From: bprofane@netcom.com (Gert Niewahr)

Isomerization

Isomerization: This method is out of "Dr. Atomic's Marijuana Multiplier," one of those early 70's doper pamphlets. This process assumes you have pure hash oil to begin with.
"Dissolve the hash oil in absolute ethanol or pure methanol in the ratio of one gram extract to ten grams solvent. There must be no water in this solution, as the next step is the addition of one drop of 100% sulfuric acid per gram of extract. Add the acid slowly, drop by drop, stirring slowly and completely, with a long glass stirring rod. Place a Pyrex pot containing the extract-alcohol-acid solution into the refluxing apparatus and reflux for two hours. The acid will not evaporate and will remain in the Pyrex pot. Allow to cool. Take the cooled solution, pour with an equal volume of water and 1/2 volume of petroleum ether into the ether-extraction apparatus (separation funnel). Allow to settle, and drain the ether extract layer. This leaves an ether-extract-acid mix from which the acid must be purged. To accomplish this, pour the ether-extract-solution into four volumes of 5% sodium bicarbonate solution (1 gram bicarb. in 20 grams of water). This will neutralize the acid, releasing CO2 and leaving a solution of sodium sulphate. Allow this to settle into layers, then drain the ether-extract layer. Mix the ether-extract solution with an equal volume of pure water and let it separate. Drain off the ether-extract layer. Evaporate the ether and what remains is hash oil in which all of the cannabinoids have been converted into THC."

Oh my, having just typed all this in, I thought to check my copy of "Cannabis Alchemy" for a method. Not only does it concur with this method of isomerization, it has lots of whiz hints on fractionally distilling hash oil to get an ultra-pure product. It also claims that if you convert THC to its acetate, it becomes very potent and psychedelic. Yow.
A shorter description of the procedure is available in "Marijuana Chemistry" by Michael Starks. ISBN 0-914171-39-9
Posted anonymously:

Apologies if this question has been answered before, but my newsreader tends to miss a lot of postings.

Treatment with acid, according to my understanding, does not cause isomerization of THC, but converts the cannabidiol to delta-9-THC. Since cannabidiol represents a significant proportion of the cannabinoids in extracted plant material, making this conversion can make a big difference in the potency of the product.

In the dim, dark, distant past I have treated extracted plant materials with 0.05% HCl in ethanol by refluxing for 2 hours. I have never done a controlled study to determine if this was doing any good, but I can verify that it certainly doesn't do any harm.

Pertinient references (for completists):


From: andy@eng.tridom.com (Andrew P. Klenzak)
Subject: Isomerization
Date: Fri, 17 Dec 1993 20:18:54 GMT
In article A8644wk@asb.com,  max.fordham@asb.com writes:
>NE>>Have you folx heard any of "isomerization" of hash oil?  Supposedly,
>NE>>treating hash-oil with dilute HCl acid under certain circumstances
>NE>>allows conversion of some weak/non-psychoactive THC's in the oil to the
>NE>>more potent delta-9 THC.  In some cases, it is reported to increase
>NE>>potency by 3-5 times, depending I guess on the ratios of weak THCs in
>NE>>the original material.  Something about "isomeric rotations of
>NE>>the THC molecules" or something.... Anybody interested, I'll give ya
>NE>>some references as to where to find info on thee process next time...
>
>NE>Yes very interested!!  Tell me more!  Tell me more!
>
>OK, now that I have my copy of "Dr. Atomic's Marijuana Multiplier" in
>front of me, I see that he used Sulfuric acid, not HCl.  Isomerization
>coverts cannabidiol and weak THCs to yer favorite #9.  Anywhere from
>double to 5 times original potency. 

   per Cannabis Alchemy,
  
Cannabidiol
     |
     | Heat and
     | H+ (from the acid)
     |
    \ /
  
Delta-9 THC (using formal numbering)
Delta-1 THC (using monoterpenoid numbering)
     |
     | Heat and
     | H+ (from a stronger acid acting longer)
     |
    \ /

Delta-6 THC (aka Delta-8 THC -- depends on the numbering system used)
  

This Delta-6 THC is a higher-rotating form of tetrahydrocannabinol. D. Gold (author of Cannabis Alchemy) suggests that the higher-rotating forms "are more potent than the low-rotating and produce a higher, more psychedelic and spritual effect." He notes a study done by Mechoulan (1970) which showed little difference between the pharmacological effects of Delta-9 and Delta-6. I'll leave it to the reader to experiment for him/herself.

The "rotating" spoken of here refers to the relative positions of the double bonding in the THC molecule. [chemists out there feel free to chime in...]

The first reaction, Cannabidiol --> Delta-9 THC, is, I think, what is generally referred to as isomerization. This can occur in an absolute ethanol solution with .05% HCL boiled for 2 hours (the "hash" oil is in solution in the ethanol, obviously). The increase in potency you'll get depends on the relative amounts of Cannabidiol and THC in the original oil. If there were 1 part THC and 1 part Cannabidiol, then you might expect a doubling of potency after isomerization.

The second reaction, Delta-1/9 --> Delta-6/8, is an additional step to get the allegedly more potent higher-rotating form of THC. It requires more vigorous conditions. D. Gold notes that in a toluene solution with p-toluenesulfonic acid for 10 hours at 100 degrees C there is a 90% conversion rate of Delta-1 to Delta-6 (the THC/hash oil is in solution in the toluene).

Gold also gives a discussion about producing THC acetate, which he says has twice the potency of regular THC. It's very involved, and potentially hazardous...

>Instead, I would recommend either/or/both _Cannabis_Alchemy_(CA) by
>Gold, approx.US$12.95(prices from an old catalog from '92), or better
>yet, _Marijuana_Chemistry_(MC), by Starks, for about US$19.95.
>
>I've "paged through" CA, and it was reasonably detailed, etc, though,
>from what I have heard, the higher price of MC is well justified by the
>great thoroughness.
  

I haven't seen Marijuana Chemistry, but CA is not real heavy into the theory and chemical conversion steps, but does include a few pertinent references/citations and lots of practical how-to advice and instructions.

It's the holidays folks -- go ahead and order them both and do some fun reading. You'll most assuredly learn something.


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