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Author: Subject: cannabidiol to tetrahydrocannabinol
Assured Fish
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[*] posted on 15-4-2019 at 21:36



Quote:

there will be mono, di and even tri acetyl codeine.

What?
Triacetyl codeine is impossible, there is only one other location for codeine or morphine to be acetylated and that is the amine which is still impossible.
Unless you are proposing that the monohydrofuran can somehow be cleaved prior to glucuronidation.

I also find it irrepressibly illogical to assume that the presence of these certain analogous compounds would assert a location of production.
Acetylation of morphine is a straight forward reaction which essentially consists of lightly refluxing acetic anhydride with morphine freebase.
This procedure is unlikely to change much from one manufacturer to another, meaning the concentration of unreacted and partially reacted product WILL NOT change depending on region.

What i suspect the DEA analytical chemists actually do, is analyse the other impurities such as the presence of certain alkaloids which may help the chemists determine from which plant the original opiate alkaloid came from.

However given that all 3 of species of poppy that are commonly used to produce opiates can be grown and are grown in virtually every part of the world to some extent (even the the frozen wastes of new zealand). It is still irresponsibly illogically to assert that "Oh this heroin contain alot of thebaine therefore it must have come from Iran".

I apologize for somewhat derailing a thread but i will not suffer a lie to live.




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[*] posted on 16-4-2019 at 03:41


No such thing as Tri acetyl morphine
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[*] posted on 16-4-2019 at 05:11


Quote: Originally posted by S.C. Wack  
Quote: Originally posted by Nitrous2000  
In fact, diacetyl morphine is easy to make.

Not with acetic acid.


Quite right. Acetic Anhydride is tough to get.... but the theory is that the mono acetyl morphine is created in vivo or more likely vitro during the process of testing.
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[*] posted on 16-4-2019 at 07:54


Quote: Originally posted by Assured Fish  

Quote:

there will be mono, di and even tri acetyl codeine.

What?
Triacetyl codeine is impossible, there is only one other location for codeine or morphine to be acetylated and that is the amine which is still impossible.
Unless you are proposing that the monohydrofuran can somehow be cleaved prior to glucuronidation.

I also find it irrepressibly illogical to assume that the presence of these certain analogous compounds would assert a location of production.

you might take at look at this article. Again, I don't want to get into a debate at the curly arrows level of chemistry. :)

https://pubs.rsc.org/-/content/articlelanding/1926/jr/jr9262... An oldie to say the least
Acetylation of morphine is a straight forward reaction which essentially consists of lightly refluxing acetic anhydride with morphine freebase.
This procedure is unlikely to change much from one manufacturer to another, meaning the concentration of unreacted and partially reacted product WILL NOT change depending on region.

What i suspect the DEA analytical chemists actually do, is analyse the other impurities such as the presence of certain alkaloids which may help the chemists determine from which plant the original opiate alkaloid came from.

However given that all 3 of species of poppy that are commonly used to produce opiates can be grown and are grown in virtually every part of the world to some extent (even the the frozen wastes of new zealand). It is still irresponsibly illogically to assert that "Oh this heroin contain alot of thebaine therefore it must have come from Iran".

I apologize for somewhat derailing a thread but i will not suffer a lie to live.


Hey guys,
I was a physical chemist so am not dumb enough to challenge a knowledgeable organic/medicinal chemists observations. That being said, the DEA have long used fingerprinting techniques to suggest drug origins. Obviously not bullet proof, but a medicinal lab manufacturing heroin would start with 'pure' (within allowable tolerances) morphine and so the end product can easily be controlled for. On the other hand, certain clandestine labs use precursors that are much less than pure. It is generally the distribution of acetylated products and their proportions that "identify" the lab. Apparently, they (?think) are pretty good at tracing it back.

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[*] posted on 16-4-2019 at 21:22



Quote:

I was a physical chemist so am not dumb enough to challenge a knowledgeable organic/medicinal chemists observations

Why not?
Worst case scenario they correct you thoroughly and you learn something.

Look, I cannot be certain if i am completely wrong or if you are just portraying the information incorrectly, you've not offered much reference nor have you specified where you came across such information.
Ive no doubt the DEA use drug fingerprinting to identify certain manufacturers to an extend, the issue i have is over the details regarding how partially acetylated impurities alone could in any way identify a region of manufacture.

Think about this logically, some dude in chile mixing some opium resin with some acetic anhydride and refluxing it in a makeshift steel pot with condenser, compared to some old guy in the mountainous region of iraq mixing some opium resin with some acetic anhydride and refluxing this in a steel pot with a copper coil condenser, compared to some hobo dude in an abandoned supermarket in Kentucky refluxing some opium resin with some acetic anhydride in a stolen round bottom flask with a stolen liebig condenser, compared to a big pharma company refluxing some acetic anhydride with some relatively pure morphing extract in a large steel vat.

Three out of four of these people were carrying out the same reaction under the same conditions, the rate of acetylation would only be determined if perhaps one of these guys were being a cheap skate and decided not to use an excess of acetic anhydride or if there acetic anhydride was partially hydrolyzed.
There are just far too many variables for any of these individuals to make an exact acetylated ratio of product with any consistency.
If the DEA were using this with the expectation of any level of accuracy then there is something very wrong with the way those chemists are conducting their science.

My advice to you would be to go back to where ever or whome ever you acquired his information from and get an exact level of detail with regard to how they actually use drug finger printing.
If this is too much to ask of yourself then by all mean bring them/it to me and i will nitpick my way through the information until i have a clear and concise answer.




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[*] posted on 17-4-2019 at 04:49


Quote: Originally posted by Assured Fish  

Quote:

I was a physical chemist so am not dumb enough to challenge a knowledgeable organic/medicinal chemists observations

Why not?
Worst case scenario they correct you thoroughly and you learn something.

Look, I cannot be certain if i am completely wrong or if you are just portraying the information incorrectly, you've not offered much reference nor have you specified where you came across such information.
Ive no doubt the DEA use drug fingerprinting to identify certain manufacturers to an extend, the issue i have is over the details regarding how partially acetylated impurities alone could in any way identify a region of manufacture.

Think about this logically, some dude in chile mixing some opium resin with some acetic anhydride and refluxing it in a makeshift steel pot with condenser, compared to some old guy in the mountainous region of iraq mixing some opium resin with some acetic anhydride and refluxing this in a steel pot with a copper coil condenser, compared to some hobo dude in an abandoned supermarket in Kentucky refluxing some opium resin with some acetic anhydride in a stolen round bottom flask with a stolen liebig condenser, compared to a big pharma company refluxing some acetic anhydride with some relatively pure morphing extract in a large steel vat.

Three out of four of these people were carrying out the same reaction under the same conditions, the rate of acetylation would only be determined if perhaps one of these guys were being a cheap skate and decided not to use an excess of acetic anhydride or if there acetic anhydride was partially hydrolyzed.
There are just far too many variables for any of these individuals to make an exact acetylated ratio of product with any consistency.
If the DEA were using this with the expectation of any level of accuracy then there is something very wrong with the way those chemists are conducting their science.

My advice to you would be to go back to where ever or whome ever you acquired his information from and get an exact level of detail with regard to how they actually use drug finger printing.
If this is too much to ask of yourself then by all mean bring them/it to me and i will nitpick my way through the information until i have a clear and concise answer.


Thanks for your feedback - and the offer. I might put it on my to do list, but right now, my pressing issue relates to CBD and THC. Ultimately, we may simply to a limited assessment of vaporized CBD with pre vape and post anaylsis. What we know for sure is that depending on the source, CBD oils often contain waxes that, when used as a tincture or edible is benign, but when inhaled, there is a lipoid pneumonia like illness that is described as a "Tree in bloom" CXR.

Again, if I have the opportunity to pick a knowledgeable persons brain on the acetylation / fingerprinting technique, i'll go for it. But I should say in advance, that when disciplines cross, a P Chem is only a bit above useless when conversing with pure sciences ie analytical / forensic chem. That being said, we can be helpful with interesting observations hence the morphine/hydromorphone paper! :)
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[*] posted on 17-4-2019 at 16:12


By the way: if being called a "wanna be" kid who has no idea which end is up.... is the standard way your forum responds to questions.... you shouldn't be surprised that folk would be reluctant in posting any serious question on this forum. That will be your loss, of course since there are many who have unique information that many would find useful. just an observation
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[*] posted on 17-4-2019 at 16:43


Quote: Originally posted by Nitrous2000  
By the way: if being called a "wanna be" kid who has no idea which end is up.... is the standard way your forum responds to questions.... you shouldn't be surprised that folk would be reluctant in posting any serious question on this forum. That will be your loss, of course since there are many who have unique information that many would find useful. just an observation

I am not sure what comment was made that offends you.
A second read of this thread and it seems that everyone has been pretty civil and have responded to your questions properly: challenging some points and engaging with the propositions you have made. No one has called you a "wanna-be kid". In fact, Assured Fish encouraged you to challenge others even outside of your area of expertise:
Quote: Originally posted by Assured Fish  

Quote:

I was a physical chemist so am not dumb enough to challenge a knowledgeable organic/medicinal chemists observations

Why not?
Worst case scenario they correct you thoroughly and you learn something.



Drug-related discussion (which this clearly is, althoiugh the legality differs from place to place) is allowed here if the focus is the underlying chemistry (which is also the case here.) In this context you should expect some vigorous discussion of details and claims. But no one has been unkind.

[/modding]




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[*] posted on 20-4-2019 at 19:05


Quote: Originally posted by draculic acid69  
No such thing as Tri acetyl morphine

Google this and you'll find there is.

BTW part of the "so on and on" is that even if you have a statement of analytically pure CBD, that was true at one point, what happened to the CBD after the sample was taken? If it was exposed to light (10 min. of Hg light can convert it to 15% THC) or stored or mixed with something it's no longer pure CBD, and one should not expect the reactions of pure CBD from it.

PS: alt reason for 6-MAM in those prescribed morphine: homebake

[Edited on 21-4-2019 by S.C. Wack]




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Assured Fish
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[*] posted on 20-4-2019 at 23:59



Quote:

Google this and you'll find there is.

I tried this before mentioning that there is no such thing, i suspect draculic acid did the same thing.
So unless you can provide reference, then it does not exist.

It should be noted that ive also found this:

Quote:

In recent research, orally administered cannabidiol (CBD) showed a relatively high incidence of somnolence in a pediatric population. Previous work has suggested that when CBD is exposed to an acidic environment, it degrades to Δ9-tetrahydrocannabinol (THC) and other psychoactive cannabinoids. To gain a better understanding of quantitative exposure, we completed an in vitro study by evaluating the formation of psychoactive cannabinoids when CBD is exposed to simulated gastric fluid (SGF).


https://www.liebertpub.com/doi/full/10.1089/can.2015.0004




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[*] posted on 21-4-2019 at 07:21


There is a difference between existing and actually existing...it's true that it's not clear what N-acetylation could be, the oldest references pre-date full knowledge of the molecule and one of the hits Bentley says so. I was swayed by a couple modern forensic hits including a GC/MS peak assignment and a mw of 397...this is actually triacetylnormorphine and no there isn't a triacetylmorphine.

The CBD in the simulated stomach reference is semifamous for not translating when actually fed to people...there was later follow-up research.


[Edited on 21-4-2019 by S.C. Wack]




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[*] posted on 21-4-2019 at 14:13


Quote: Originally posted by S.C. Wack  
There is a difference between existing and actually existing...it's true that it's not clear what N-acetylation could be, the oldest references pre-date full knowledge of the molecule and one of the hits Bentley says so. I was swayed by a couple modern forensic hits including a GC/MS peak assignment and a mw of 397...this is actually triacetylnormorphine and no there isn't a triacetylmorphine.

[Edited on 21-4-2019 by S.C. Wack]


I googled triacetylnormorphine and you are correct that this material exists, however its not a weird quaternary amine as i would have guessed.
This book is what lead me to discover the work of a father and son on what was named the Polonovski rearrangement.
https://books.google.co.nz/books?id=wy2MV11PodsC&pg=PA26...

It appears possible for tertiary N-oxides to undergo a rearrangement with acetic anhydride wherein one of the alkyl groups is cleaved and the amine is acetylated.
https://onlinelibrary.wiley.com/doi/10.1002/0471264180.or039...
It could be possible for a small portion of the morphine to have undergone partial oxidation from the atmosphere and then undergone this rearrangement.
N-oxides probably wouldn't normally form via oxidation from atmospheric oxygen in any appreciable amount, but given how small of an impurity they seem to be talking about here, a very tiny amount may lead to these rather minuscule impurities.


Quote:

The CBD in the simulated stomach reference is semifamous for not translating when actually fed to people...there was later follow-up research.

Again you've given no reference, even if it has a past of being unreliable there is still a past there which would seem to indicate it has occurred and can occur under the right circumstances.
This might be what the OP has come across in his research, it may not be reproducible with reliability but it would still occur some of the time and enough to cause a positive test for THC in some subjects.




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[*] posted on 21-4-2019 at 14:40


Vol 2 of the same journal begins with a reply along the lines of

Bioconversion of CBD to THC, if it occurred in fact in humans, would be easily documented through increased serum levels of THC or 11-OH-THC. This has never been demonstrated. To the contrary, available evidence would support no such effect. The plasma sample of 14 patients with Huntington disease, who received CBD (10 mg/kg/day) during 6 weeks showed that no THC was detected in the plasma sample of any patients at any time during the trial. More recently, 16 health volunteers received THC (10 mg), CBD (600 mg), and placebo in separated sessions and the plasma level of THC, 11-OH-THC, and THCCOOH were elevated at 1–3 h after THC administration, but not of CBD and placebo.

The overall available scientific data, and the serum level data suggests that oral administration of CBD is a safe and easy way to use CBD, even at high doses, in a therapeutic context with no indication of human bioconversion of CBD to THC.

...again I ask, why would anyone smoke CBD? People smoke things to get high or because they're addicted.

[Edited on 21-4-2019 by S.C. Wack]




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[*] posted on 22-4-2019 at 14:23


I remember reading a paper dealing with the total synthesis of cannabinoids many years ago, and I recall that CBD easily undergoes isomerization to 6-THC (aka 8-THC) in the presence of strong acids such as p-TSA via addition of the -OH hydrogen to the neighboring alkene. There is no dehydration required. The reaction happens at room temperature in the presence of a catalyst. 8-THC is supposedly less psychoactive than 9-THC, but this is not an area I'm very knowledgeable of. I recall there being a way to convert 8-THC into 9-THC but it was a lengthy multistep process involving expensive and dangerous reagents. Since the reaction is a mere addition reaction, I imagine it is almost certain it could happen at a high enough temperature without a catalyst (perhaps to either isomer). I imagine even light/UV stimulation would cause the conversion. It's very common for such acid catalyzed intramolecular additions to take place without a catalyst at higher temperatures, so it would not be surprising.

Worth noting the reaction only occurs around a strong acid. Weak acids like citric acid have no effect. Maybe it is possible HCl in stomach acid could cause some degree of conversion, but it'd probably be very minimal due to its dilute nature.
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[*] posted on 24-4-2019 at 01:00


N,acetyl,3,6diacetylmorphine is possible.you got a technicality on that one.when we said triacetyl morphine can't exist we were referring to a triacetyl ester as anyone would have assumed,bringing nitrogen substitution into it is a bit of a non-issue as an acetyl on the nitrogen makes it an amide right?Carboxylic substitution on the nitrogen probably ma kes it inactive.theres probably a reason it's been unheard of until now like it's so useless of a compound it was made once and tested then binned.how much literature have you seen on this compound?next to none I'd bet.just because it can exist doesn't mean it does.
As far as the morphine providing a positive result for 6mam wasn't it found they were consuming aspirin with it and it was a metabolic cause of this combination.i guess like cocaine and ethanol producing cocaethylene metabolites.alcohols and acids in your system esterifying.

[Edited on 24-4-2019 by draculic acid69]

[Edited on 24-4-2019 by draculic acid69]
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[*] posted on 25-4-2019 at 03:49


CBD is short for cannabidiol. CBD is one of the main cannabinoids which are found in the cannabis plant. Medical marijuana and cannabis research is going through a period of rapid growth around the world. Many governments and pharmaceutical companies are looking into the health benefits associated with cannabis and how CBD could help with many different health conditions.
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[*] posted on 25-4-2019 at 04:35


About time they did that.80yrs of saying that something is evil and banning it worldwide has not done anyone anygood anywhere ever.all it did was hold research,devolopment,and medicine back while company's continued to deforest the world for paper grain and fibers that could have been substituted with hemp and pot.
Only now has hemp been made a legal crop to grow without being licensed and regulated into unprofitability or being branded a drug grower by the government despite the hemp not being smokeable or containing any THC.what kind of a bullshit joke is that.seriously.really were only now coming out of the dark ages.
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[*] posted on 27-4-2019 at 11:44


Quote: Originally posted by S.C. Wack  
...again I ask, why would anyone smoke CBD?


Now I understand...a smoked form is not a food or dietary supplement.

Quote: Originally posted by Sidmadra  
I recall there being a way to convert 8-THC into 9-THC but it was a lengthy multistep process involving expensive and dangerous reagents.


The addition and subtraction of HCl yield well and potassium is more available now, it would be no challenge at all. It would still be easier to irradiate CBD for 10 min...BF3.O(C2H5)2 is the one that goes at room temp, and also gives the desired isomer, and is the best choice. The tosic reaction is typically refluxing in benzene.

[Edited on 27-4-2019 by S.C. Wack]




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[*] posted on 3-5-2019 at 14:09


Quote: Originally posted by j_sum1  
Quote: Originally posted by Nitrous2000  
By the way: if being called a "wanna be" kid who has no idea which end is up.... is the standard way your forum responds to questions.... you shouldn't be surprised that folk would be reluctant in posting any serious question on this forum. That will be your loss, of course since there are many who have unique information that many would find useful. just an observation

I am not sure what comment was made that offends you.
A second read of this thread and it seems that everyone has been pretty civil and have responded to your questions properly: challenging some points and engaging with the propositions you have made. No one has called you a "wanna-be kid". In fact, Assured Fish encouraged you to challenge others even outside of your area of expertise:
Quote: Originally posted by Assured Fish  

Quote:

I was a physical chemist so am not dumb enough to challenge a knowledgeable organic/medicinal chemists observations

Why not?
Worst case scenario they correct you thoroughly and you learn something.



Drug-related discussion (which this clearly is, although the legality differs from place to place) is allowed here if the focus is the underlying chemistry (which is also the case here.) In this context you should expect some vigorous discussion of details and claims. But no one has been unkind.

[/modding]


Seriously? do you think the bong reference or the absolutely off topic solvent was 'kind'? you need to take a couple minutes to rethink this. Of course, this might be how far your group is interested in going.... if that's the case.... so be it... honestly, I don't care if most everyone on her thinks that this is a 'wanna be' high school kid asking a question.... but I'm interested to see if any of your members can see through that, and actually think about the quest(ion. I've been around way too long, and spent too many years in school for that kind of nonsense.

The question I asked it actually more complex than I had thought. Seems that the derivativization process (for sample testing) can, in itself change the results obtained. So... LC tandem MS might result in completely different result from GC / MS or similar... all due to sample prep. "Simple dilute and shoot" may well provide completely different results from those obtained by alternate methods ( and they might well be correct!) . I suspect some of you can see the implications of this.

So, is the sample ACTUALLY pure CBD as advertised or is there a significant quantity of THC contained therein? Is the presumptive test (by immunoassay) cross reactive with CBD or only THC and it's direct derivatives.... all are important questions to ask.


Interesting stuff, no?
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[*] posted on 5-5-2019 at 07:41


You do little to help your case. The only way to find answers is the obvious experiment which I proposed. Especially if one is going to go as far as artifacts of analysis (e.g. the unexpected and sometimes natural conversion of THC to CBN and both hexahydrocannabinols), it's crucial that CBD is smoked on the chosen matrix, not only because of the effects of burning with it, but because the metabolites and their reactions will also be different than oral routes.

Quote: Originally posted by S.C. Wack  
Now I understand...a smoked form is not a food or dietary supplement.


Or cosmetic, regulated at the state level.




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[*] posted on 5-5-2019 at 08:36



Why not?
Worst case scenario they correct you thoroughly and you learn something.

No, the worst thing that might happen is someone spins out BS. Such as I got from the original couple responses.... but I did learn what I needed to know, so thank you.
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[*] posted on 5-5-2019 at 11:48


Well, I tried using a very low concentration of HCl in EtOH on short reflux and it give a strong and active product(less than half of it will be delta 9 after two hours), opposed to using tosic acid, which will give almost complete conversion to delta 8, but while active, it is not very strong.
The therapeutic effects of the latter are very great though, much better than cannabidiol itself.
I would prefer the latter, the former makes me somewhat paranoid(but so does the natural product).
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[*] posted on 5-5-2019 at 13:41


Quote: Originally posted by karlos³  
Well, I tried using a very low concentration of HCl in EtOH on short reflux and it give a strong and active product(less than half of it will be delta 9 after two hours), opposed to using tosic acid, which will give almost complete conversion to delta 8, but while active, it is not very strong.
The therapeutic effects of the latter are very great though, much better than cannabidiol itself.
I would prefer the latter, the former makes me somewhat paranoid(but so does the natural product).


interestingly, if the samples are analyzed using "dilute and shoot" ie LC-MS/MS, the results are much more likely to be "derivitization artifact free' than saying GC studies which involve significant derivitization that may produce analytes that really were never there! This has enormous potential risk in regulated testing that some times believes they know more than they do!

(trouble with this group is there are a few members who genuinely want to consider and opine on an interesting subject... and others that are more interested in hearing their own voices.... each knows who they are! making it hard not to respond to some of the more enlightened response! :) )


Thanks for that.... there certainly is some evidence that stomach contents simulation will convert CBD to THC.... the clinical implications related to impairment may be far less significant than it's ability to adversely affect drug testing results.

https://www.projectcbd.org/gut-check-does-cbd-change-thc-sto...

that being said, the field of study remains incredibly nuanced... not the least of which is the persistent Federal Schedule 1 listing of this group of molecules. The DEA puts out 'regulatory patches' that are supposed to clarify things... but really they only confound issues

Thanks for your efforts. It may well be a talented civilian chemist who produces results someone with more resources (and potential peer reviewed credibility) can confirm. That is the way this war on drugs will be replaced by science and not religious hopes and fears.

[Edited on 5-5-2019 by Nitrous2000]
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[*] posted on 6-5-2019 at 08:50


As for "being active"... I vaporised the outcome, just for your information :)
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