THC isomers and reactions products, CBN, Delta 8, 9 and 10, HHC

by brblog on November 8, 2018

THC Oxidation to CBN

CBN is the oxidative degradation product of THC. It is more stable than THC due to its conjugated structure.

THC Delta 9arrowCBN -New double bonds-Hydrogens lost here

       THC- Delta 9                                                     CBN –New double bonds-Hydrogens lost here

The change is the aromatization of the top ring. 4 hydrogen atoms are lost, and two new double bonds are formed. Creating a double bond where there were hydrogens is an oxidation process, where as adding hydrogens to a double bond is a reductive process. Radical oxygen is responsible for the atmospheric degradation of THC to CBN. There are other chemical processes to synthesize CBN from THC as well.

THC Reduction to HHC

THC Delta 9arrowHexahydrocannabinol (HHC)

     THC Delta 9                                                                          Hexahydrocannabinol (HHC)

Hexahydrocannabinol has a saturated (full hydrogen capacity, no double bonds) top ring. In this sense, it is the opposite of CBN. CBN is oxidized THC and HHC is reduced THC.

THC Delta 9 Isomerization to Delta 8 and Delta 10

THC Delta 8

THC Delta 8, Double Bond is between 8 and 9

Delta-9, the most common and the natural form of THC, is actually the least stable.

Delta 8 has the double bond in a more thermodynamically stable position, and delta 10 even more so due to its conjugation with the bottom aromatic ring.

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15 Comments

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  • Informative.

    Only part that seems off is this “CBN is oxidized THC and HHC is reduced THC”

    Is it still even Thc with a hydroxy group instead of a methyl group at the 11? ??

    • Oops, that is definitely a different molecule than I meant to show. There should just be that methyl group on the top ring and not the hydroxy. Thanks!

  • It would definitley be a diol of some sort..

  • Sounds interesting.

  • […] [7] THC isomers and reactions products, CBN, Delta 8, 9 and 10, HHChttps://brinstrument.com/blog/cannabis-distillation/thc-isomers-and-reaction-products/ […]

  • I learned in Biology that delta 9 THC is the only one that breaks down in your system without leaving free radicals and that all other thc is basically giving everyone cancer.

    • I don’t think that is true. At least the part about radicals.

      CBN is so stable, that is how we know when ancient people used THC. And THC is physiologically safe enough that a lethal dosage is not measurable (in rats).

      Now if you want to talk about side products that people are not properly removing or more exotic and unstudied isomers, then I might agree with you.

      Check this out: https://en.wikipedia.org/wiki/HU-331

      As with many “medicines”, dosage is key! It might even kill cancer, but that doesn’t make it good for you!

      It comes back to the fact that we need to do way more research!

      -Luke

  • Is Delta-8 thc hetzelfde als CBN?

  • there is an effective, standard SOP for thc conversion to cbn in large scale?

    • Define “large”. Several Kg, yes there are people doing it. Hundred’s of Kg, no, and I don’t think there is enough demand to warrant that kind of production either.

      -Luke

  • Can Delta 8 be reduced to delta 9
    what is the processes for hhc cbn to thc reduction? If so catalysts?

    • If it could, I think it would probably be too expensive to be worth it for any kind of usage.

      If you are talking about from CBD starting material, D9 is a step along the way to D8. You need to have special conditions and stop the reaction at the right time.

      Those are million dollar questions. I honestly don’t know, but probably like Ni/Pd/Pt on carbon.

      -Luke

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