11-OH-D-9-THC More Powerful Than D-9-THC?

Discussion in 'Medicinal Marijuana' started by CheebaMonkey, Dec 25, 2002.

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  1. CheebaMonkey

    CheebaMonkey Sr. Member

    Just a warning that this post is going to be long. Ridiculously long. And a little technical. And completely unorganized. I don't have a clue how to begin this, or how to order it. It's going to talk about 11-OH-D-9-THC, 11-OH-THC, D-9-THC, and Marinol. When I first started to research it, I answered some of my own questions, but I still have a few. I also want to inform people about this.

    To make things easier for me, I have numbered all of the sources I looked at. It's much easier to refer to them during the post.

    1 http://www.nova-institut.de/bioresource-hemp/vortraege/macpartland.htm

    2 http://www.brittain61.org/positions/statemed2.html

    3 http://www.droginfo.com/Enguide.html

    4 http://www.druglibrary.org/schaffer/hemp/history/first12000/14.htm

    5 http://www.nap.edu/books/0309071550/html/36.html

    6 http://www.medmjscience.org/Pages/reports/nihpt2.html

    7 http://www.druglibrary.org/olsen/NORML/WEEKLY/96-09-26.html

    8 http://scienceweek.com/2001/sw010720.htm

    9 http://www2b.abc.net.au/science/k2/stn-old/archive2001/posts/September/427057.shtm

    10 http://smokedot.org/story/2002/9/7/20354/52455

    11 http://babyparenting.about.com/library/blmarij6.htm

    12 http://www.thegooddrugsguide.com/cannabis/effects.htm

    Delta-9-tetrahydrocannabinol is supposed to be the most powerful compound in marijuana. But it does not seem like that anymore after all the reading I have done.

    My interest in 11-OH-D-9-THC began when my friend told me that eating marijuana was more powerful than smoking. Supposedly 3 times more powerful, because your liver metabolizes it into 11-OH-D-9-THC (12).
    So began my search on this metabolite.

    The full name of 11-OH-D-9-THC is 11-hydroxy-delta-9-tetrahydrocannabinol. Try saying that 5 times fast :p.

    When smoked, the effects of marihuana begin to be felt in about five to fifteen minutes. Maximum effect occurs in about sixty minutes. The parts of the body that receive the highest amount of the drug are those which have the richest blood supply, e.g., the liver, lung, kidney, and spleen. Surprisingly, the brain attains relatively low levels compared with these other organs (4). My guess is that when you eat it, more THC reaches the liver and gets metabolized. The same source also said that when marihuana is burned as it is when it is smoked, however, about 50 percent of the delta-9-THC content may be destroyed (4).

    In some of the sources, the metabolite is referred to as 11-OH-THC. Notice the D-9 is no longer there. I do not know if this is important or not. Or whether other delta-#'s also get metabolized into this metabolite. This is one of my questions, to know if it matters or not.

    Because oral doses are processed by the liver before entering the bloodstream, oral THC produces high levels of the metabolite 11-hydroxy-THC, while smoked marijuana does not (7).

    When you digest THC your liver biotransforms THC....when this occurs it produces 11-hydroxy-THC, a compound of equal or greater psychoactive levels than you get when smoking. so, actually your body transforms the THC into a more potent chemical than when smoking. when smoking the compound is 9-hydroxy-THC (10).

    I think that when smoking your liver does metabolize some of the THC, but not nearly as much as eating it. Also the above post states that it turns it into 9-OH-THC, NOT 11-OH-THC. Notice that there is no delta-#, I do not know if that matters.

    After reading through these webpages, they do not agree on the power of 11-OH-THC (I've started to call it 11-OH-THC instead of 11-OH-D-9-THC).

    When comparing it to D-9-THC, some say its equal to 20% more powerful, 2-3 times more powerful, or even 4-5 times more powerful. This is confused even more because some compare it to smoking versus eating, and using the term THC instead of D-9-THC.

    Onto Marinol. A little background info on it, Marinol is actually dronabinol, a synthetic THC. It only contains one THC (dronabinol), and not the other 60+ cannabinoids.

    Additionally, swallowed THC (Marinol) caused more intense psychoactive side effects, due to liver biotransformation of THC to 11-hydroxy-THC (2).

    Responding to the issue of smoked inhalation of marijuana versus orally consumed THC, ElSohly commented that THC in oral preparation "doesn't seem to be doing the good job it should." He speculated that this is because oral and smoked THC produce different pharmacological profiles in the body. Because oral doses are processed by the liver before entering the bloodstream, oral THC produces high levels of the metabolite 11-hydroxy-THC, while smoked marijuana does not. Since 11-hydroxy-THC is four to five times more psychoactive than regular THC, this may explain why some users report a high rate of overdoses and discomfort with Marinol (7).

    Delta-9-tetrahydrocannabinol (THC), the primary psychoactive ingredient in marijuana, is available as a synthetic drug (dronabinol, Marinol). In some studies, however, Cannabis appears to be more efficacious than pure Marinol, and has a lower side effect profile than Marinol. Wherein lies the difference?
    Part of the difference lies in route of administration Marinol is administered orally, and hepatocytes metabolize it to 11-hydroxy-THC, which is about 4 times more psychoactive than unmetabolized THC. In contrast, very little of inhaled THC is converted to 11-hydroxy-THC. The metabolite may explain why psychological "overdose" reactions (dysphoria, anxiety, panic reactions, and paranoia) occur more frequently with oral THC than with inhaled Cannabis (1).

    I also think in addition to the whole 11-OH-THC issue, the lack of Cannabidiol in Marinol allows the user to become higher. Cannabidiol can actually block the high in marijuana.

    Cannabidiol (CBD) possesses sedative properties, and clinical trials show it reduces the anxiety provoked by THC (1).

    If you plug Cannabidiol into a search engine, you can find some studies on it.

    But now this brings up another point. The government and their reefer madness would have you believe that the metabolites that are created from THC negatively affect you because they linger in your body for a few days or even weeks. After reading these pages about 11-OH-THC, and how it is an active metabolite, one would think that is true. But it is not.

    It is gradually metabolized in these tissues to inactive metabolites, the most important is 9-carboxy-THC which is 1/10 as active as THC. Another major metabolite produced is 11-hydroxy-THC, which is approximately 20 percent more potent than THC, and penetrates the blood-brain barrier more rapidly. These metabolites are then excreted in the urine, faeces (2/3) and blood (1/3) (3).

    This sources actually says that THC turns into 9-carboxy-THC, which is supposedly 1/10 as active as THC*. If this is true, I still think that the metabolites are not going to effect the person. 1/10 of something is not nearly as powerful as it originally was. I know that this is extremely anecdotal, but if you search for marijuana and metabolites you will find that they don't have any real negative effects. Except for testing positive on drug tests. The metabolite 11-OH-THC gets metabolized again into an inactive metabolite. But I don't know if an active metabolite is worse than an inactive metabolite. I don't even know what the difference is.

    So you urinate and crap out some of the active metabolites. But thats not the only way your body gets rid of them.

    THC becomes 11 Hydroxy THC. 11 Hydroxy THC becomes Inactive Carboxy THC. Inactive Carboxy THC doesn't affect behaviour. It is, however, detectable in the blood for up to 7 days, and in the urine for up to 11 weeks (9).

    11-OH-THC turns into an inactive Carboxy which does not get your high, but hangs around in your system. I think testing positive for 11 weeks is more towards people who smoke every day, or even a few times a day.

    OK, I think I have covered everything I wanted to. If not, I will just simply post some more stuff.

    To sum up, 11-OH-D-9-THC (or 11-OH-THC?) could be anywhere from being the same strength compared to D-9-THC (or THC?) to 5 times more powerful. It seems to me that the best way to use weed is to ingest it, since it seems the most powerful in that form, and smoking it may actually destroy some of the THC.

    Marinol does not seem to be the wonder drug that it was promised to be. It is costly, and does not work as well as cannabis. If you are interested in reading more about it, I recommend this article, titled "Marinol: The Little Synthetic That Couldn't." Seems to me that natural medical marijuana works far better than any laboratory created synthetic THC. It brings a phrase to my mind, "If it ain't broke, don't fix it."

    I do realize that I did not use all of the sources. This is because they all shared redundant information. I put them there for everyone else to read.

    Finally, I will repeat my questions.

    1. Is there a huge different between 11-OH-D-9-THC and 11-OH-THC?
    2. Why does smoking produce 9-OH-THC while eating creates 11-OH-THC?
    3. What is the difference between an active and inactive metabolite?
    4. Is an active metabolite more dangerous (or have more of a good or bad effect on your body) compared to an inactive metabolite?

    That's all I have at the moment.

    Any additional information about this topic would be greatly appreciated.

    * As I sit here and read over my post, I end up reading over the 1/10 as active part. I am beginning to think that 9-carboxy-THC does not get you high. It seems that it is considered inactive because it is 1/10 as active as 11-OH-THC. But this does not mean that it will get you high. The article does not say that it will get you high, but then again it does not say that it will not. Perhaps a metabolite is considered inactive because its effect on the body is so little that while it may technically be active, it is considered inactive. Hopefully someone will know more about this.

    I feel that I will end up posting some information about metabolites and their effect on your body related to cannabis.
  2. FreudPhilly

    FreudPhilly New Member

    Did your other thread get locked or something? I already replied to that one.
  3. ikari

    ikari Seasoned Activist

    That is a very interesting post, and what you seem to be saying is plausible.

    I have no answers to the questions you proposed, mostly because I havn't researched this enough.

    However, I hope you would consider this:
    Although when ingesting, the high lasts much longer, you will never get as high as a peak as when smoking.

    It's as simple as that.

    The reason is because the lungs absorbtion rate is so much faster than that of the intestines, it's physically impossible for the stomach/intestine to process the marijuana fast enough to provide the "super-baked" peak that smoking can create.

    I post this so that people dont run out and eat a 1/4 of weed expecting to get as blitzed as when taking huge gravity bong hits. Sure, you WILL get stoned, and it'll last for a REAL long time, but it won't peak as high.

    I was always under the impression that because the GI tract is so slow, that it takes a long time to process marijuana and thus this prolongs the high.

    However, perhaps your explanation of the 11-OH-D9-THC explains why the high lasts so much longer.. however, it's kind of debatable, because if it was truely that much more potent, you'd think it possible (even with the slow GI tract) to hit a peak higher than smoking.. which it isn't.. (im suggesting the extra potency would compensate for the slow digestion system)
  4. ChronicMasta

    ChronicMasta New Member

    maybe.. but i still find altough no peak a plateau which last much longer when eating/.. sure u may not reach the peak but the plateau is close enough and last longer which makes up for it.. also the act of smoking the herb itself is more fun than eating waiting for an hour then getting gradually higher and staying high though out the day.. i've tried smoking and eating.. eating is better when u want to be baked for a long time.. smoking is better for a nice high .. in the end its all about preferences..

    interesting thread Cheeba..
  5. CheebaMonkey

    CheebaMonkey Sr. Member

    That's a good point ikari.

    But I think that if you do eat enough weed, and it is potent enough, you should be able to get just as high, maybe even higher. I was reading a post where someone made cookies and was so stoned they couldn't move. For five hours. That's pretty stoned.

    Yeah, in the end it all depends on the user.

    I haven't found any answers to my questions, but then again I haven't really been looking. I should do that.

    Another interesting thought. Why not combine both eating and smoking? Gravity bong hits and bud brownies. I wonder what that would be like?
  6. ikari

    ikari Seasoned Activist

    Combining would be a crazy ride, that's for sure!

    The most stoned I ever was when was when I smoked a huge joint really fast.. it was about an 1/8 of weed, and I started honost to God hallucinating.

    I don't think even if I ate an ounce or more of weed I would ever get that.
  7. bongwater

    bongwater New Member

    waht if you smoked weed, which would get your peak up really, AND ate some, so that you peaked, then fell to a lower high for a longer time.

    well lets just say if you ate weed your "highness" would be a constant five (out of 10) and if you smoked, it would go up from 1-10 adn then back down but wouldnt alst as long..now if you smoked and ate, it would go up to 10, then come back down to a five and last as long it would last just by eating.

    if that doesnt make sense, ill compare it using batteries. Eating weed is like hooking 2 batteries in parrallel. they last twice as long as 1 battery. Smoking weed is like hooking 2 batteries in series, you get twie the volatge, but last as long as one battery. so smoking adn eating is like hookinh two batteries ins eries, with 2 batteries in parralell, so they last twice as long with twice as much power for a certain amount of time. hope that makes sense
  8. PattyD

    PattyD New Member

    an active metabolite i believe means that it will metabolise and thus leave your body a lot quicker probably bc of its chemical make up whereas an inactive metabolite probably requires some kind of chemical reaction in the body to initiate its breakdown but either way if you have high metabolism it doesnt matter and about that really dank thc weed i wouldnt want to waste the thc by burning it so if i was going to smoke it id smoke with one other person and after one person took a few hits in a row blow the second hand into the others mouth and vice verca but if i ever got that kind of dank **** id probably just eat it so i wouldnt **** it up lol the best i can get around here is mid grade but its better than nothing
  9. beats

    beats New Member

    And yet they say stoners are stupid, sheesh, I bet the average joe wouldn't have a clue what Cheeba just said.

    That little report was very informative and it makes you think alot. I'm still not sure if 11-OH-THC is more powerful than D-9-THC (I'm going to figure it out while typing), because the effects are very different between ingesting and smoking (this is considering that smoking does not convert the D-9 to 11-OH) maybe it is just the way it is absorbed into the blood stream. When smoking the weed it is absorbed much faster and therefore travels to the brain faster, causing more 11-OH to "hit" the brain at one time, whereas ingesting causes it to slowly "blanketing" the brain with the 11-OH, maybe part of the high from smoking it is caused by a slight brain overload?

    I doubt that but I'm thinking this all through. Also smoking causes the THC (11-OH or D-9, take your pick) to get to the heart faster, so it goes straight to the brain to give you your high, but eating it makes it go into the stomach, where it is digested, spread throughout the body, causing our "body high" that we get form eating.

    As to question #2, maybe the process used in distributing the THC through our body change the chemical structure of the the said THC, maybe some of the stomach acids, or when it is absorbed through the intestines it is changed into 11-OH, and when it is absorbed through the lungs, it stays relativly the same(It's originially D-9 correct?), because the lack of acids, or different absorbtion process. Either way I believe post is very thought-provoking, and I plan on posting more thoughts (probaly some ones with actual truth, as opposed to my ramblings) after i re-read and re-read this.
  10. beats

    beats New Member

    I was listening to the dead and it came to me!

    I think that 11-OH-THC is a sort of toxin. That is why it is possible to "overdose" while eating marijuana. It must be the toxic form of THC, because D-9-THC cannot easily be overdosed on. I think the reason we can "overdose" on 11-OH-THC is because it is a toxin, or has toxic traits. Hmmm

    I hope this is right, it seemed like a revelation to me.
  11. ikari

    ikari Seasoned Activist

    Sorry, where did this overdosing thing come from? I have never heard of it.

    I mean, you can overdose on THC.. it just takes such an incredible amount that it's physically impossible. And as far as I know, this applies to eating it as well.
  12. beats

    beats New Member

    It's not really overdosing, but too much in your food will make you nausous and you can throw up. I did it once, and so have my friends.
  13. CheebaMonkey

    CheebaMonkey Sr. Member

    Boy it's been awhile since I've posted in this thread.

    I'm not trying to pick apart your posts beats, but it's just easier to explain it if I do it that way.
    I think 11-OH-D-9-THC is more powerful than D-9-THC. But that's just me. :)

    The "high" isn't different because of the way the molecules "hit" your brain, it's the different types of them, and the quantity of them.

    When you smoke, you inhale the THC into your lungs, which gets absorbed into your bloodstream, which from there travels to all sorts of places in your body.

    One of the pit-stops along the way that blood travels is your liver.

    The liver will biotransform the THC; one of the metabolites is 11-hydroxy-THC. Some 11-OH-THC is produced when you smoke, but its concentration seldom reaches psychocative levels(27).

    When you smoke, the culprit for getting you high (that has the biggest role in it, others take part, such as D-8-THC, is D-9-THC. To go off even more in this tagent, only D-8-THC and D-9-THC show all psychoactive effects of marijuana. But D-8-THC is slightly less powerful than D-9-THC, and D-9-THC is more abundant than D-8-THC, thus D-9-THC gets much more credit for the effects of marijuana. D-8-THC is found only in few varieties of the plant (Hively et al., 1966)) is D-9-THC. It gets absorbed into your blood, travels to your brain, binds with cannabinoid receptor sites, and kablamo, you get high as a result.

    I'll go more into depth of 11-OH-THC and your digestive system later on.
    I'm not too sure if the molecules getting spread throughout your body are responsible for the "body high." There are CB1 (and possibly a subtype called CB1A) receptors found in your brain and central nervous system (CNS), and CB2 receptors found in the cells (and other places) of your immune system. I don't know if the binding of 11-OH-THC (or D-9-THC) to CB2 receptors found in your immune system produces psychoactive results. I think psychoactivity is limited only to receptors found in the brain, but then again, I could be wrong, I'm not too sure. Anyone with information on this subject would be helpful.

    I'll just leave it at that until I have more info.

    When I was finishing up this post, I found this.

    Despite these similarities, cannabinol is probably more active in the immune system than in the nervous system. In contrast, THC is probably more active in the nervous system than the immune system (IOM, 1999).
    Yes, THC can get changed into something else when it's in your body. The liver will do that.

    When D-9-THC is absorbed into your bloodstream because of your lungs, very little of it will reach the liver, and even less of that will actually get biotransformed into 11-OH-THC. So the plant cannabinoid that binds with the receptors in your brain when you smoke pot is mainly D-9-THC.

    Okay, here's the part about 11-OH-THC and your digestive system I promised.

    Let me briefly and simply describe the digestive sytem, because I don't know that much about it. :p

    You eat something, in this case bud brownies. Mmmmmmm. You chew it up, it goes down your throat, into you stomach. Your stomach is breaking down the food so that it can be transported to your small intestines. A side note, other organs help out the small intestines, such as the liver, gallbladder, and pancreas. The nutrients (and other stuff, maybe not so nutritional) are absorbed in the small intestines, and get sent to the liver and other body parts to to processed, stored, and distributed.

    Now here's the snag. It's 3 in the morning and I want to go to bed. Well, not really.

    Errr, I mean, the THC gets sent to the liver where it undergoes biotransformation. Yeah, that's what I meant to say.

    For example, when Marinol is swallowed, it must move from the stomach to the small intestine before being absorbed into the bloodstream. This takes time. After absorption, orally consumed THC passes immediately through the liver, where a significant proportion is biotransformed into other chemicals. Due to metabolism by the liver, 90 percent or more of swallowed THC never reaches sites of activity in the body(20). Infact, two hours after swallowing 10 to 15 milligrams of Marinol, 84 percent of subjects had no measurable THC in their blood. After six hours, 57 percent still had none(21).

    That's not good for some medical marijuana patients.

    One way to use cannabis without smoking or eating it, and keeping the THC from getting transformed into 11-OH-THC is by using a suppository. Suppositories deliver the drug directly into circulation, while avoiding the liver.

    I'll tip my non-existant hat to anyone who inserts marijuana rectally to see if they get high in the name of science. :indiffere
    If you are going to say that 11-OH-THC is toxic, you have to say that D-9-THC is toxic as well. There is a thread here about THC and toxicity.

    Here's some interesting information about LD50's (lethal dose) and method of administration, in this case orally.

    Scientists have manage to give up to 9000 mg/kg doses of THC orally to monkey's without killing them. What does this mean if we try to relate it to humans?

    For example, take a 70 kg (154 lbs.) person. If we try and relate the monkey doses to the human, they would have to consume 630,000 mg (or 630 grams), or expressed in pounds, about 1.39 lbs of pure THC to equal the amount the monkey's were given. An average human stomach can hold about 2 lbs (chances are it has to be liquid only, good luck trying to fit 2 lbs. of solid matter in there, unless of course you competitively eat. I remember some Asian guy ate 50 hot dogs and hotdog buns). So I suppose, in theory a person can overdose on THC (if the lethal does orally required you to eat less than 2 pounds, hasn't actually been proven, this is just a thought of mine) if they eat a greater amount than 1.39 lbs of pure THC.

    But keep in mind were trying to relate the information we gathered from the monkey experiments and apply it exactly to humans. That doesn't work correctly in reality. We're not all monkey's (except for me of course :p).

    There has yet to be a lethal dose established in humans.
    That sucks.

    Something interesting I found.

    An intoxication desired by cannabis consumers requires inhalation of at least 10-15 mg THC. Chronic consumers need higher doses because of their development of tolerance to the active agent. This was shown in a study where 47 chronic Cannabis users tolerated inhaled THC doses of up to 180 mg without undesired side effects or nausea (Stefanis 1978).

    Normally, you only need around 10-15 mg of THC to get high, but some people managed to take a 180 mg dose without any negative side effects.

    Okay, I'm done. For now. :)

    Later on I'll post some more stuff about what I originally wrote.

    27. Mason and McBay (1985), Agurell et al. (1986), Lemberger et al. (1973) Perez-Reyes et al. (1973).

    20. Mattes, R.D. et al., "Cannabinoids and Appetite Stimulation," Pharmacology Biochemistry and Behavior 49: 187-95 (1994); Peat, M.A., "Distribution of Delta-9-Tetrahydrocannabinol and Its Metabolites." Advances in Analytical Toxicology 2: 186-217 (1989); Wall, M.E. et al., "Metabolism, Disposition, and Kinetics of Delta-9-Tetrahydrocannabinol in Men and Women," Clinical Pharmacology and Therapeutics 34: 352-63 (1983); Agurell et al. (1986).

    21. Mattes, R. D. et al., "Bypassing the First-Pass Effect for the Therapeutic Use of Cannabinoids," Pharmacology Biochemistry and Behavior 44: 745-47 (1993).
  14. beats

    beats New Member

    But see, I was just saying all that without having a clue about what it was :p heheh. I was just rambling on, didn't think I was right, just felt like writing.

    Are you really smart or something? (heheh what a great question)

    And I hadn't smoked for a long time up to that nauseous "episode". I was celebrating with some cookies, I overdid it.
  15. opteek

    opteek New Member

    It's physically impossible to overdose while smoking, but it is possible to overdose with ANY substance.
  16. beats

    beats New Member

    Sorry bud, but that makes no sense
  17. CheebaMonkey

    CheebaMonkey Sr. Member

    Oops, I hope you don't think I was attacking you beats, I was just trying to explain it to you :)

    How many cookies did you eat?

    Okay, I sent an E-mail to cannabis-med, and they told me that activiation of CB1 receptors causes psychoactive effects, activation of CB2 does not.

    My link about 9-OH-THC apparently doesn't work anymore, I guess abc.net didn't like what they were talking about. I don't think smoking creates 9-OH-THC and not 11-OH-THC. So forget about that question.
  18. beats

    beats New Member

    Oh don't worry, I don't get offended, life's too short.

    And to that question, it wasn't so much the quantity of cookies, but that quantity of the "Special ingredient" :p That may have been the problem in itself.
  19. opteek

    opteek New Member

    It is physically impossible to overdose on 'THC' if you are smoking it. Reason being that you will pass out before the levels near overdosing. If you are smoking hash, you will begin vomiting before the levels near overdosing.

    However, it is possible to overdose on any substance.

    One could, in theory, intravenously consume large amounts of concentrated 'THC' which would certainly reach a level of critical overdose.
  20. beats

    beats New Member

    I thought you meant that, just remember to word things better ;)
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