For those whofollow our bizarre concoction of drug laws, itshould come as no surprise that theyare both ineffective and also woefully ill-equipped to keep up with new (sometimes) legal analogs that even a marginally trained chemist can do. As I wrote about fentanyl analogs, chemistry, specificallysynthetic organic chemistry (1),can easily be used toget around the law.
Rather than bore you with a tome about the legality of marijuana and marijuana chemicals, I thought I'd bore you with a chemistry lesson instead. Get ready. Here it comes! It's been a while, so I made this one especially incomprehensible. Let TDCLFH begin!
Nomenclature - The bane of our existence
Chemistry nomenclature, the tedious process ofnaming chemicals, is a baffling array of multiple naming systems,dozens of different names for the same chemical (2),and incomprehensible rules.This can be illustrated quite "nicely"by looking at how delta-8 THC, a chemical that has recentlybeen in the news, gets its name. Thisshould give you a pretty good idea of why nomenclature drives chemists nuts. (For clarification, you should know that delta-9 the primary THC isomer in marijuana is commonlyknown as THC. The namesare interchangeable)
What Does the 8 in Delta-8 Mean?
If you have any propensitytoward anxiety or self-harm, you might want to skip this. The figures below show the (apparent absence of) logic behind the number 8. Figure A (left) starts off making at leastsome sense.
Each carbon is assigned a number, which is necessary for assigning a name to aunique structure. The carbonatomat 12:00, which is attached to a hydroxyl group (green square), is called#1. From there, proceedingcounterclockwise, the numbers assigned to the next carbon atomsincrease logically 2, then 3, then 4.Then 5, right? Nope.
Figure B shows that the position after #4 is ...#10b (blue). Huh? How can this be? Answer: you don't want to know. Continuing, #5 gets assigned to the oxygen atom next to 10b.No big deal. We're still pretty much followinga backward clock, so there is some logic remaining. But notmuch.
(Mercifully ending this wretched lesson)Figure C shows thatthe carbon atomafter #6, like #10a, makes no sense. Instead ofbeing called#7, it's6a (blue). Why? Once again, don't ask. A degree of sanity returns after this. Carbon #7 shows up next on the clock dial (4:00) and is followed by 8 and then 9. This is where the "delta-8" comes from. Greek letters are usedto describe the position of double bonds (yellow line). The same holds true for dietary supplements,for example, omega-6 or omega-3 fish oils. Delta-8 means that the double bond exists between carbon atoms 8 and 9. The delta part is beyond the scope of this article. Be thankful for this.
And, if this wasn't sufficiently horrifying to have you opening up Amazon to order Final Exit, it can be worse. There is a 69-page document put out by the WHO titled "Isomers of THC."If you're looking for a little light readingthis is as good as it gets. Take a look at this especially enthrallingpassage:
Ah, chemistry. Source: WHO,Isomers of THC
Seriously, who cares?
Both marijuana users and law enforcement care, otherwise I would not have dragged you through this hideous exercise. The position of that double bond determines both the pharmacological properties and legality of the chemical. The chemical properties of delta-8 and delta-9 THC (the "normal" THC in marijuana) are nearly identical, as aretheir chemical structures. The only difference in strucrture is the position of the double bond (yellow).
As you'd expect, when two molecules are so similar theyact similarly on the receptors inthe brain. This is largely true, although there are subtledifferences between the two. Delta-8 has a similar psychotropic profile to THC but is thought to be less potent. Relatively little is known about this drug because itarrived on the scene only recently and becausecannabis and CBD oil contain only trace amounts of the chemical, so there wasn't enough around to isolate and study until a chemist figured out how to make it.
Chemistry to the "rescue"
Two years ago I wrote about the chemical differencebetween CBD and THC onechemical bond and whether it was feasibleto use CBD as a source for THC. (It isn't the reaction that was used gave a mess (a complex mixture containing many impurities).
HPLC trace of psychoactive substances formed by reacting CBD with dilute acid. There are at least four impurities present. Source:Cannabis and Cannabinoid Research Volume 1.1, 2016 DOI: 10.1089/can.2015.0004
But the chemistfound that a different setofconditions enabledCBD could be converted not to THC, butto delta-8 THC, which spawned a cottage industry in the stuff(3). Thischemistry is explained on the subtly named site Hempvada. Why do I think that their annual board of directors meeting looks something like this?
HempvadaBOD meeting? Photo: Flickr
A quick visit to the Hempvadasite shows (unsurprisingly) that they are peddling CBD products. With a flair! Here are some of them:
Delta-8 was synthesized because it was previously "unknown" and therefore (possibly) legal. Or maybe it isn't. This depends on where you are and how drug laws are interpreted. It's a complicated mess.I haven't the bandwidth (or intellect) to go into the myriad of often contradictorylaws governing the use of marijuana and its chemicals, but Jon Jackson writing for Newsweekand Bill Weinberg on the Project THC site doa very nice job of explaining this complex topic.
For all both of you who have made it through TCDHFH as well as the rest of this somnorific article, congratulations! Most humanswould have taken onelook at the nomenclature section alone and hastily switched over to reading prescription drug inserts. Feel free to reward yourself. Perhaps chow down on some pot brownies. Just keep in mind that what you're getting might not be so pure.
An HPLC trace of an extract of cannabis brownies. The damn things have more chemicals in them than the Gowanus Canal. Source: Sigma-Aldrich
(1) Synthetic organic chemistry is the science of converting one substance to another by the use of known reactions. It is the basis of much of drug discovery.
(2) I wasn'tkidding. All of the following are legitimate names for delta-9THC. There are 136 of them. Is it any wonder that chemists are thought of as some yet-to-be-defined, but aberrant species?
(3) Chicago Sun Times: "An unregulated, weed-like drug dubbed CBD on crack has spiked in popularity. Now the legal pot industry is calling for a crackdown."
See original here:
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