CardinalLaw (Stranger)
01-07-03 10:26
No 396178
      Context of the delta in delta-9-THC?     

Found a THC extraction in chem library. It involves using hexane as the solvent. Can hexane be obtained from a hardware store?  And what does the delta mean? I've only known it to mean "change in" something. And what are the differences between delta-7-THC, delta-8-THC, or delta-9-THC. Most importantly, whats the good stuff that can be smoked?

What's right one day is wrong another.
(Chief Bee)
01-07-03 13:51
No 396228
      The different deltas
(Rated as: good read)

Under the term tetrahydrocannabinol (THC) there are three known physiologically active isomers, which differ only in the bonding in the left-hand ring of the molecule:

The preferred numbering for the isomers is based on the mono-terpene numbering scheme[1] (used here) although other systems are used and confuse the literature[2]. The isomers have been designated here as follows;

THC-A's can be easily isomerized-to THC-B's by heating with p-toluene sulphonic acid in nearly quantitative yield[3]. The syntheses of THC-A, THC-B, or THC-C are all based on the condensation of olivetol (5-(n-amyl)-resorcinol) with a second component which forms the left-hand and center ring of the THC molecule. THC-A or THC-B are obtained from olivetol and one of the following; citral, (-)-verbenol, or (+)-p-2,8-menthadien-2-ol. THC-C is obtained from olivetol and (-)-2-carbethoxy-5-methylcyclohexane.

[3] JACS 90, 2420 (1968)
(Hive Bee)
01-07-03 13:57
No 396234

Use acetone in extraction it will do the job, mik oil that has left after solvent evaporation with mj. powdered leafs and you will have hash.
Ideal for converting lousy mj. to good hash.
01-07-03 15:57
No 396264
      Acetone will rip the crap out of the weed.     

Acetone will rip the crap out of the weed.  No, no ... too many impurities will be extracted with acetone.  Reflux the weed in petroleum ether (or let it soak in it for a day). Strain, saving the petroleum ether/oil mixture... pressing out the material thoroughly to get as much solvent/oil out of the material as possible. cool
See page 6 of this document - although it doesn't say much ...

Just One Fix
(Master Searcher)
01-07-03 16:03
No 396270

UTFSE for Bestine.
The hardest thing to explain is the obvious
01-07-03 16:25
No 396276
      Huh, who is Bestine ? 8-O     

Huh, who is Bestine ? shocked

Just One Fix
12-21-03 01:25
No 478145
      THC chemistry     


I'm reviving this post because I want to talk THC chemistry, and Rhodium has conveniently posted a chemical structure above. I realise THC is not exactly number on fav around here, but I have this hypothetical situation which involves a couple of pounds of homegrown MJ having been buried underground for about 5 years now, due to disinclination to do anything with it. The time has now arrived.

<rant> I am fully aware of how to make hash oil, and what I do not want is 10 f*ck*ng stoners chiming in with 10 of their f*ck*ng different recipes, as the FSE suggests seems to happen every time this topic comes up. What is being sought here is chemical understanding, OK? Otherwise, there will be consequences - you have been warned! <\rant>

Ideally, I would have liked to post graphical structures as well for THCA, CBD and CBN, but I strongly suspect those of you who can help me don't need them. To recap, THC is the trippy substance that is generally most desired (structure above). CBD is more sedating and differs from THC in possessing a phenol instead of the cyclic ether. CBN is said to be a less psychoactive, oxygenation product of THC, and differs in possessing more double bonds in the far left ring. The Merck also says that it is soluble in OH-, unlike THC and CBD (I don't quite understand why all of them don't form water-soluble phenolates, a la morphine). Most of these substances actually exist in the wild with an additional carboxylic group, and are said to require heat to become decarboxylated and therefore psychoactive. Onto some questions:

1. Decarboxylation. Most people don't seem to bother with it, presumably because they are anticipating smoking or cooking with the product ultimately. However, I have seen some research which suggests that the acids have different solubility properties and could be unintentionally discarded during either extraction or washing: So some pre-processing would seem desirable, and the obvious thing to do is cook the weed in a low temp oven. Fair enough, but prolonged exposure to alcohol at room temp would also seem to do the trick, otherwise steeping MJ in booze would not work, which it does. The suspicion arises that any protic solvent might do it, and in fact a simple water boil could be enough. More elaborately, an acidic isomerisation reflux could also do it. Any comments?

2. Isomerisation. As suggested above, this is really conversion of a phenol to a cyclic ether, and the conventional method involves a reflux with mineral acid. Previous posts are a little hazy on the subject of whether this reflux must be anhydrous or not. Water would not seem to be a product, so maybe it is not necessary to go overboard with water scavenging techniques here?

Another question is does the solvent matter? I have seen one post suggesting alcoholic solvents are bad news due to byproducts. On the other hand, enquiring minds want to know whether a little polarity would maybe be a good thing for acid distribution? Similarly, is there anything in the weed extract which potentially could fuck this up? I believe chlorophyll consumes more acid, but that is no great disaster.

Photochemistry comes in here. The conventional wisdom is that light degrades both THC and CBD, but one source I respect claims actually to have used light to promote isomerisation. Comments anyone?

3. Increasing potency. No-one seems to be able to decide whether the acetate ester is more or less potent, and I don't really expect that to get resolved now. Ditto the issue of whether GAA is enough, or whether acetic anhydride is required. However, I am intrigued by the idea that a toluene/H2SO4 isomerisation forms the more potent delta 6 THC. The obvious question which arises here is whether this is possibly due to the formation of a sulphate ester? (which would be mega-convenient). And one again, do we need a water scavenging technique here?

On the downside, there is a whisper around that these esters, whether or not they are stronger, may not be particularly stable. Anyone? The other obvious manipulation which I have rarely seen discussed is halogenation, either of the hydroxyl or (more likely) of the ring. Anyone got any ideas whether this is worth pursuing?

4. Reduction of CBN to THC. The word seems to be that THC degrades whether or not it is exposed to atmospheric oxygen, yet no-one seems to be concerned about reversing the process. Further, the temperatures and O2 exposure involved in isomerisation could very well hasten the process. In principle, reversal could be quite a facile reduction/hydrogenation, eg, nickel formate in a pipe bomb, or even a Zn cathode, acidic catholyte, and STP conditions. Anyone?

Whilst I am going on, I don't fully understand the mechanism of this so-called oxidation. One question is whether the hydroxyl is involved? For that matter, if I leave cyclohexane in a beaker on the bench, I don't expect to come back later and find benzene. Anyone with any clues here? Lastly, would there be any value in adding an anti-oxidant to one's oil? Questions arise here about how well sodium ascorbate/metabisulphite might work in anhydrous and apolar conditions ...

5. Extraction. Not so hard you say? Well no, but someone who shall remain nameless once decided to boil off his pet ether from the oil in an open saucepan. The resulting product refused to dissolve in anything but vegetable oil, suggesting polymer city. Correct? More generally, it would seem that solvent stripping should ideally occur with minimal heat, and maybe under an inert atmosphere. Anyone got any ideas how critical both oxidation and polymerisation are?

All sensible discussion appreciated ...
(Chief Bee)
12-21-03 08:06
No 478188
      THC Acetate & isomerization     

I feel that the issue of "THC Acetate" is already resolved, see Post 342953 (Rhodium: "R. Mechoulam rates higher than D. Gold", Novel Discourse) - I would also expect the ester to be more stable than the phenol itself, as long as all traces of acid is removed from the product. I find it unlikely that you could acetylate a phenol with plain acetic acid - acetic anhydride is needed.

Regarding the isomerization - you probably don't need strictly anhydrous conditions, as long as you don't make it a two-phase reaction - the acid and the THC must both be dissolved in the same (non-polar) phase for the reaction to take place.

The Hive - Clandestine Chemists Without Borders
12-22-03 01:48
No 478378
      Oh, and another thought after the event: might     

Oh, and another thought after the event: might there be any value in an alkaline wash of the initial extract, in order to remove fatty acids? Obviously, that would also remove CBN, but seeing that no-one seems to be concerned with doing anything with it, that could actually be an advantage.
12-25-03 11:16
No 479019

Preliminary trials to react olivetol with terpenes in 0.1 molar HClO4 in acetic acid (the stuff that is used for non-aqueous titrations of weak bases) showed that there was indeed lots of reaction going on in just no time at all - but the molar mass (GC/MS) of most products suggested that also esterification had occurred.
I wouldn´t be so sure that an acetate ester of delta-9-THC is that much more stable to oxidation as it is the terpene-part of the molecule that has its hydrogen stripped off when THC becomes CBN (which is the main product on oxidative breakdown from exposure to oxygen). Actually  CBD, which sports two phenolic hydroxy-groups, is pretty much stable - so this suggests an even greater sensitivity of THC-esters towards aromatization of the terpenoid ring than that of THC.
But I have no figures for the esters.