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Isomers make any difference?

Phat_bass49

Phat_bass49

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I know that technically this isn't a cannabis question, but i believe it fits here best, if not, please move it :) thx

Well firstly, are there any differences in effect between delta 1 cis/trans tetrahydrocannabinol? Does 1 of them have a higher affinity for cannabinoid receptors than the other? Do optical isomers have different effects?? I know that some drugs (L-dopamine for example) only work in certain optical isomers so is this the case here, and if so which (L or D) is active?


Thankyou bundles for your help :) :) :)

Edit: if only 1 of the isomers is active, could one grow a plant that produced the active isomer mainly?? Has anyone sequenced the cannabis genome yet :P :)
 
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The trans, levo-isomer of delta-9 THC is the only naturally occuring isomer. I don't know the binding affinities for all of the different isomers, but the people in ADD might.

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Well firstly, are there any differences in effect between delta 1 cis/trans tetrahydrocannabinol? Does 1 of them have a higher affinity for cannabinoid receptors than the other? Do optical isomers have different effects?? I know that some drugs (L-dopamine for example) only work in certain optical isomers so is this the case here, and if so which (L or D) is active?
Click to expand...

Um. where is the cic and trans going to come into it? And THC isn't optically active, so you can forget that idea as well.
 
^My chemistry knowledge is very limited (still in sophomore highschool year) but why do you say that thc has no optical isomers? Do you mean naturally occuring?

I think phatbass was on lycaeum and found this page: http://leda.lycaeum.org/?ID=10812

1) How many isomers are there of the THC molecule?

There is delta-1 THC (using a different numbering system, this is
also known as delta-9 THC). It has two asymmetric centers, and
so it can exist in a trans- or as a cis-form (known as
stereoisomers) and each of these forms is resolvable into a
dextro- and a levo-component (known as optical isomers).
Click to expand...
 
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Maybe I'm just being unobservant, but I can't find them.. Someone point them out for me...
 
Look at bridgehead atoms 6a and 10a(i.e. the ones not involved with the aromatic ring).
 
yup... I'm wrong... I must have been retarded when I looked at them first, I musta been thinking "oh they've got carbons on each side, so it doesn't matter" or something stupid like that.

So, do the optical isomers have different effects, they sure do. Check out Mechoulam's input on this NIDA research monograph Stereochemical Requirements for Cannabimimetic Activity

Specifically the natural (-) (3R,4R)-enantiomer is much more active than the alternatives
 
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^Thanks for that pdf link, learning quite a bit about cannibinoids now.
 
However, according to the Shulgin letter linked above, the plant itself can only produce one isomer.

And, as to your other question, no, the two isomers cannot be
isolated from the plant, as only one is there.
Click to expand...
 
^it would still be possible in the future to grow a plant that would mainly produce one of the other active isomers though, wouldn't it?
 
^ Well in THEORY-- I mean, even if you had access to millions of dollars and the best lab in the world, I doubt mordern technology would allow you, unless there was some freak enzyme you were lucky enough to stumble upon.

I mean, you can only Genetically engineer existing enzymes into a plant, not create new ones, and I don't think you're going to find enzymes which put THC together, just in a different rotation, any time soon.
 
Specifically the natural (-) (3R,4R)-enantiomer is much more active than the alternatives

Well then isnt this just ghey?

Ofcourse when you look at a well known product for the first time its fundamental that we address the question, since the molecule is asymmetric, what is the un-natural isomer gonna do?

I mean shit like that just has to be done, its compulsary.

But when you know that it was an act of God to produce that particular isomer and not just some random occurance in nature then who gives a fuck any more. I mean how ghey is that dude. Totally
 
^ Yeah, it's interesting that the nature isomer is the potent one, it make's me think that THC IS there to act on CB1 receptors.
 
Huh? No I mean, the reason why cannabis produces THC in the way that it does, is so it acts on CB1 receptors, like tobacco produces nicotine to act on insect nicotinic receptors.
 
^ yer i was thinking that the best way for a plant to stick around (i.e NOT die out) is to produce a chemical (or chemicals) that is/are important to humans/other animals because we're gonna want the plant and therefore grow/keep it. lol It's probably not like that just a nice thought.

It is strange that of the 4 possible isomers of THC cannabis only produces the active one, it makes you wonder if perhaps other isomers of other (non-active) naturally occuring chemicals would be active?
 
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