An inspector from the Colorado dept. of health and environment walks into a facility with giant heating mantle and soxhlet extractor. He pauses, looks at it and says "it doesn't smell like a meth lab" and keeps walking.
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