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

by brblog on November 8, 2018

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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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21 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

  • There seems to be a huge push to demonize and scare-monger about the process to create D8. The latest are claims that there are large amounts of potentially harmful stereoisomers created along with the Delta-8, and since these have not been tested, they claim a huge risk. Most recently I was shown a link from 3-Chi (producer and seller of alternative cannabinoids) that links to a Lab report from Boulder that alleges untested and illegal isomers along with the Delta-8. I am extremely skeptical of these claims, but don’t have any solid basis other than the fact that they are equating the unknown to a risk. My anecdotal experience has been that it is more stable, consistent, and medically viable than D9, and over the last year or so, there has been a huge public experiment and I have yet to hear of significant issues of any kind. I also realize that this is still anecdotal. Do you have any data to help debunk the fear?

    • The whole situation legally and scientifically is very gray right now. And I will lead with that no I don’t have data.

      The biggest insight I can offer is that many of these processing labs are not properly equipped for their own safety, let alone yours. I have been in many labs and seen the grass on both sides.

      Similar to the black market for flower, smoking a single joint containing pesticides is not going to have long term consequences. Constant or regular exposure is an entirely different story though. I think that while over-regulation will kill the small players, some regulation is definitely needed. Has anybody died or developed serious complications in the past two years? Not that anyone can prove. But kick the can down the road 10 years of using once or more a day and we may be able to better correlate medical conditions with usage.

  • Heya,

    Do you think its possible to convert CBD to CBND with just heat and oxygen? (Similar to converting THC to CBN)

    • Maybe.

      The first problem is getting a good yield. THC + Heat Oxygen does not yield a high amount of CBN for example. Most of the lost THC goes to unwanted byproducts. The second problem is getting a proper analysis done. CBND is definitely not on the standard 10. And if you do find a lab that tests for it at all, the numbers may not be very accurate.

      -Luke

  • Has anyone observed what D8 dose eventually degrade into, I have heard allot of people say D8 degrades to D9. But I cant find any evidence to back that up, I think they may have just got it backwards what are your thoughts?

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