The Mayfield Mess: Distinguishing Meth from Legal Drugs

C’mon, will Chad Knaus please push the limits of the gray area so that I can write about something other than drugs? But that’s the big news (again) this week given that someone leaked that the drug Jeremy Mayfield tested positive for was methamphetamine.

Amphetamine (C9H13N) is a psychostimulant. Methamphetamine (C10H15N) is an even more powerful psychostimulant. Standard tests usually test for the general class of amphetamines (which includes meth). For example, the Federal government guidelines require that companies requiring commercial class drivers licenses clear their employees for the “SAMHSA-5” the Substance Abuse and Mental Health Services Administration. So most drug testing companies’ basic test covers:

  1. Cannabinoids (marijuana, hash)
  2. Cocaine (cocaine, crack, benzoylecognine)
  3. Amphetamines (amphetamines, methamphetamines, speed)
  4. Opiates (heroin, opium, codeine, morphine)
  5. Phencyclidine (PCP)

A lot of the amphetamine molecules look very similar to neurotransmitter molecules that occur naturally in your body, like epinephrine, norepinephrine, and dopamine. Methamphetamine and amphetamine have an interesting property: They have enantiomers. Long word, but don’t panic. Put your right and left hands in front of you backs of your hands toward your face. They are mirror images of each other. There’s no way that you can rotate your hands so that they line up exactly on top of each other (meaning that both backs still face you). Meth is the same way. There are two versions of it.

l-methamphetamine (an abbreviation for levomethamphetamine) is on the right in the picture above. l-meth is the active ingredient in inhalers like Vicks. (This is why Mayfield was asked specifically if he had used Vicks. The other form dextromethamphetamine or d-methamphetamine is what we know as meth.

When methamphetamine gets to the brain,it triggers the release of of dopamine, serotonin and norepinephrine, the feel-good neurotransmitters, which is why it induces such a powerful feeling of euphoria — and why it is so highly addictive. Meth is often smoked because you get more of the feel-good molecules into your body that way (90.3% bioactive via smoking vs. 60.2% orally).

Here’s why the presence of two versions of the same molecule is important: If you take meth, it’s entirely d-methamphetamine. A number of other drugs contain molecules like pseudoephedrine, which are metabolized by the body and can produce amphetamine.

For example, famprofazone, an over-the-counter med that’s found in some pain medications, produces equal amounts of the d- and l- forms of meth and amphetamine when it is metabolized in the body. So if the meth that is detected is due to use of this drug, then there should be comparable amounts of each version of the molecule.

The use of something like Adderall or Claritin-D that could produce amphetamines in the urine as a byproduct would produce both types of molecules, which leads me to wonder whether the reason Dr. Black said that there was “no way” the combination of the two over-the-counter medicines could have produced the result they saw is because they detected only the d- version of amphetamine molecules and the over-the-counter medications would have produced both l- and d- versions. (And if you used Vick’s, you’d find only the l-version.

Needless to say, tests beyond the basic five are required to detect the enantiomers. The two molecules have the same mass – they’re just shaped differently. The shape means that they attach to other molecules differently, so you can distinguish between them by seeing how they react to other molecules. Current tests are very sensitive, allowing testers to rule out prescription drugs as the source of the positive results.

More as it develops, but I really am making a plea to Chad to come up with something really creative so that the next entry is about racecars and not this.

30 thoughts on “The Mayfield Mess: Distinguishing Meth from Legal Drugs”

  1. Nascar is a lot like our present government, control freaks. I’m not sure what Mayfield did or did not take, but I do know he will most likely be made an example of by Nascar. Remember Nascar is never wrong, but if they are they just change the rules.

  2. Your hope is for another big story line to come along.

    My hope is that when this mess is finally sorted out. Jeremy owns NA$CAR. Then maybe it could get back to being NASCAR, & become more about racing, less about $$.

  3. Thanks for a great article and for including graphics. Your explanations are probably the type that NASCAR will use in court.

  4. Thanks for clearing this up Diandra looks like NASCAR have an incredibly strong case against Jeremy.

    On a lighter note could the .017 inch of Carl Longs oversize engine infraction be due to an over heated motor ?

  5. Thanks yet again for another true science explanation of something a lot of folks have talked about and commented on but never fully clarified.

  6. NO MATTER WHAT mayfield took or did not take he agreed to nascars policy. He didnt tell them what medicine he was using and that is a clear violation.

    It is no different than a lot of companies out there if you do not tell them what you take and something shows up your gone.

  7. “Several Drivers Testing Today”? Now drug testing brings a whole new meaning to the phase testing. IE, Tire testing, Track testing, Drug Testing. LOL Just saw some humor there. Seriously, drug testing should have been going on for a long time. Problem was they had to creep into it.

  8. Poor Jeremy mayfield. Only a handful of people know what actually took place, and they’re not talking. That leaves the rest of the world speculating, hypothesizing, and theorizing all sorts of unconfirmed things. I’ll say that again…UNCONFIRMED. The saddest part is that, whether he did or didn’t, he is done in NASCAR. No sponsor in their right mind is going to sign with him, because he’ll forever be remembered as “That Guy”. And without sponsors, image, and money, drivers cannot last in the sport. If you think it’s not true, then test yourself: Dexter ________ drove last week at Pocono during the Cup race. Can’t remember his last name? The prosecution rests.

    As far as crew chiefs “pushing the limits of the gray area”, for those of you who know nothing about NASCAR history, that is how our sport evolves, and the rules get changed, and it becomes more equal for everyone. Have you ever heard of applying a band-aid when there’s no boo-boo? Of course not. The perception at that time is that, since there’s no boo-boo, there’s nothing to fix. So stop poking at crew chiefs for being innovative and creative, while operating within the rules, to give their drivers an edge. That’s what they do. That’s why they’re called crew chiefs, and not tire changers, or fabricators. They make the calls, and they live with the results.

    And that’s Mr. Knaus to you.

  9. OK, so we know from various news sources that he tested positive for 3 things. Claritin-D, Adderall, and something else, which is being reported as amphetamines.

    It can’t be that he only showed the presence of the d-enantiomer, because then he wouldn’t have tested positive for Adderall – according to your final link Adderall is a 3-1 ratio of d- and l-enantiomers, with the d- decaying faster than the l-. So they’d have to be looking at ratios, and the only thing that comes to mind is that the d-/l- ratio was much greater than 3-1.

    Can the psuedephedrine (which appears to be a d- version) cause that? I don’t know, but I know that’s what Mayfield’s lawyers are going to argue.

  10. Skip: You are right, it is the ratios that they would be looking at, taking into account the breakdown of the Claritin-D and the Adderall. A drug lab would have detailed calculations, taking into account how long ago he took the drugs he said he took and what the ratio would be IF those were the only drugs he too.
    It seemed like an easier way to explain without dragging ratios into it.

    And Tom, I happen to think Chad is one of the most creative, smart people in the garage. Every time he does something – legal or not – it gives me the opportunity to address the science of making cars go fast. The problem is that I generally have to wait to talk about the most interesting things until they are either clearly legit or someone gets fined for them. The best innovations are always the ones we never hear about.

  11. If Jeremy Mayfield is completely innocent like he claims to be, why don’t they test him again with the things he claims he was taking and see if the test comes out the same, they would have to make sure he is clean to start with, but what the hell, give him a chance to prove what he is saying to be true, isolate him for a certain amount of days test him again, and see if the test comes out like it did before, if he is innocent it would come out identical to what he tested before. I am a huge Mayfield fan, and will be always. If he says yes great lets do it, and lets just see if what he says is true, give him a chance without the BS, I wish him the best of luck, and Nascar should at least give him this chance to clean this mess up once and for all. This is just my opinion, and an easy out for everyone. GOOD LUCK JEREMY, I will always be your fan!
    Bob

  12. If Jeremy Mayfield is completely innocent like he claims to be, why don’t they test him again with the things he claims he was taking and see if the test comes out the same, they would have to make sure he is clean to start with, but what the hell, give him a chance to prove what he is saying to be true, isolate him for a certain amount of days test him again, and see if the test comes out like it did before, if he is innocent it would come out identical to what he tested before. I am a huge Mayfield fan, and will be always. If he says yes great lets do it, and lets just see if what he says is true, give him a chance without the BS, I wish him the best of luck, and Nascar should at least give him this chance to clean this mess up once and for all. This is just my opinion, and an easy out for everyone. GOOD LUCK JEREMY, I will always be your fan!
    Bob

  13. It would be interesting to see why he was taking Adderal. Adderal is a controlled substance that is used correctly treats individuals with ADD/ADHD. Unfortunately, people take this drug for a high especially in college. If he has ADD/ADHD, then that is understandable why he took it. If he does not, then I would question his intentions.

  14. It’s been 2 years this month since any HMS car has been declared by NASCAR to be cheating. So don’t hold your breath.

    If I were you diandra, I’d look for sumthin’ else to write about instead of Chad cheating, I think he’s learned his lesson after that heavy fine at Sonoma in 07. Oh I know, write about JR and IF the 88 team can turn their season around. So far, not looking so good. The Nation is waiting with bated breath in hopes he can make all the pitstops without messing them up. LOL

  15. Maggie: I know that everyone’s been really above board lately, but I yearn for the ‘good old days’ – when you found out that a crew chief did something and your first reaction was ‘darn, I wish I’d thought of that’, instead of – ‘what the heck was he thinking?’ Or even something like the yaw that NASCAR had to eventually clamp a lid on. Remember when someone on the 48 engineered it so that when you turned the jackbolt, the rear window of the car bulged out, giving it an aerodynamic advantage. That was interesting.
    I’m one of the people who really wishes NASCAR would enlarge the ‘box’ a little and let the creativity of these really smart engineers and mechanics shine.

  16. Bob: Regardless of whether one is a Jeremy Mayfield fan or not, we all want this resolved fairly. There is a lot at stake for both NASCAR and Mayfield. Unfortunately, most of the story is being revealed by leaks and innuendo, making it very difficult for fans to know the facts. I predict it ends up like most NASCAR lawsuits – settled out of court with a gag order.

  17. diandra, fan or not I just think it would be fair to give him a chance to clear his name, or if he is guilty, he is guilty, only he knows this, but IU was just saying that there might be an option, drugs legal or not do different things to different people, and I hope this gets resolved FAIRLY!!

  18. If Mayfield is clean why don’t he get an hair follicle test and present it to NASCAR thru a third party lab. I’m working on a DOT in ALASKA and they test both urine and hair. The people that have tried the shampoo have got busted. The test company test for these doping agents as well. Its worth a shot. It goes back 90 days plus……..

  19. Here’s the thing, once this gets into Federal Court (not some bullshit, “OMG it’s Nascar, I loves me some beatin and bangin fender slappng racin” NC state court), one of the key issues will be the question of what Nascar’s drug policy is and did they inform the drivers?

    They other issue will be the scientific facts and the compounds of Adderall and Claritin D and the question of , “…Have you recently inhaled any toxins (like Vick’s or fumes from a fire–Mayfield’s claim)…

    Once these issues are decided, Mayfield will be exonerated and then he’ll sue Nascar for a ton of money. And make no mistake Mayfield wins this thing in Court.

  20. Does anyone remember Shane Hmiel????
    Jeremy doesn’t have a chance in hell!
    The lab that the test is sent to is in Nashville,the best in the country.They do all the tests for all Major sports.Jeremy is guilty as the day is long.Jeremys poor judgement cost everybody on that team their jobs.Jeremy will have to follow nascars rules to get back on the track,which means that won’t be until next year.How do I know all this??? I was on the Busch team Shane drove for

  21. Mayfield has ADHD and thats why he was (is) taking Adderall given to him by his doctor.
    One question I have is,is the so called Dr.Black a M.D. or just a PHD?
    We may never know the true story after everything is said and done,But I for one can’t believe that Mayfield would take his own cash set up a race team and than do drugs knowing ASSCAR was drug testing drivers.It just don’t add up!

  22. Hey everyone Jeremy knew the rules, but he thinks they don’t pertain to him. Remember, he is a LEGEND in his own mind!!

    He once stated that he made Cale Yarborough what he was then when he drove for him. It is never his fault with whoever he drives for it’s the owners fault not his.

    He’s a washed up has been, who dumped his first wife for a pretty young thing when he got a little popular.

    What a waste!!

  23. Oh, belive me there is more to come. Jeremy is no fool and I would bet that he has retested and you will see those results in court. It’s time that NASCAR stops dictating and gets back to running the sport. Jeremy is a good guy and it was nice to see Carl Edwards stand up for him in the recent article. Jeremy has thrown himself on the sword and the other drivers should be grateful to him, there for the grace of god go I. We all know NASCAR will loose this case but the deal that will come out of this will gag both sides from talking. Go get ‘m Jeremy!

  24. The thing is that the pharma industry will never ever tell you the truth. The know how to manipulate product tests or more nice: how to make them appear in a better light.

    But don’t get me wrong, thank you for the post, it IS usefull.

  25. The truth is, Mayfield will walk on this. Guilty or innocent, it does not matter. The combination of preparations he took will easily leave the “i-” and “d-” markers the tests look for.

    His ADHD medication was supposedly prescribed to him, so he is fine there and the other meds are all legal, over the counter agents that when taken, in varying degrees, will break down into the absolute core components that “meth” metabolizes into.

    Jeremy’s dad was a friend of mine. He built custom motorcycles and was a really good fellow. We lost him not long ago but he was so very proud of his son and Jeremy was always a very fine young fellow.

    There is no way the court can anything but find him not guilty, which will open the doors to the Nascar MONEY VAULT! Then the series may becomes the France-Mayfield company.

    Bill Diehl is a deadly lawyer. Ask George Shinn’s former legal enemy…Diehl asked so many hard questions that the poor person committed suicide at the end of the whole thing. He is not to be tinkered with.

    Bill is considered one of the 3 most intimidating criminal defense attorneys in the southeastern US (BAR NONE)….He may even have JM out of this thing before it even starts.

  26. Both of those molecules are the same. They are just twisted at the c-c bonds. Flip one over and you get the other.

  27. diandra,

    Have you seen this?

    Bubba digested Claritin-D and Adderall, the same drugs Mayfield claimed to have taken, and then took a drug test just as Mayfield had weeks earlier. When the results came in, Methamphetamine showed as a positive just as it did for Mayfield even though Bubba never came within five-hundred miles of the illegal drug.

    Now, one has to wonder, is Mayfield telling the truth or is NASCAR’s drug test flawed? ‘Bubba The Love Sponge’ has at least given NASCAR good reason to take another look at it’s screening process, and he has also given Mayfield some powerful evidence in his quest to challenge the mighty sports organization in a court of law.

    http://whtq.com/blogs/bubba/2009/06/bubba-drug-stunt-shows-mayfiel.html

  28. “…which leads me to wonder whether the reason Dr. Black said that there was “no way” the combination of the two over-the-counter medicines could have produced the result they saw…”

    Because you misquoted what Dr. Black said based on what Jeremy said.

    http://www.nascar.com/2009/news/headlines/cup/05/09/jmayfield.violates.drug.policy/index.html
    What Jeremy actually said,
    “In my case, I believe that the combination of a prescribed medicine and an over the counter medicine reacted together and resulted in a positive drug test.”

    http://www.jayski.com/teams/41.htm
    What Dr. Black actually said, “I have never seen a violation like this due to the combination of over-the-counter or prescription products.”

    NOT two OTC medications. One OTC medication and one prescription medication. The only reason Dr. Black brought up the Vick’s Inhaler to Jeremy and asked if Jeremy used it was to look for another explanation other than meth that could be causing this positive test result.

    Here, try reading this. Maybe it will help you
    https://www.norchemlab.com/main/drug_references/factsheets/amphe_metha.pdf

    With Jeremy’s reported meth level being 48,000 ng/mL and the cut level at 1000 ng/mL…uh I hate to tell you this but there’s a whole lot more going on here than just popping an extra Claritin D.

  29. In response to a blog item on NASCAR’s testing policy I posted a while ago, somebody commented that a NASCAR drug testing policy is hypocritical because burning the fuel creates a chemical change that produces, in his words, “a low grade form of speed.” and that anybody who breathes these fumes, drivers and fans alike, are high on speed because of this. I think the commenter may have been a corn farmer or an employee of General Electric, but I want to know if there is any truth to this.

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