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Does Cannabis have chiral molecules? (Chemistry question.)

Discussion in 'Science and Nature' started by Windex83, Sep 10, 2012.

  1. #1 Windex83, Sep 10, 2012
    Are any of the cdb or thc molecules chiral?

    Chiral - In chemistry, chirality usually refers to molecules. Two mirror images of a chiral molecule are called enantiomers or optical isomers. Pairs of enantiomers are often designated as "right-" and "left-handed". [From Wiki]
     
  2. #2 Brenjin, Sep 10, 2012
  3. #3 Windex83, Sep 10, 2012
  4. #4 chiefton8, Sep 10, 2012
    THC:
    [​IMG]

    CBD:
    [​IMG]

    Those hydrogens that have either a bolded bond or a dotted bond connecting them imply that carbon is a chiral center. So yes, THC and CBD are chiral molecules. I'm not too familiar with all the other derivatives of THC and CBD, but my guess is that they too are chiral. All you have to do is look at each carbon and ask if that carbon has 4 different substituents attached to it. If it does, then it is chiral.

    As a general rule of thumb, most molecules made and recognized by nature have chirality as chirality ensure specificity. This is one of many ways in which enzymes distinguish between different substrates. Proteins themselves are chiral. As is DNA.
     
  5. #5 CosmosYEM, Sep 12, 2012
    also, to my knowledge, all life as we know it uses left handed amino acids.
     
  6. #6 Windex83, Sep 12, 2012
    Last edited by a moderator: Sep 12, 2012
    What im trying to ask is

    From website:

    "Would you like spearmint or caraway flavor? That's a strange choice, but believe it or not, they are the same thing. Well, almost. Spearmint and caraway both contain a molecule called carvone with the empirical formula C10H14O, or rather 10 carbon atoms, 14 hydrogen atoms, and 1 oxygen atom. The thing that makes them taste different is that one is left-handed and the other is right-handed. In order for something to have a left or right-handedness, it must be chiral."

    Does cannabis have anything like a taste or a smell that is chiral? Are there any cbd's that are chiral and heal in different ways because of it?

    Hope that clarifies some.


    http://www.scienceiq.com/Facts/YourNoseKnows.cfm
     
  7. #7 chiefton8, Sep 14, 2012
    I hear what you're saying. You definitely have good precedent for asking that question. Many times in the pharaceutical industry, one chiral molecule will be completely inactive while its enantiomer will be biologically active.

    As for cannabinoids, a quick google search found this book: "The Medicinal Uses of Cannabis and Cannabinoids" By Geoffrey William Guy, Brian Anthony Whittle, Philip Robson.

    On page 118, they note that the cannabinoid receptors respond differently to agonists differing only by chiral centers. This article (non-peer reviewed?) also makes similar claims.

    As for what the different pharmacological effects are between stereoisomers...I'm not sure and I would venture to say nobody really knows at this point. A good place to do some research I suppose. :)
     
  8. #8 Carl Weathers, Sep 15, 2012
    Last edited: Sep 15, 2012
    http://www.who.int/medicines/areas/quality_safety/4.2DronabinolCritReview.pdf

    So yes, CB1 receptors are stereospecific. Chances are the cis isomers are even less active, and you can consider (-)-trans-delta-9-tetrahydrocannabinol as the THC.
     

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