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FIDE (the governing body of international chess competition) says here:

The most relevant banned substances for chess are:

• Amphetamines – e.g. Adderall, Ritalin

(...)

Image:

enter image description here

I think either Ritalin should be in a separate category called methylphenidate or Adderall and Ritalin are categorised under 'stimulants (that you need a prescription for but don't have)' (then you can add vyvanse, desoxyn, concerta, etc) or something because afaik Ritalin/Concerta/Methylphenidate is not an amphetamine.

Or am I wrong: is Ritalin/Concerta/Methylphenidate actually an amphetamine?

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I agree that the regulation is worded inappropriately, and that methylphenidate is not an amphetamine. However, I would like to provide a more thorough answer than "rxlist.com says so". We'll have to borrow a few ideas from organic chemistry.

Amphetamine is a substance with a specific molecular structure, shown below (under the title "Adderall"), and an amphetamine is any of many substances with molecular structures based on that of amphetamine (examples in the second image). You can think of amphetamine as the parent structure of a class of substances which are called substituted amphetamines or simply amphetamines. For instance, if the group of atoms circled in blue on the methylphenidate structure was placed on the amphetamine structure, you would have a substituted amphetamine ("an amphetamine").

enter image description here

Methamphetamine, MDMA, ephedrine, methylephedrine and pseudoephedrine are also amphetamines in this sense. I've highlighted in green groups that are added to amphetamine to produce some of these amphetamines.

enter image description here

So, why isn't methylphenidate an amphetamine? The blue group doesn't make a difference, because adding it to amphetamine would just produce a substituted amphetamine. It is the group of atoms circled in red that matter. You see, amphetamine is a portmanteau of alpha-methylphenethylamine, which signifies that amphetamine is a phenethylamine molecule with a methyl group (CH3) in the alpha location, as depicted below. (Phenethylamines are an interesting class of molecules in their own right, including many drugs and neurotransmitters such as dopamine, norepinephrine and adrenaline.)

enter image description here

The group in the alpha position is crucial to our question. If the group at the alpha position is not CH3, then the molecule is not an amphetamine. In methylphenidate, the group in the alpha position (circled in red) is a chain of four carbon atoms (and their associated hydrogens) which may be represented as CH2-CH2-CH2-CH2 (and happens to connect to the N atom at the far end, though this doesn't matter for our purposes). Since methylphenidate has a 4-carbon chain in the alpha position of its molecular structure, it cannot be called an amphetamine, because as mentioned in the previous paragraph the am implies there is a 1-carbon (methyl) group in the alpha position.

enter image description here

Despite this, methylphenidate and amphetamine do have a lot in common. They both belong to the functional class of CNS stimulants, as the OP and the other answerer are aware. In addition, methylphenidate and amphetamine do both belong to a common structural class, which is the phenethylamine class. That is to say, both methylphenidate and amphetamine are (substituted) phenethylamines.

Therefore, one way in which the chess WADA policy could be reworded is:

Phenethylamine Stimulants - Ritalin or amphetamines such as Adderall, ephedrine, pseudoephedrine or methylephedrine, when exceeding the urine concentrations listed below.

Using the category phenethylamine stimulants would be scientifically correct and provide a useful contrast to the category of non-prohibited stimulants, i.e. caffeine.

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    Chemistry is not a strong point of mine, but comparing the structures of Ritalin against Adderall, is the fact that the point in the structure where there is NH2 in Adderall is not NH2 in Ritalin another pointer to the fact that Ritalin is not an Amphetamine? Dec 26 '21 at 9:09
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    @ChrisRogers Good thinking. Having NH instead of NH2 will not exclude a substance from being an amphetamine, as can be seen in the structure for methamphetamine. Indeed, even if the were no H atoms on the N at all, a molecule could still be an amphetamine (which is the case for methylephedrine, structure not shown in my answer). Dec 26 '21 at 17:37
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    I didn't see that with methamphetamine. Thanks for the pointer Dec 26 '21 at 18:46
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    Wow, excellent answer! Would have upvoted twice if I could. Thanks for going into such great depths to provide a most fundamental explanation.
    – Don_S
    Dec 28 '21 at 7:58
  • thanks electronpusher! to electronpusher and @Don_S , in chemistry se orthocresol♦ said similar but electronpusher has a suggestion for FIDE. yay!
    – BCLC
    Jan 13 at 1:18
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The Adderall vs. Ritalin page on Rx List gives the answer.

Both Adderall (amphetamine and dextroamphetamine) and Ritalin (methylphenidate) are central nervous system stimulants used to treat attention deficit hyperactivity disorder [ADHD].

Methylphenidate (also sold as Concerta) isn't an amphetamine and its effects tend to be milder than those of Adderall. Patients also report a more pronounced effect on cognitive function and thought processes when taking Ritalin as opposed to Adderall, which comes with a number of effects on the body such as increased heart rate and others.

I would imagine that the reason for it to be banned in chess is that

Ritalin may help increase attention and decrease impulsiveness.

Therefore, it could potentially create an unfair advantage to those who are under the influence.

However, the World Anti Doping Agency (WADA) do have Therapeutic Use Exemptions (TUEs). This allows those suffering from ADHD for example, to continue their medication therapy as long as they satisfy strict criteria. (See the USADA webpage for more)

Athletes with ADHD can continue using necessary prohibited stimulant medications while competing in sanctioned sports as long as they receive a Therapeutic Use Exemption (TUE), which requires them to demonstrate that they can satisfy strict criteria for TUE approval.

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  • thanks Chris Rogers! everything after the 1st quote i don't really care about. why did you add it though?
    – BCLC
    Nov 29 '21 at 16:07
  • @BCLC - because your question has a clipping saying that Ritalin is a banned Substance under World Anti Doping Agency rules and I wanted to point out that there are exceptions to those rules Nov 29 '21 at 16:09
  • actually i read ritalin isn't an 'exception' although you can apply for an 'exemption' for it or something. under this idea, technically saying 'saying "ritalin is banned" is false because if you have ADHD then (...)' is false because 'banned' already includes the exemptions. or is 'ritalin is banned' actually false?
    – BCLC
    Nov 29 '21 at 16:12
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    @BCLC it is banned as a performance enhancing drug. Some people have been known to take it without a medical need to. " In virtually every sport or activity, improved attention or focus has the potential to increase an individual’s performance. With that in mind, the use of stimulant medication for a lack of attention or focus after an ADHD diagnosis requires an extremely high level of scrutiny in accordance with best clinical practice to avoid abuse in sport." [Source: USADA link in answer] Nov 29 '21 at 16:26
  • ah yes we defeated the nitpick with another nitpick. mwahaha. thanks Chris Rogers!
    – BCLC
    Nov 29 '21 at 17:30

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