Author Topic: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth  (Read 5394 times)

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lugh

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #20 on: July 25, 2001, 04:10:00 AM »
Actually, Cannabis Alchemy uses the acetic anhydride method, and gives no reference to the originator. The author is certainly no highly trained chemist, since he insists one build a nitrogen filled glove box to handle acetic anhydride. It's a good box for doing more dangerous work, just overkill with the very obnoxious acetic anhydride. So if you actually obtained THC acetate by this "mistake in memory" you'll have repeated the same process that has led to many other great discoveries in chemistry that were made by a similar mistake. Nobody should be laughing, this may very well be a great advance in THC chemistry. We'll know when someone is able to duplicate your results. Advances in science are sometimes improbable.

superhybrid

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #21 on: July 25, 2001, 05:25:00 AM »
It has been three years since Cannabis Alchemy was read and it was thought for sure they used glacial acetic acid. A fischer reaction has been done before using the acetic acid route and if memory serves me right the yields were above 80%. H2SO4 was used and if it was wondered that was the reason for using it again. Must go with what one knows as also available. Acetic anhydride is a little harder to come by than glacial acetic acid.  

With equimolar amounts of acetyl chloride and NaOAc one can form acetic anhydride which I am sure was already known. One only needs thionyl chloride and acetic acid to form acetyl chloride if memory is correct.

lugh

  • Guest
Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #22 on: July 28, 2001, 03:51:00 AM »
Those that think Cannabis Alchemy's acetylation procedure using acetic anhydride is the only course should read Journal of the Chemical Society 75, 20 (1899), in it cannabinol is acetylated by refluxing with either acetic anhydride or acetyl chloride. While this isn't definitive support for Fischer esterification of cannaboids, it does show that the author of Cannabis Alchemy didn't fully research the matter. In the same vein, in support of Dope Amine's post, Raphael Mechoulam's structure activity table shows that THC has the same physiological effect as THC acetate with only half the dose. What we can learn from this is something that many of us already knew, that books of this type are very often filled with misinformation.

Rhodium

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #23 on: July 28, 2001, 06:51:00 PM »
Could you direct me to that SAR by Raphael Mechoulam? I cannot find it with a websearch.

https://www.rhodium.ws


terbium

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #24 on: July 28, 2001, 10:23:00 PM »
I find it in a table in the book Marijuana - Chemistry, Pharmacology, Metabolism and Clinical Effects, Edited by Raphael Mechoulam, Academic Press, Publ. 1973, Library of Congress Catalog #72-77349

Chapter 2 - Structure Activity Relationships, Table V - Activity of delta-1 and delta-6-THC Derivatives and Related Materials. This table gives the dosage necessary to produce certain observable effects in rhesus monkeys: - indicates no change; +-, tranquility; +, drowsiness,decreased motor activity,occasional partial ptosis,occasional head drop; ++, stupor, ataxia, full ptosis, suppresion of motor activity, typical crouched position ("thinker position") for up to three hours, presence of reaction to external sensorial stimuli; +++, severe stupor and ataxia, full ptosis, immobility, "thinker position" lasting for more than 3 hours and absence of reaction to external stimuli.

From the table:

Compound        Dose (mg/kg)     Activity

(-)-delta1-THC            0.05                     +
                                0.1                      ++
                                0.25                     ++
                                0.5                      +++

delta1-THC acetate        0.2                      +-
                                  0.5                      +
                                  1.0                      ++

(-)-delta6-THC            0.1                      +-
                                0.25                     +
                                0.5-0.9                  ++
                                1.0-2.0                  +++

delta6-THC acetate        0.2                      -
                                  0.5                      +
                                  1.0                      ++
                                  5.0                      +++

superhybrid

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #25 on: July 29, 2001, 04:11:00 PM »
The above table makes it seem that the acetate was possibly not worth acquiring. It was thought that potency doubled by adjoining the acetyl group.

goiterjoe

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #26 on: July 29, 2001, 05:50:00 PM »
I seriously doubt the guy did enough experimentations with different monkeys and different dosing times for any of his statistics to be valid.  Monkeys build up tolerances just like us, and not all monkeys have the same mental capacities and reactions to diferent chemicals.  and who's to say that his chart shows the acetates are less active?  he tests to see how much it takes to make the monkeys immobile, but maybe the acetates produce a speedy high?  My experiences with THC acetate have been that it takes a long time to kick in, it lasts a lot longer than regular THC, and I'm productive when I'm on it.  Mexican dirt weed puts me in the fetal position, but that damn sure doesn't mean it's the bomb shit. 

If pacman influenced us, we'd glide around dark rooms eating pills and listen to repetitive music.

Osmium

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #27 on: July 29, 2001, 06:24:00 PM »
As far as I know Mechoulam is THE pimp daddy of THC chemistry, I even seem to remember he was the one determining the structure. I wouldn't be so fast in arguing his findings.
Mokeys aren't cheap, they aren't wasted for experimentation like rats. It's very well possible that he used the same group of monkeys for lots of his research, so these lucky creatures really could have been VERY used to THC and the like.

b159510

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #28 on: July 29, 2001, 06:48:00 PM »
As far as I know Mechoulam is THE pimp daddy of THC chemistry, I even seem to remember he was the one determining the structure..Interesting info. Two other chemists were (also?) key in determining the structure of THC; Sir Alexander Todd ( Nobel Prize for work on nucleotides) and Roger Adams Ph.D., clarified the structure of THC, and showed that the test used by the FBI to detect THC actually was detecting an inactive companion chemical found in marijuana. Gotta luv those old-school guys. :)

Back to the Primitive

lugh

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #29 on: July 29, 2001, 10:19:00 PM »
All three of these gentlemen played instrumental roles in the clarification of cannaboid chemistry, Adams was the first to isolate pure d6-THC, Mechoulam and Shvo determined the stereochemistry in 1963. Many others played important roles as well. THC acetate may very well affect different people in a different manner, individual body chemistry's differ. What's important about this discussion is that we probably have a simple new method for producing the acetate, for those that enjoy it, and the best methods for extraction have been discussed. The pharmaceutical percolator is the preferred tool, it is designed expressly for this purpose. High vacuum distillation will produce 90% THC oil very easily.

superhybrid

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #30 on: July 29, 2001, 11:42:00 PM »
It is possible that somehow the acetate has to be deacetylated before it is active; same or similar to diacetyl morphine. Chemgrrl gave a reference to the deacetylation of morphine in the brain and it was learned in class to counter the affects of cocaine they are forming compounds/enzymes to de-esterize the cocaine molecule since it is a diester. We all have these enzymes but some more than others as possibly hyperactive people do. Cocaine never did much for some subjects known personally and here at the hive.

 The explanation given for the above water solublity is that the alkaloids present formed amides which may or may not increase solubility. If one wanted to break these amides I believe the extract could be refluxed gently with HCl.

Lilienthal

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #31 on: July 30, 2001, 03:26:00 AM »
I seriously doubt that amides ar formed from amines under that conditions. And even if so they wouldn't be much more hydrophilic.

superhybrid

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #32 on: August 03, 2001, 05:47:00 AM »
Lil, amides are formed by this process under reflux. It is a simple dehydration reaction in which H2O leaves the reaction but at the same time it is also reversible. I am sure there is a equilibrium point and most likely the product only went to 30 to 70% completion for the formation of the amides but as is known amides are quite water soluble so indeed if there was only a small amount of amide it may be enough to dissolve alot of the acetate and THC non ester since this reaction/'s is reversible.

Anything else?

Lilienthal

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #33 on: August 03, 2001, 08:17:00 AM »
::)

goiterjoe

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Re: Cannibinol -->d-6-THC -->d-6-THC Acetatete synth
« Reply #34 on: August 03, 2001, 04:48:00 PM »
I'm not doubting his ability as a chemist by any means, but he might not have used the best techniques to study chemical activity.  I guess you can't expect every researher to be like Shulgin though.  Hell, I downright loathe the THC high, so I would probably experiment with rats and monkeys as well.

Drunk driving, that's what I like to do,
I like drunk driving with you.