5-Methoxy substituted tryptamines not analogues?

[ssabusivefw]

It has always been suspected that 5-Methoxy substituted tryptamines would be analogues (e.g. 5-MeO-AMT). However the DEA recently (January 19, 2010) explicitly made 5-MeO-DMT illegal by adding it Schedule I. This suggest to be that they didn't feel that they could easily prosecute someone under the Federal Analog Act; if they could it wouldn't be necessary to specifically schedule it. This would suggest that the 5-Methoxy addition makes it different enough from the parent compound, so would this logic then not apply to all 5-MeO, 4-MeO-, 3-MeO, as well as Tweetios? To me it seems like the DEA might just have hurt their efforts on all these compounds under the FAL. Curious what other's think of this?

 

[...]

so would this logic then not apply to all 5-MeO, 4-MeO-, 3-MeO...

just a comment: positional isomers of "hallucinogens" in schedule 1 are automatically co-scheduled, so if they scheduled 5-MeO-DMT they scheduled all MeO-DMTs

The action was taken on 20 DEC 2010. Read Federal Register entry. I'm inferring that they didn't express an opinion on whether or not it qualifies as an analogue of anything. Rather, they establish why it should be scheduled. Example:

5-MeO-DMT is related to the schedule I hallucinogens N,N- dimethyltryptamine (DMT), 2,5-dimethoxy-4-methylamphetamine (DOM), lysergic acid diethylamide (LSD) and mescaline in its pharmacological properties and hallucinogenic effects. In animal drug discrimination studies, DOM, LSD, mescaline, DMT, and alpha-methyltryptamine (AMT) fully substitute for the discriminative stimulus cue of 5-MeO-DMT. In in vitro receptor binding studies, 5-MeO-DMT, similar to DMT and other schedule I hallucinogens, binds to central serotonin 2 (5- HT2) receptors. Anecdotal reports from humans who have used 5-MeO-DMT describe hallucinogenic effects similar to those produced by DMT. 5-MeO-DMT, however, is reported to be 4 to 5-fold more potent than DMT when administered by inhalation, sublingual or oral (if encapsulated) routes of administration.

 

[atara]

The DEA realizes something: Taking actual legal action against analog sellers makes them look bad. Most Americans, by both our efforts and the DEA's, are blissfully unaware of the analog market. I've had conservative friends tell me they thought acid wasn't even around anymore (while I had some in my pocket). The DEA desperately needs to maintain the perception that they are winning the drug war.

Despite this, 5-MeO-DMT is actually a legitimately dangerous compound. There exist plenty of reports of serious adverse effects on Erowid that the DEA knows they really ought to try to prevent the trade in this dangerous chemical, and so they chose to schedule it, instead of more popular RCs like 2C-E, 2C-I, or methylone, all of which are relatively benign. I don't agree with the scheduling, but I do at least understand the reasons for it.

 

[amanitadine]

I think trying to look at the DEA s actions through a rational lens is totally futile.....

 

[MagickalKat777]

I, too, am totally confused why they scheduled 5-MeO-DMT. I don't know many that actually enjoy the experience of that one.

 

[vecktor]

the opinion in the DEA is that scheduling something is better than relying on the analogue act because there is less interpretation and less to prove. Ffor an analog prosecution you need 1, to identify it, 2 to show it is substantially similar and 3 it was intended for human consumption. if something is scheduled all you need to show is that the material seized contains a scheduled drug job done.
This has no relevance to whether the DEA thought or thinks it is an analogue

A lot of lawyers see the analog act as deliberately confusing and its primary function is a deterrent rather than being a piece of law they rely on.

 

[fryingsquirrel]

IIRC someone was actually prosecuted under the analog law for 5meo-dmt and was found not guilty by a jury (likely because they didn't have a fucking clue what the experts were talking about), which lead to it being scheduled.

 

[Transform]

Specifically scheduling means that they do not need to prove that it was for human consumption. Any sales, possession, import etc is totally illegal, making prosecutions easier for them.

 

[Hammilton]

IIRC someone was actually prosecuted under the analog law for 5meo-dmt and was found not guilty by a jury (likely because they didn't have a fucking clue what the experts were talking about), which lead to it being scheduled.

It was either AMT or AET actually, and they were claiming it was an analogue of DMT. Not a huge stretch, but not an obvious leap either. That was back in the mid 90's though, 93 or 94 I think.

I'm not aware of any recent analogue cases.

I think the reason they don't want to try analogue cases is because the legislation is going to be considered unconstitutionally vague eventually, and they can keep it as a deterrent until then.

 

[fryingsquirrel]

It was either AMT or AET actually, and they were claiming it was an analogue of DMT. Not a huge stretch, but not an obvious leap either. That was back in the mid 90's though, 93 or 94 I think.

I'm not aware of any recent analogue cases.

I think the reason they don't want to try analogue cases is because the legislation is going to be considered unconstitutionally vague eventually, and they can keep it as a deterrent until then.

Couldn't AMT be considered not just an analog but a positional isomer of DMT? I mean you're just moving a methyl group. Even though that radically changes the affects I doubt that would much matter to the DEA. I'm aware of the case you refer to, if only because it is mentioned in passing in Pihkal. Anyway, I did some googling and found some obscure forum where the guy who got busted was asking for legal advise. Apparently he sold 5meo-dmt (which he said he extracted from a toad) to an undercover at a festival.

 

[Hammilton]

Couldn't AMT be considered not just an analog but a positional isomer of DMT?

You'll probably have a d'oh moment, but: obviously the answer is no. AMT has one alpha-methyl substitution, DMT has two N-methyl substitutions. AMT could be considered a positional isomer of N-methyl-T, but I don't believe it's scheduled.

That there's another case is possible, and a case like that probably wouldn't make much wind. One that was appealed and reversed is far more interesting, but there are very, very few of these, which makes me think that there are very, very few actual successful prosecutions or you'd have people appealing it on the basis of unconstitutional vagueness.

It also seems that believing it not to be an analogue ought to be a valid affirmative defense.

 

[fryingsquirrel]

You'll probably have a d'oh moment, but: obviously the answer is no. AMT has one alpha-methyl substitution, DMT has two N-methyl substitutions.

lol, yeah maybe I should change my username to Homer Simpson.

 

[amanitadine]

All this talk of trying to find the reasoning behind these things is silly, as reason doesn't play a role in the goings on. I was charged (and convicted) with the manufacture of a controlled substance for a chemical that wasn't scheduled. This was at the state level and not federal. Granted, I had a few other charges for explicitly scheduled items but the non scheduled drug was prosecuted under another charge for manufacture of a similar drug. (it was 2C-C and I was charged with 2C-B). I did plea out however so this didn't go before a jury but I don't think it would have turned out any different. The good cases for the other clear cut charges definitely influenced the odds I was facing, but my extremely expensive and experienced attorney was able to point out a few other cases where "analogs" were prosecuted successfully, and not under the analog act. A jury of your peers isn't often the greatest thing, as my peers are not that bright. A bunch of talk about differing functional groups etc just confuses them, and when the prosecutor gets up there and points out laboratory equipment, chemicals, and how bad meth labs are, you are fucked. This happens, and is not all that uncommon. After several months and many hearings my lawyer managed to convince me of this, and urged me to plea as I would have a drastically less severe sentence. I got (and served) a few years. But the whole episode was incredibly revealing as to how fucked and illogical the entire legal system is.

 

[Hammilton]

If you plead out you weren't convicted, you admitted guilt. If you had gone to court you probably could have won on that one charge, but lost all the others for things you actually did do. Did the math work out in your favor? Probably.

Had you only been charged with the 2C-B manufacture you would have been well served to fight it. Even if you had been convicted, you would have had good grounds to appeal, but it gets expensive quick.

When liberty is on the line, though, money doesn't seem like such a major issue (if you're able to obtain it). If you're not able to obtain it, you're fucked.

 

[amanitadine]

`^^^^ Granted. And yes, the math worked out in my favor, in a most dramatic way ( by a factor of about 5) as did the amount of money I had to spend. While we were going through the various hearings and waiting for forensics results, my attorneys found several cases in which the juries returned guilty verdicts on charges for substances that were not even produced, a few way more dramatic than mine. You are correct, it does make a good case for an appeal, and in theory you might eventually find a jury with enough of a collective brain to acquit, but it was amazing to me how idiotic it all was. I believe the huge influx of meth manufacturing cases and all around meth hysteria has made it alot harder to get a case fairly tried in the United States. If you have an endless supply of money, you might get off eventually. I fought my various charges for about a year, (most of that time was spent waiting on forensics, so my lawyer bills were quite small for such a long period of time) and I still spent 50k, and I didnt even get to trial.

I won't go into details , as this isn't the place for it, and some of it is compromising as to my identity, but after getting busted (and being an active member of the psychedelic community and online community for the pst 15 yrs) it was astounding to go over my case, and those of many others who i either knew online or met after getting busted. In none of these cases was detective work the primary cause, and in all but one the internet played absolutely no role. The paranoia amongst those who haven't been busted I find hilarious.

Cheers

 

[skillet]

Well I guess stories like this are the cause of the paranoia! That sounds horrible. Out of curiosity, why didn't you just make 2C-B? It's easier and more potent.

 

[amanitadine]

It was horrible but not nearly as horrible as you make it out to be for the years preceding getting busted. This seems to be a universal observation.

And, 2C-B was old hat by then. and there were organizations that could do it better and cheaper than I. 2C-C was still a relatively novelty, and as the markets for these sort of things were growing exponentially it was an item I could provide competitively. This is all irrelevant now, as the "research chemical" market put scores of dudes like me outta business. Can't compete with China!

yet another victim of Globalization

 

[skillet]

I'm not sure what you mean. It was worth it overall? It was only horrible after getting busted? I'm not sure how I made it out to be, but a year of legal bullshit, 50k dollars(?) and a few years in jail sounds pretty bad to me.

 

[23536]

...my attorneys found several cases in which the juries returned guilty verdicts on charges for substances that were not even produced, a few way more dramatic than mine. You are correct, it does make a good case for an appeal, and in theory you might eventually find a jury with enough of a collective brain to acquit.

One of the things that most shocked me about the US when I got here was that juries can come to any decision they want, laws be damned. I imagine that once a defendant starts using even very basic chemistry to bolster his defense, he just starts looking creepier to a jury of his supposed peers.

 

[amanitadine]

^^^ That hits the nail on the head right there. It is shocking and has left me with a "soured" view of our legal system, among other things

Skillet - Let me rephrase: As you spend years of worrying about getting busted the stress just builds and builds...and when the deed finally happened it was rather anit-climactic. Almost a relief even. Sure, it was awful. . I lost everything, was under immense stress for a long period, and then did a few years in prison. But it wasn't as bad as I had feared. For several years I faced a certainty that should the worst happen I would be strung up for many many years. But it was just a handful of years, and prison was more boring than anything else. Honestly it has been more challenging since being released and having all of this inapplicable knowledge and experience, trying to find a new direction in life, and operating as someone with multiple felonies and a persistent bad taste in the mouth. But I earnestly have few regrets...at this point it still feels worth it most days.

Cheers

ps - and yes, about 50k dollars. roughly half of this was attorneys fees, the other portion fines and such. And my plea let me off the hook for over 100k in fines for environmental fines, forensics and such,, and "clean up" costs for my lab. Which was a spic and span place that received no "clean up" save for confiscation and forensics sampling. The forensic reports were almost worth the exorbitant costs alone (would I have paid them in currency rather than time), as they meticulously analyzed a shit ton of products, intermediates, and waste. That part was fascinating as I was lacking higher tech analytical equipment and rarely had access.