Sciencemadness Discussion Board

cannabidiol to tetrahydrocannabinol

Nitrous2000 - 11-4-2019 at 13:40

Hi Guys,

This is not a "how to convert one legal substance to another illegal substance" thread. The question is "can the heat associated with combustion lead to conversion of CBD to THC?

There has been a study that looked at simulated stomach contents as a possible way of conversion, but while theoretically possible, doesn't seem to be an issue. This is actually a Urine Drug Testing question.... to explain positive THC (including confirmation by the THC-COOH analyte) UDT results in known to be pure CBD products.

Thoughts?
Doug

SWIM - 11-4-2019 at 16:23

Maybe if your bong has methylene chloride and paratoluenesulphonic acid in it?


Nitrous2000 - 11-4-2019 at 16:26

well, not exactly on point, or helpful but if there are comments that might be useful, please advise

draculic acid69 - 11-4-2019 at 17:00

Doesn't cbd extract come from hemp which has very low level of THC not no THC thus explaining the THC result?

S.C. Wack - 11-4-2019 at 17:30

It may be a long wait since you reject answers you don't like. Pure CBD you say...but it looks like there is nothing you can show us that will convince anyone of the truth of it.

Are you sure you have the facts straight? Why would anyone smoke CBD? If someone smoked CBD, would they be using a device previously used for THC, or a CBD-dedicated unit? Was CBD tested by eating and taking the same drug tests? And so on and on. This feels like hundreds of other threads in this way.

Assured Fish - 11-4-2019 at 22:09

In theory it could be possible to carry out an intramolecular dehydration catalysed by H2SO4 at elevated temperature (140*C i think), this is used in the production of symetrical ethers such as diethyl ether, however i believe i recall there being an exception to the symetrical rule with regards to isobutylenes which is why tert butyl ethers are used for protection of alcohols.

Now the general rule with this is that elimination takes place at higher temperatures instead but given that the alcohol is phenolic, i dont think this should happen in this case.
The obvious issue is that neither your bong or stomach would be able to produce the conditions required for such an alkylation to take place, unless we are missing something and the reaction in question is somewhat helped along by the very heavily activated ring of the cannabidiol.

This is all kinda worthless conjecture with little evidence so i think it would be far more plausible for the dumb asses who did the urine tests to have not realized that both CBD and THC undergo the same metabolic bathway leading to oxydation of that methyl group to a carboxylic acid.
So what the test actually tested positively for was CBD-COOH not THC-COOH.

slide_21.jpg - 88kB

Herr Haber - 12-4-2019 at 04:24

Quote: Originally posted by S.C. Wack  
It may be a long wait since you reject answers you don't like.

You mean answers like this one ?
Quote: Originally posted by SWIM  
Maybe if your bong has methylene chloride and paratoluenesulphonic acid in it?

Most bong owners only use solvents such as dihydrogen monoxyde or triglycerides. Some of them also use sodium chloride for its abrasive properties.

Quote: Originally posted by S.C. Wack  

Why would anyone smoke CBD?

Well if you dont know maybe it's a bit early to be this agressive ?
CBD is being looked into to replace benzodiazepines, opiates, antiemetics without the associated effects of these medicines.
This by itself is a good reason to research the compound.

Quote: Originally posted by S.C. Wack  

And so on and on. This feels like hundreds of other threads in this way.

Not to me though the question maybe wasnt clear enough.
The metabolite lead that Assured Fish suggest is probably the answer to what OP had in mind.

Nitrous2000 - 12-4-2019 at 06:07

sheesh guys,

not really trying to troll here... but i'm actually a clinician who specializes in drug toxicology. So, any reference to a bong is not helpful to me. The detailed response by Assured Fish is helpful and consistent with the literature looking at acid exposure in the GI track 'possibly' converting CBD to THC. The response by S Wack - not so much.

leaving all distraction off the basic question: can pure CBD (as evidenced by certificate of analysis) convert to THC when subjected to heat.

To Assured Fish. The CBDA would, i imagine fragment differently than THCA in tandem MS. Since the standard forensically is to do presumptive (screening) on the entire cannabinoid spectrum but definitive (confirm) testing is done only on THCA.

Anyone wanting to have a clinical/scientific discussion on THC/CBD in medical use are welcome to pose questions but "can I get high" won't be discussed. "is it psychoactive?" will be...

Thanks

Nitrous2000 - 12-4-2019 at 10:30

Quote: Originally posted by draculic acid69  
Doesn't cbd extract come from hemp which has very low level of THC not no THC thus explaining the THC result?


just for the record, Hemp is more of a legal designation. A sativa plant with less than 0.3% THC is considered hemp, for DEA purposes, and is typically cultivated for fiber. It is legal and not subject to Federal Schedule 1 status.

There is no comment on other cannabinoids ie CBD.

As far as "trace THC" in "pure" CDB oil, I'm talking about CBD that has been certified as THC free.... ie has a certificate of analysis confirming what actually is in it.



[Edited on 12-4-2019 by Nitrous2000]

hissingnoise - 12-4-2019 at 11:32

Quote:
The question is "can the heat associated with combustion lead to conversion of CBD to THC?

The answer, IMO, would have to be no ─ and it's something that would be noticed, should it occur...

I've smoked high THC and high CBD varieties over the years and their effects, taste and aroma are always somewhat different.


Fulmen - 12-4-2019 at 12:11

I have to agree with Hissingnoise, any significant conversion would have been noticed by now. But these tests can be exceedingly sensitive, so it's possible that enough could be converted for it to register (without causing intoxication). IIRC the major metabolites are different for CBD and THC, but I don't know what the UDT actually tests for.

I do know that heat and acid works, don't recall the paper that described it but a qualitative test (nudge, nudge, wink, wink) confirmed it. A milliliter or so of commercial CBD extract, a drop of sulfuric acid (perhaps 50% or so) and a bit of heat before neutralizing it with sodium carbonate.

Nitrous2000 - 12-4-2019 at 12:40

Quote: Originally posted by Fulmen  
I have to agree with Hissingnoise, any significant conversion would have been noticed by now. But these tests can be exceedingly sensitive, so it's possible that enough could be converted for it to register (without causing intoxication). IIRC the major metabolites are different for CBD and THC, but I don't know what the UDT actually tests for.

I do know that heat and acid works, don't recall the paper that described it but a qualitative test (nudge, nudge, wink, wink) confirmed it. A milliliter or so of commercial CBD extract, a drop of sulfuric acid (perhaps 50% or so) and a bit of heat before neutralizing it with sodium carbonate.


actually, the confirmatory analyte is THCA. none other. The paper you might be referring to is a case of simulated gastric contents and CBD conversion. in vivo conditions, no conversion is the practical outcome. My hope was that a theoretical potential could be tested in the lab. Looks like we may simply do the test ourselves. Thanks for your feedback.

Jackson - 12-4-2019 at 12:57

If Acid is enough to cause conversion, could stomach acid be enough?

Nitrous2000 - 12-4-2019 at 13:03

Quote: Originally posted by Jackson  
If Acid is enough to cause conversion, could stomach acid be enough?


often the difference between in vivo and in vitro....

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5744690/

S.C. Wack - 12-4-2019 at 13:10

How was the purity of this pure CBD determined? GC?

Explanation of my and SWIM's posts might be met with blank stares by those who need it.

What are the sales figures for nicotine-free cigarettes? Maybe clove cigarettes are still smoked by someone...do the kids smoke aspirin too?

Nitrous2000 - 12-4-2019 at 15:41

Quote: Originally posted by S.C. Wack  
How was the purity of this pure CBD determined? GC?

Explanation of my and SWIM's posts might be met with blank stares by those who need it.

What are the sales figures for nicotine-free cigarettes? Maybe clove cigarettes are still smoked by someone...do the kids smoke aspirin too?


might have been mistaken. Sorry. If you (or SWIM) have any reasonable process using what was originally suggested to cause that ring closure from CBD to THC, I apologize. Otherwise, I'll assume you were speaking out of your arse - with no desire to contribute to the OP's question.

For the record, the assays are done using LC- tandem MS. nicotine free cigs, are in the industry typically referred to as herbal cigarettes. My guess is what you know about cannabinoids is at best, as a personal user.

[Edited on 12-4-2019 by Nitrous2000]

S.C. Wack - 13-4-2019 at 05:02

It's as obvious now as it was before that many things are if not hidden, not clear, particularly in the absence of conclusive examination. A more interesting question is what if some analysts have said yes, but do so in such a way that it's not a particularly convincing defense of a positive UA, and other analysts say no?

Nitrous2000 - 13-4-2019 at 06:38

Quote: Originally posted by S.C. Wack  
It's as obvious now as it was before that many things are if not hidden, not clear, particularly in the absence of conclusive examination. A more interesting question is what if some analysts have said yes, but do so in such a way that it's not a particularly convincing defense of a positive UA, and other analysts say no?


That is always a challenge for a clinician advocating for the donor. As an example, the presence of 6-MAM in a sample was considered definitive evidence of heroin use... no if's, and's or but's. Except.... we have found a group of older pain patients being prescribed morphine who are also turning up with 6-mam positive reports. One question is in vivo or in vitro acetylation. Are these older men with heart disease we're giving low dose aspirin to? no pattern identified and frankly, a reluctance to try to hard to sort this out as it will make the MRO system of drug testing even more questionable in the context of opioids.

two similar (but now sorted out anomalies) UDT examples come to mind. The first is finding hydromorphone in trace amounts in morphine users and in finding hydromorphone up to 10-12% in codeine users. These have been published but the widespread use of urine drug tests in pain management has left many unanswered questions.

S.C. Wack - 13-4-2019 at 08:10

It is said 6-MAM can be made with just acetic acid and morphine, i.e. monoacetylation is easy. Unlike morphine IMHO if you want proof you'll have to smoke CBD yourself, preferentially with other subjects. It can be said for certain that 99% of the studies on the effects of CBD do not involve combustion or vapor, and what is known about the safety of smoking CBD is based on hashish, so it's possible that different CBD products produced at different temperatures and atmospheres have bad effects without THC or some other component, and smoking it is not wise.

SWIM - 14-4-2019 at 09:06

Quote: Originally posted by Nitrous2000  




If you (or SWIM) have any reasonable process using what was originally suggested to cause that ring closure from CBD to THC, I apologize. Otherwise, I'll assume you were speaking out of your arse - with no desire to contribute to the OP's question.

[Edited on 12-4-2019 by Nitrous2000]


Few things more pathetic than when a child trying to pose as a professional tries to sound 'all grown up' by referring to himself in the third person.

I'm sure the OP would agree with that. If he wasn't a child trying to sound, 'all grown up'.

Obviously, you're talking out of your ass since you haven't bothered to check the literature in any meaningful way.
The potential for conversion of CBD to THC during smoking using some traditional smoking practices was examined before you were in diapers. I realize that's only about 12 to 14 year ago, but it actually dates decades farther back than that

Try cracking a book once in a while.

And no, I won't tell you what, or where.

You're the clinical professional with the pompous attitude, so you must be such an ultrasupergenius that doing it yourself should be a snap.

Have a nice day, kid.










Nitrous2000 - 14-4-2019 at 10:09

Quote: Originally posted by SWIM  
Quote: Originally posted by Nitrous2000  




If you (or SWIM) have any reasonable process using what was originally suggested to cause that ring closure from CBD to THC, I apologize. Otherwise, I'll assume you were speaking out of your arse - with no desire to contribute to the OP's question.

[Edited on 12-4-2019 by Nitrous2000]


Few things more pathetic than when a child trying to pose as a professional tries to sound 'all grown up' by referring to himself in the third person.

I'm sure the OP would agree with that. If he wasn't a child trying to sound, 'all grown up'.

Obviously, you're talking out of your ass since you haven't bothered to check the literature in any meaningful way.
The potential for conversion of CBD to THC during smoking using some traditional smoking practices was examined before you were in diapers. I realize that's only about 12 to 14 year ago, but it actually dates decades farther back than that

Try cracking a book once in a while.

And no, I won't tell you what, or where.

You're the clinical professional with the pompous attitude, so you must be such an ultrasupergenius that doing it yourself should be a snap.

Have a nice day, kid.











ok.... here's something to think about. In my line of work... when dealing with a person behaving like an arsehole, you should always consider drug or alcohol use.... after all, a drug problem is treatable.... being an arsehole is forever! too bad... so sad ;)

as an aside, if you were as smart as you think you are, you'd know that you're on shaky ground when you jump to conclusions. I would bet that regardless of how far you've gone in your 'education', I'm miles ahead of you.... and that's formal education... not careers without college sort of education but that's up to you to deal with....

[Edited on 14-4-2019 by Nitrous2000]

S.C. Wack - 14-4-2019 at 12:06

Drugs/alcohol may be more effect than cause of personality; maybe you too are only looking so deeply...so...this is what happens when someone without a gold star for social grace feels the need to say how they don't like the response...SWIM you're barking up the wrong tree. The question is unresolved as far as UA-detectable traces go, and really with both CBD sales and employer drug testing it's an experiment that needs doing...I wouldn't expect people selling CBD in smoking formulations to do the research.

Nitrous2000 - 14-4-2019 at 12:38

Quote: Originally posted by S.C. Wack  
Drugs/alcohol may be more effect than cause of personality; maybe you too are only looking so deeply...so...this is what happens when someone without a gold star for social grace feels the need to say how they don't like the response...SWIM you're barking up the wrong tree. The question is unresolved as far as UA-detectable traces go, and really with both CBD sales and employer drug testing it's an experiment that needs doing...I wouldn't expect people selling CBD in smoking formulations to do the research.


There is some truth in the cause/effect question. As far as the ability of social media to convey attitude.... it isn't very good at it.

Around the issues of legally available cannabis products in America and Canada, the onus will be on the vendor to insure that what they are selling is, chemically as advertised. This means 3rd party certificates of analysis with independent proficiency testing.

The really dicey area right now is in fitness to operate a motor vehicle. The laws in this are are totally without scientific backing. A regular user who abstains for a week will have serum/urinary THCCOOH levels above legal limits in virtually all states. AT least in Canada, there will need to be a preliminary failure of a field sobriety test BEFORE having probable grounds for invasive testing. Relationship to intoxication has not been determined (only alcohol). The scientific field is wide open.

Thanks for your comments, S.C.Wack.

Nitrous2000 - 15-4-2019 at 14:50

Quote: Originally posted by S.C. Wack  
It is said 6-MAM can be made with just acetic acid and morphine, i.e. monoacetylation is easy. Unlike morphine IMHO if you want proof you'll have to smoke CBD yourself, preferentially with other subjects. It can be said for certain that 99% of the studies on the effects of CBD do not involve combustion or vapor, and what is known about the safety of smoking CBD is based on hashish, so it's possible that different CBD products produced at different temperatures and atmospheres have bad effects without THC or some other component, and smoking it is not wise.


In fact, diacetyl morphine is easy to make. 6-MAM is made by in vivo hydrolysis of heroin. depending on how the sample is contaminated, there will be mono, di and even tri acetyl codeine. The DEA actually can fingerprint heroin samples where the relative proportions of these analytes define the geographic area of manufacture. But diacetyl morphine is so short lived, we virtually always assay the 6-mam first metabolite.

S.C. Wack - 15-4-2019 at 18:09

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

Not with acetic acid.

Assured Fish - 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.

draculic acid69 - 16-4-2019 at 03:41

No such thing as Tri acetyl morphine

Nitrous2000 - 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.

Nitrous2000 - 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.


Assured Fish - 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.

Nitrous2000 - 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! :)

Nitrous2000 - 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

j_sum1 - 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]

S.C. Wack - 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]

Assured Fish - 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

S.C. Wack - 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]

Assured Fish - 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.

S.C. Wack - 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]

Sidmadra - 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.

draculic acid69 - 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]

formulaswiss - 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.

draculic acid69 - 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.

S.C. Wack - 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]

Nitrous2000 - 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?

S.C. Wack - 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.

Nitrous2000 - 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.

karlos³ - 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).

Nitrous2000 - 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]

karlos³ - 6-5-2019 at 08:50

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