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DEA revision of 'positional isomer' definition in Analog Act

trypt

trypt

Bluelighter
Joined
Apr 2, 2004
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I happened across this document a few days ago: DEA notice of propsed rulemaking. It looks like the DEA's response to the recent hike in "research chemical" use. They're trying to revise the Analog Act to make it clear exactly what an analog is, specifically what a "positional isomer" is. I was wondering if some of you chemistry folks could take a look at the "Proposed Criteria That Will Apply to Positional Isomers" section, and see if they are targeting RCs with this amendment, and if so, does it look like they've covered every RC well? They give some examples of substitutions that would be covered under the new, amended analog act: tert-butyl to sec-butyl, methoxy and ethyl to isopropoxy, N,N-diethyl to N-methyl-N-propyl, or alpha-methylamino to N-methylamino. I can tell at least all the 4-ho-T's are covered (because of 4-ho-dmt's scheduling; n,n-dimethyl -> n,n-dipropyl, etc). I'm specifically curious if you can tell whether the fly/dragonfly compounds would be covered under these new rules...
 
I only had time to skim through it, but it looks pretty amusing. It seems that it'll schedule things like MiPT as a positional isomer of DET, and lots of other sorts of bizarrities...
 
It's not covering positional ismoers really (like moving a methoxy group in TMA to give TMA-2), they seem to be propsing something akin to the UK Misuse of Drugs Act derivatives paragraphs (for phenethylamines & tryptamines). In the case of N,N-diethyl to N-methyl-N-isopropyl, they're moving the position of a methyl group, but that isn't actually a positional isomer as such as the actual functional groups are being altered - according to their incorrect chemical terminology just about anything with the same empirical formula (like the empirical formula of amphetamine is C9H13N) could be covered.

What they're proposing will definitely cover things like 5-methoxy AMT being a positional isomer of bufotenine
 
Yeah, 'positional isomer' doesn't really make a whole lot of sense given their definition... 'Positional analogue' would probably be better, and subject to a lot less scientific scrutiny in court.
 
Thanks for the heads up trypt, you should come around here more often.
 
An insightful comment from another forum:

Of course if the motive here really is to plug holes in the analogue laws, I'm sure we'll see some further regulations coming soon.
Click to expand...
 
If they really wanted to close down all the loopholes (well just about) it would be easy enough to use the 1977 amendment (Modification order) to the Misuse of Drugs Act - that's the one that contains the derivatives of tryptamine & phenethylamines paragraphs. It covered most of the compounds carried by vendors (much to the horror of a lot of UK residents) and isn't so fucking vague as the 'analogue act' which is an atrocious piece of legislation, especially when the DEA seems to have tame chemists that are willing to commit perjury & clain things like salvinorin A is an analogue of THC (which is so obviously isn't, it's not even funny to claim it is).

Why don't they go all the way and say,"whatever we decide is an illegal drug automatically is illegal and subject to prosecution"? Oh wait, that's what the analogue act was for in the first place, just they got upset that some chemists wouldn't shut up about things like salvinorin A
 
BilZ0r said:
Thanks for the heads up trypt, you should come around here more often.
Click to expand...
I lurk ADD all the time. This was the first opportunity I had to post something %)

Also, if anybody cares and/or thinks it could help, you could always email the DEA about this proposal: [email protected] before July 24 (or you could write them; more info is provided in the first few paragraphs of the proposal). I'm just afraid that there's really nothing to write that could prevent the proposal from going through.

Out of curiosity, it looks like Nichols' (D)FLY compounds would still be uncovered, right? The proposal is admittedly vague, but I don't think any current schedule I or II chemical has a structure (relatively) similar to the FLY's, even considering the rules in the new proposal...
 
looks like anything with a 5-meo will be gone, along with a lot of others, correct me if im mistaken
 
This is proposterous! So what everything is gone now? I suppose ordering any research chems online is pretty much a crap shoot now, or could it be done without seizure and prosecution? Are all research chems pretty much illegal now?
 
Keep in mind, the Analog Act does not apply to situations in which the chemical in question is not intended for human consumption. In theory, if the feds can't prove that you (or any other human) were intending to use the hypothetical RC, they can't press charges. Unfortunately, it seems like judges tend to side with the gov't when deciding whether a chemical was intended for human consumption, so you can never really be safe.
 
The addition of a definition for the term ``positional isomer'' as
it applies to 21 CFR 1308.11(d) will assist legitimate research and
industry in determining the control status of substances that are
isomers of Schedule I hallucinogens.
Click to expand...

... how thoughtful of them. When what they are really doing is going to make research with these chemicals a pain in the arse. Making substances schedule 1 will deter legitimate researchers because of all the crap they have to go through to obtain and store the substances.
 
The paper said that a positional Isomer must have the same Molecular Formula

" (2) Have the same molecular formula and core structure as a
Schedule I hallucinogen;"

So if for example 4ho-mipt is not a positional Isomer of Psilocin right?I always thought a isomer MUST have the same Molecular Formula.
I see how 5meo-amt is covered as 5oh-dmt, But it sounds like 2c-e, psilocin analogues are still okay, correct?
 
You're right. This proposal won't actually do much at all other than open "room for interpretation." It is just a very feeble attempt to schedule everything in PIHKAL and TIHKAL.

I mean positional isomers??? Come on ... 5-meo-dmt is a positional isomer of 4-(4-Ethylpiperazin-1-yl)benzaldehyde, AMT becomes the same as 5,5'-Dimethyldipyrromethane. Neither of which are even remotely related to scheule 1 substances. This is some seriously bogus legislation.

Oh, wait ... it has to have the same "core structure?" Is this a contest to make the most convoluted piece of legislation ever proposed? If so, I am very impressed.

They definitely missed out on the halogen substitutions. That will be added later of course. And ohhh, they mentioned salts but forgot to put esters of the 4-substituted tryptamines. Maybe it's just easier to sneak in little pieces of legislation at a time vs. a comprehensive set of laws all at once.

Edit: This doesn't even cover 4-ho-mipt or any other 4-pos tryptamines, since 4-ho-dmt is the only one already in schedule 1 and none are positional isomers of it.

Why didn't they just name the compounds, since this really only covers a few?
 
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Actually that is not necessarily correct, pay attention to the “except that” language:

“…except that
(4) Rearrangements of alkyl moieties within or between functional
group(s) or substituent(s), or divisions or combinations of alkyl
moieties, that do not create new chemical functionalities or destroy
existing chemical functionalities, would be within the definition of
positional isomer (and therefore be controlled).”

“Examples of rearrangements resulting in
compounds which would be positional isomers include, but are not
limited to: tert-butyl to sec-butyl, methoxy and ethyl to isopropoxy,
N,N-diethyl to N-methyl-N-propyl, or alpha-methylamino to N-
methylamino.”

Depending on how broadly this is read it might only apply to something like DOM / 2C-G. Or if the “except that” is read in conjunction with the language elsewhere that states that DEA still has the final say in making determinations as to what is controlled, it could be extended to include other compounds.

At any rate this is not the big change yet, it is only a windsock pointing which way things are blowing…

Dondante said:
Why didn't they just name the compounds, since this really only covers a few?
Click to expand...

Because they are trying to broaden their powers without having to bug the Congress who is busy fighting a war on terror by trying to ban gay marriage and flag burning; clear and present threats to the empire. But once they are done poking the free speech and lavender crowds they will get back around to bashing stoners. When they do it will be big, it will be comprehensive, and it will be outdated 5 minutes later when Shulgin’s next book hits the shelves.

I B
 
This isn't a new law or even a proposal for one. It's merely a clarification of language which has been in the CSA for years---namely the definition of "positional isomer" as declared in Chapter 21 of the US Code:

(14) The term "isomer" means the optical isomer, except as used in schedule I(c) and schedule II(a)(4). As used in schedule I(c), the term "isomer" means any optical, positional, or geometric isomer. As used in schedule II(a)(4), the term "isomer" means any optical or geometric isomer.
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This isn't even part of (or reference to) the analogue act. All this "rule" would do is spell out in technical terms that, yes, they did actually mean positional isomers in the technical sense when they wrote that legislation. That is a legitimate definition of positional isomer.

It's debatable whether this rule going into effect would change anything for a person being prosecuted under that section. The DEA claims that no new substances will become scheduled as a result of the rule and that this has been their position (no pun intended :p ) the whole time. They even specifically list some substitutions which are not positional isomers.

Just to reiterate, the "positional isomer" clauses have been in the law for a long time and are in addition to (and may even predate) the haziness set out by the Analogue Act. All this rule would do is lessen room for interpretation of this term in dealings with the DEA---in a criminal proceeding, it would still be up to a court to decide if the DEA is in line here.
 
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So can I or can't I finish my cup of coffee without worrying that it is an amphetamine analog?
 
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