Isomers of controlled compounds

[maumakmak]

I just noticed that 2C-E is an isomer of DOM.
DOM is controlled in most countries due to some United Nations agreement.

Many countries have this sentence at the end of their drug laws:
"...including its isomers, esters, ethers, salts, and salts of isomers"

If I understand this correct, 2C-E would be illegal in all countries that have the above sentence included in their drug law and are part of the United Nations, right?
That would then also include compounds like Methedrone (isomer of MDMA) as well as the much anticipated 5-Methyl-MDA (also an isomer of MDMA) and probably also a bunch of others that are currently considered to be legal in many countries.

Is this correct or is there some flaw in my logic?
After all it seems that people always seem to check if the compound is listed in their national drug law, but never check if it is an isomer of a controlled compound....

 

[MagickalKat777]

LOL - hell, 2C-E is a direct analog of 2C-B... seriously if they wanted to prosecute these analogs, isomers, or anything else they feel threatening they totally could.

All of the halogenated 2C's are literally just a single modification from 2C-B....

 

[maumakmak]

Well, in Europe we don't have analogue laws, so the analogues don't matter and therefore the connect to 2C-B is not a problem, but we have this isomer shit and it seems that a lot more compounds could be considered illegal than people actually think

 

[MagickalKat777]

People are fooling themselves if they think the government can't prosecute any substance that they choose to... These are the risks that we take. Luckily they don't usually go after the users but the distributors.

 

[vecktor]

isomer refers to optical and geometric isomers not to positional isomers otherwise anything with the same molecular formula would be covered which is not what was intended.

this has nothing to do with analogue acts.

 

[maumakmak]

isomer refers to optical and geometric isomers not to positional isomers otherwise anything with the same molecular formula would be covered which is not what was intended.

This is also what I thought the original intention was, but the problem is, that it is not clearly defined anywhere (at least not in the german and austrian drug law).

The definition of isomer based on wiki is
"In chemistry, isomers (from Greek ισομερης, isomerès; isos = "equal", méros = "part") are compounds with the same molecular formula but different structural formulas."

So could a person still be prosecuted by that isomer definition (same molecular formular) if it does not clearly say in the law that only optical and geometrical isomers are intended to be covered or would that not hold up in court???

 

[MagickalKat777]

It depends on the judge, how good the prosecution is, and how good your attorney is...

 

[<pyridinyl_30>]

The law is poorly, poorly written. For example, pseudoephedrine is a structural isomer of para-methoxyamphetamine, but it's available at any pharmacy or truckstop.

 

[mad_scientist]

^^^

Vecktor and maumakmak are both right in a way: certainly the definition of "isomer" in this context was only supposed to encompass optical and geometrical isomers (so e.g. ephedrine is an isomer of pseudoephedrine and 3,5-dimethoxy-4-methylamphetamine is an isomer of DOM)

This is obvious, as otherwise for instance isopropylbenzylamine would be considered an isomer of methamphetamine and hence illegal (both are C10H15N), which it is generally held not to be due to the fact it is inactive as a stimulant.

However on the other hand it is correct to note that there is nothing in the law of any country I'm aware of that specifically excludes positional isomers from the definition, and with two compounds like 2CE and DOM that have similar effects as well as the same molecular formula, I could certainly imagine some zealous police prosecutor trying their luck with that argument to see if it sticks. Would not be a good precedent to have set!

 

[<pyridinyl_30>]

What sense does it make to have l-methamphetamine just as controlled as d-methamphetamine when the levo form is totally inactive? According to the law the way it is written, then Vick's inhalers would suddenly be a Schedule II narcotic.

MagicalKat777 is right, though, about the fact that the government could follow the law to the letter if they chose to, which would send the matter to the federal courts and then possibly on to the Supreme Court for clarification.

It seems likely to me that the lawmakers who voted on the Analogue Act had no understanding of organic chemistry, which is a shame. I believe organic chemistry should be taught in high school.

 

[MurphyClox]

isomer refers to optical and geometric isomers not to positional isomers otherwise anything with the same molecular formula would be covered which is not what was intended.

This is also what I thought the original intention was, but the problem is, that it is not clearly defined anywhere (at least not in the german and austrian drug law).

...which is not entirely true! For example does the German BtmG state (more or less) clearly:

Anlage I (for § 1 Para. 1)
Non-Tradeable Narcotics*

- Acetorphin
...
(long list of substances, which ends with)
...
- 2,4,5-Trimethoxyamfetamin

- the esters, ethers and molecular compounds# of all substances mentioned in this list, as far as they are not mentioned in a different 'Anlage' (i.e. schedule list; Note: There are further 2 lists in the German Narcotics Act) and as far as such esters, ethers and molecular compounds# can exist.+
- the salts of all substances mentioned in this list, as far as they can exist.+
[...]
- the stereoisomers of all substances listed in this and any other 'Anlage' if they are intended to be abused as intoxicating agent.

* Note: "Anlage 1" equals more or less Schedule 1 of the US Controlled Substances Act.


# The term 'molecular compound' (translated from the German word "Molekülverbindung") is in my experience a bit unusual in scientific German language. The most common and accepted definition means: Any compound resp. derivative made of covalent bonds. I'm not a lawyer, but I understand this term in the context of this law as 'any covalently formed derivative' (in contrary to any ionic derivative, but these were of course already with the phrase "...any salt..."). This excludes regioisomers, but (theoretically) includes for examples amides, carbamates, cyclic derivates, the famous beta-keto-derivatives and so on; everything that can be formed from a scheduled drug by adding covalent bonds. Sounds at first sight like one of the broadest "analogue laws" worldwide to me if applied literally, but AFAIK is such a broad, literal application of the term not current practice. No idea what the inventor of this term originally meant though...

So well, apart from that special phrasing, the kind of illegal derivatives are quite unambiguously defined. And fortunately, the phrasing is not nearly as broad as its equivalent in the UK, US or Australian law. The term "isomer" is used only in the context of stereoisomer, and even here it applies only if the respective stereoisomers are intended to be used as recreational drugs. If you for example simply intend to gather a collection of rare compounds without ever aiming at ingesting them, you would be still on the legal side. BUT: Any trace of the forbidden isomer as an impurity present and you are fucked. Also might it get difficult to persuade a judge that this (stereo)isomer in your possession was really not intended for consumption but something totally unrelated. Well, in practice the court has actually to prove first that you had such an intention and then you need to demonstrate the opposite, but I'm afraid that any clever prosecutor won't have a big problem with showing this.
It's just this term 'molecular compound' that is causing headaches to me...
And by the way, the phrasing at the end of 'Anlage 2' & '3' is almost identical. At least no further ambiguous phrases!


+ These additional phrases are particularly ridiculous, because they say literally that certain derivatives are prohibited as long as they can exist (the original phrase says "...and as fas as the existence of such esters, ethers and molecular compounds is possible"). Aaaaah yeah, here we have one unique chance to witness proverbial German correctness: German law does not allow something to be prohibited if it can not exist at all.



Peace! - Murphy

 

[maumakmak]

...which is not entirely true! For example does the German BtmG state (more or less) clearly:

Thank's for pointing that out, so it seems that I was wrong on the german law.
However for the Austrian law it definitely only says

"the isomers,esters, ethers, salts and 'molecular compound' of all narcotics listed in section XY" without giving any information what the term isomer is refering too.

However with a law that is based on making single compounds illegal by naming them directly one could definitely argue that it is only refering to optical/geometrical isomers and not to compounds with the same molecular formular as this would then go into a completely different direction than the law is obviously designed/intended for.

 

[MurphyClox]

Yes, but despite my lenghty text do I still agree with what you suggested earlier:
It's one thing what we interprete either out of the term "Molekülverbindung" or "Isomer", but lacking any definite and authoritative definition in the concrete wording of the law, it could have a different meaning in a courtroom. The phrasing is indeed not clear from a judicial point of view.

I wouldn't rely solely on common sense or usual chemical praxis when the stakes are as high as e.g. a prison sentence.


Peace! - Murphy