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Trimethoxymethamphetamine

blowjay

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Another thought as I am trying to go to sleep, thinking of the alephs and then I realize that I have never heard of trimethoxymethamphetamine. Everyone hears of mescaline and then some hear about TMA but this has never been brought to my attention until now. Now why exactly did shulgin decide to stop at TMA when he could have ventured into this? Makes since to me as he loved MDMA so much and mescaline is what started him on this whole thing, how in the fuck do you overlook something so obvious as this? Is there a problem in synthesizing this or what would be the drawback?

I have heard MDMA being described as a chemical combination of mescaline and meth in propaganda but this is the real thing. Someone help me out here as this sounds to me like it could be a lost gem.
 

atrollappears

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You obviously have not read PiKHAL. ;)
From the chapter "TMA":
"I was handed a rose (which under mescaline would have been precious and entrancing) and was asked if I could hurt it. I crushed it without hesitation. At that point, Terry asked me if I might consider taking a small amount of a tranquilizing medication. My response was a thinly veiled threat to push him downstairs if he tried to medicate me. He didn't push the subject."
The potency is around that of mescaline, and the subjective effects are by all accounts of a purely psychedelic nature but just not that fun.
 

Psyke

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I think the OP was saying, why did He stop at TMA instead of venturing into TMMA. Plain old TMA would be tri-methylamphetamine instead of tri-methlymethamphetamine. Correct me if i'm wrong OP
 

atrollappears

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I think the OP was saying, why did He stop at TMA instead of venturing into TMMA. Plain old TMA would be tri-methylamphetamine instead of tri-methlymethamphetamine. Correct me if i'm wrong OP

Oh of course. Well such a compound would probably be inactive, I think even the n-methylated DOx are inactive. I'm puzzled, really, why MDMA is psychedelically active, if it is, beyond being demethylated into the agonist MDA (endogenous serotonin doesn't really evoke psychedelia because it doesn't activate the right signal transduction pathway through the 5-HT2A receptor) And as far as being an entactogen like MDMA, those methoxy groups just don't seem to sit well with SERT. Even MMDA, which differs from MDA by only one methoxy group, is purely psychedelic, not entactogenic beyond what a normal psychedelic is.
 

dip12

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Three additional N-methylated homologues of known psychedelics warrant mention, but do not really deserve separate recipes. This is because they have had only the most cursory assaying, which I have learned about by personal correspondence. All three were synthesized by the reduction of the formamide of the parent primary amine with LAH. METHYL-TMA (or N-methyl-3,4,5-trimethoxyamphetamine) had been run up in several trials to a maximum of 240 milligrams, with some mental disturbances mentioned only at this highest level. METHYL-TMA-2 (or N-methyl-2,4,5-trimethoxyamphetamine) had been tried at up to 120 milligrams without any effects. METHYL-TMA-6 (or N-methyl-2,4,6- trimethoxyamphetamine) had been tried at up to 30 milligrams and it, too, was apparently without effects. These are reports that I have heard from others, but I have had no personal experience with them. Those that I can describe from personal experience are entered separately as recipes of their own. And there are many, many other N-methyl homologues which have been prepared and characterized in the literature, and have yet to be tasted. So far, however, the only consistent thing seen is that, with N-methylation, the potency of the psychedelics is decreased, but the potency of the stimulants appears to be pretty much maintained.
(taken from METHYL-DMA entry: http://www.erowid.org/library/books_online/pihkal/pihkal126.shtml)
 

atrollappears

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Good find, dip12!

NBOME-TMA might be interesting I guess

Maybe, but as far as the SAR holds true (though often SARs don't), it would probably not be active. I say this because DOx compounds are actually much *more* potent than their NBOME analogs, so if this holds true for the 3 rather than 4 substituted amphetamine TMA, the potency of the compound would decrease to a practically inactive level.
 

dip12

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Hazard a guess that the subjective effects of N-methyl-TMA dosed up to 240mg might be from TMA which could likely be an active metabolite. I.e N-methy-TMA itself might be truely inactice. The effects resulting from the slow and incomplete metabolism to TMA.
 

blowjay

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Hazard a guess that the subjective effects of N-methyl-TMA dosed up to 240mg might be from TMA which could likely be an active metabolite. I.e N-methy-TMA itself might be truely inactice. The effects resulting from the slow and incomplete metabolism to TMA.

I don't see the basis for that guess and just keep wanting to point towards MDMA and MDA. I would guess that the levels have not been hit for the TMMA activity to show itself. It seems very weird that it would go from an increase to a decrease in potency as MDA to MDMA is an increase in potency and MDPEA is inactive. Here we go from Mescaline; active but not potent, to TMA; active and an increase in potency, to TMMA which is said to be less potent than TMA. Certainly not what I would expect but this is second hand data from shulgin and there could be more we don't know.

I do believe though that he (or wikipedia can't remember) says the N-methyl version of 2c-b has a decrease in potency so I can see it applying in this case, still confusing as hell due to MDMA being the way it is. I may just be wanting this thing to have more potential than it does but I think it would be silly to write it off as uninteresting.
 

poopstation

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TMMA-2, DMMDMA, MMDMA, all are only slightly active at massive doses in relation to their primary amine per trials by antibody2 and chromic at the hive.

PMMA is another one that breaks the rules, of course it's toxic garbage but it's absolutely active in its own right just as MDMA is.
 

Vader

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N-methyl on a phen kills 5HT2a agonism entirely IIRC. Shulgin says the only phen that yielded anything interesting with a methyl on the amine was MDMA, which is hardly typical given that MDA is a monoamine releaser as well as an agonist.
 

atrollappears

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It seems very weird that it would go from an increase to a decrease in potency as MDA to MDMA is an increase in potency and MDPEA is inactive. Here we go from Mescaline; active but not potent, to TMA; active and an increase in potency, to TMMA which is said to be less potent than TMA. Certainly not what I would expect but this is second hand data from shulgin and there could be more we don't know.

You're talking about totally different methods of action. MD(M)A are serotonin releasers, whereas TMA (and possibly TMMA) is an agonist. You can't apply the same SAR to different mechanisms. But still, very Shulgin-esque of you (he once tried to turn THC into a phenethylamine to try to increase or improve its activity =D) and I admire your curiosity on the subject. :D
 

blowjay

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TMMA-2, DMMDMA, MMDMA, all are only slightly active at massive doses in relation to their primary amine per trials by antibody2 and chromic at the hive.

PMMA is another one that breaks the rules, of course it's toxic garbage but it's absolutely active in its own right just as MDMA is.

That is very interesting to hear, I can't quite grasp how MDMA is able to break the mold so much due to its extreme structural similarities to the compounds you mentioned, very weird is all I can say. I wonder what sulfur would do in place of the oxygens in MDMA or MDA?
 

blowjay

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I have found through google searches that TMMA has shown up in pressed pills in the past, very strange to see it get to that point but not even have a report of it being used, I wish there were at least 4 more shulgin's to make and test everything that looks interesting, the underground guys really need to follow his example and get on some of this stuff, I have too many ideas popping up and not enough time, knowledge, money, experience, and basically everything else to do this but it would be a dream (or nightmare at times I would guess).
 

atrollappears

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By the way, I should mention that the alpha- and n-methyl substitutions probably don't confer the action you're hoping for. PEA itself is active as a stimulant with high enough doses or coadministered with an MAOI; the alpha carbon only stops MAO from metabolizing the compound effectively, allowing it to easily reach the brain under normal circumstances. The same is true of the N-methyl group: it stops the compound from being broken down, and also increases lipophilicity and thus blood brain barrier permeability, but doesn't actually directly improve a compound's effectiveness. Regular amphetamine is actually more potent than meth once it's in the brain.
But whereas with releasing agents (amph/meth, MDMA or any other entactogen) n-methyl substitution leaves the compound's effectiveness intact, with serotonin agonists, i.e. psychedelics, n-methylation drastically reduces potency.

What is it that you hope to get out of this compound? A more psychedelic entactogen?
 

blowjay

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Most likely just a lower electronegativity.

Meaning higher dosage needed but a similarity to MDMA? This has also been one that has bugged me for a while too, can't see why he didn't jump on this as shulgin likes 2C-T's. I like just learning more about what these are being expected to be, very interesting to hear guesses towards activity.

And to atrollappears I am just wanting to know what it would do, I was hoping to hear it being a middleground between MDMA and Mescaline or a much more alert version of mescaline at worst.
 
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