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What is wrong with the MDMA available today? - v2

unodelacosa

Bluelighter
Joined
Feb 23, 2021
Messages
101
@Gaffy – you're talking about the sodium cyanoborohydride reduction from MDP-2-P and the use of Palladium II Chloride as a metal catalyst in some form of oxidation. The p-benzoquinone Wacker oxidation really limits the amount of necessary (and expensive) Pd2Cl, but I think Shulgin took the performic acid route from isosafrole, no? And anyway, Al/Hg amalgam with methylamine either separately obtained or created in situ is an elegant reaction suffering only from having to work with deadly poisonous Mercuric chloride salts.

@indigoaura – ok first off, where are the references in this Wikipedia article? Lots of statements made, no sources given for them. "[MDMA] synthesized by methylation of MDA using methylating reagents such as methyl iodide" … this, to me, does not seem like it would happen too often as a realistic approach to manufacturing MDMA, not when so many other options exist for producing a methylated amine. Sure, it would reveal the method used, I suppose, and it does seem like excess reagent + excess heat would lead to this dimethylated formation, but I'd have to see evidence and actual numbers before I would believe this happens any kind of frequently.

Secondly there isn't exactly a wealth of information out there vis-à-vis the subjective effects of MDDM and how they combine with MDMA's effects. It's an interesting theory to consider, but it's far from conclusive.
 

indigoaura

Bluelighter
Joined
Jan 4, 2009
Messages
1,569
@Gaffy – you're talking about the sodium cyanoborohydride reduction from MDP-2-P and the use of Palladium II Chloride as a metal catalyst in some form of oxidation. The p-benzoquinone Wacker oxidation really limits the amount of necessary (and expensive) Pd2Cl, but I think Shulgin took the performic acid route from isosafrole, no? And anyway, Al/Hg amalgam with methylamine either separately obtained or created in situ is an elegant reaction suffering only from having to work with deadly poisonous Mercuric chloride salts.


@indigoaura – ok first off, where are the references in this Wikipedia article? Lots of statements made, no sources given for them. "[MDMA] synthesized by methylation of MDA using methylating reagents such as methyl iodide" … this, to me, does not seem like it would happen too often as a realistic approach to manufacturing MDMA, not when so many other options exist for producing a methylated amine. Sure, it would reveal the method used, I suppose, and it does seem like excess reagent + excess heat would lead to this dimethylated formation, but I'd have to see evidence and actual numbers before I would believe this happens any kind of frequently.

Secondly there isn't exactly a wealth of information out there vis-à-vis the subjective effects of MDDM and how they combine with MDMA's effects. It's an interesting theory to consider, but it's far from conclusive.

I 100% agree that Wikipedia is not a reliable source and could not be cited academically. I meant it to be a quick reference point.

The PIKHAL report is one reliable account of effects, and I shared that link as well. I also shared an academic article about an overdose where MDDM was found in tissue.

Would you have time to do some research and find some other articles on MDDM/MDDA and share them here? I will be looking as well.

"Secondly there isn't exactly a wealth of information out there vis-à-vis the subjective effects of MDDM and how they combine with MDMA's effects. It's an interesting theory to consider, but it's far from conclusive."

I would not consider it conclusive either. However, we do have one sample of subpar product that contains this contaminant, and another with a contaminant identified as MBDB. I will be sending that same sample off to IEC to see if they identify MBDB, or if perhaps the MBDB was mid-identified. I also would not necessarily expect there to be a wealth of information about the subjective effects of mixing a new psychoactive compound with MDMA, especially when the new psychoactive compound has less than stellar effects noted in PIKHAL. There are not a lot of studies being done about subjective effects of new/unfamiliar compounds in combination with other illegal compounds.

I also want to point out that this sample was previously tested, and the result was - MDMA. Specifically, 80% MDMA. It took HPLC and a lot of additional effort for her to identify that a contaminant was also present. The article I posted also commented on how difficult it was for MDDM to be identified in lab results for MDMA. So, for all the lurkers/readers who have commented that the initial test results should be taken at face value, that is simply not the case. More advanced testing provides more detailed results. This is supported repeatedly through published research.

My next steps are to send IEC my other meh samples to see if they contain the same contaminant.

If anyone knows how MDMA could be successfully separated from MDDM, let me know.
 

indigoaura

Bluelighter
Joined
Jan 4, 2009
Messages
1,569
The link to open this on Sci Hub is not working for me, but it seems to be particularly relevant research.

Binding Mode Selection Determines the Action of Ecstasy Homologs at Monoamine Transporters - PubMed

Determining the structural elements that define substrates and inhibitors at the monoamine transporters is critical to elucidating the mechanisms underlying these disparate functions. In this study, we addressed this question directly by generating a series of N-substituted...
pubmed.ncbi.nlm.nih.gov
pubmed.ncbi.nlm.nih.gov

Starting with 3,4-methylenedioxy-N-methylamphetamine, 3,4-methylenedioxy-N,N-dimethylamphetamine (MDDMA) and 3,4-methylenedioxy-N,N,N-trimethylamphetamine (MDTMA) were prepared. We evaluated the functional activities of the compounds at all three monoamine transporters in native brain tissue and cells expressing the transporters.
Note that in this article they are referring to 3,4-methylenedioxy-N,N-dimethylamphetamine as MDDMA.

Our results suggest that the 3,4-methylenedioxyamphetamine analogs bind at the monoamine transporter orthosteric binding site by adopting one of two mutually exclusive binding modes. 3,4-methylenedioxyamphetamine and 3,4-methylenedioxy-N-methylamphetamine adopt a high-affinity binding mode consistent with a transportable substrate, whereas MDDMA and MDTMA adopt a low-affinity binding mode consistent with an inhibitor, in which the ligand orientation is inverted. Importantly, MDDMA can alternate between both binding modes, whereas MDTMA exclusively binds to the low-affinity mode.

Pifl already established that some impurities can bind to transporters and block the effects of MDMA. So, here in this article, they seem to be stating that MDDMA has the same inhibitory impact at the monoamine transporters.
 

indigoaura

Bluelighter
Joined
Jan 4, 2009
Messages
1,569
@unodelacosa

I found this:
Therefore, it can be assumed that MDDM was present as a synthesis by-product or impurity in the “ecstasy” tablets taken by the victim. Gimeno et al. substantiated that MDDM can be formed during the clandestine manufacture of MDMA by reductive amination of 3,4-methylenedioxyphenyl-2-propanone (MDP2P) by dimethylamine [20, 21]. This MDDM formation takes place because of the presence of dimethylamine as a contaminant in methylamine [22].

Link: https://sci-hub.st/10.1007/s00414-006-0094-x
Title: Postmortem distribution of 3,4-methylenedioxy-N, N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose
Author: De Letter, E. A.
 

indigoaura

Bluelighter
Joined
Jan 4, 2009
Messages
1,569
We were talking about MDDMA in the original thread in relation to the NMR results shared by Vash. I know that situation got weird, but assuming those NMR results were valid, remember how we were trying to figure out what the additional peaks were? We compared the peaks to published data and were speculating that it looked a lot like MDDMA. Check the posts from around #3661, or just do a search for MDDMA and they will all appear.
 

unodelacosa

Bluelighter
Joined
Feb 23, 2021
Messages
101
We were talking about MDDMA in the original thread in relation to the NMR results shared by Vash. I know that situation got weird, but assuming those NMR results were valid, remember how we were trying to figure out what the additional peaks were? We compared the peaks to published data and were speculating that it looked a lot like MDDMA. Check the posts from around #3661, or just do a search for MDDMA and they will all appear.
I've been thinking this subject over a bit before responding and thinking about the synthesis, especially from the perspective of a clandestine chemist acquiring a bulk shipment of PMK-glycidate, and what that would entail in terms of processing that quantity.

Some 20-odd years ago I used to synthesize compounds including MDMA. Obtaining methylamine, even back then, would quickly draw the unwanted attention of law enforcement, and so unless one could devise a way to steal or divert the reagent-grade methylamine, one would have to "side-synth" their own batches of methylamine to use in reductive amination. Without going into detail, I would circumvent this impracticality through a clever _in situ_ synthesis involving an OTC high-octane racing fuel. Scaling this process up industrially would've likely brought out some of the, shall we say, demerits of this method and potential hazards as well. Meaning to say, it's likely an underground chemist would manufacture their own methylamine, and the synthesis most likely involved would co-currently synthesize methylamine, dimethylamine, and I think trimethylamine. Idk, it's discussed briefly in its wikipedia article if memory serves. Anyway, if these -amines are not properly separated–as one might expect could happen in untrained hands operating a clandestine lab–then it's totally plausible that dimethylamine impurity could be substantial enough to affect cosynthesis of the side-product MDDM, sure.

But there are numerous possibilities for accidental co-synthesis of active impurities associated with different synthetic routes. For example, in another thread I was mentioning how clandestine chemists have been known to use too much heat when refluxing safrole in the production of isosafrole. The result is a breaking open of the 3,4-methylenedioxy ring which forms a new compound: a 3,4-dihydroxy-benzene, this making it a catechol as well. If this impurity follows along the same synthesis as whatever safrole manages to convert to isosafrole unharmed, then the end product could easily also have 3,4-dihydroxymethamphetamine, for example, which has strong stimulant properties and a less pronounced empathogenic effect compared to 3,4-MDMA. In the past, this has been theorized to be one of the causes in different subjective data, anecdotal reports, and qualitative musings regarding the variance in perceived effects from consumption of illicit “MDMA”, “ecstasy”, and/or “molly”.

There is info out there about 3,4-dihydroxymethamphetamine, as it's also a metabolite of MDMA… https://www.erowid.org/references/refs_view.php?ID=682

EDIT: And I mean to add, points well made, @indigoaura – you lay out a fairly well reasoned argument. It's something best validated with substantial evidence and the nature of the illicit market does not easily oblige this, as it were.
 

unodelacosa

Bluelighter
Joined
Feb 23, 2021
Messages
101
If anyone knows how MDMA could be successfully separated from MDDM, let me know.
Well my first thought was perhaps a very careful, arduous, fractional vacuum distillation. But it's likely the boiling points might still be too close. Let's see, I'm cracking open my copy of The Shulgin Index to look up the entry on MDDM (or as it's listed in the book, MDDMA).

MDDMA freebase's boiling point is listed as "85-88 °C/0.15 mm (Braun et al., 1980)".
Meanwhile MDMA freebase boils at "100-110 °C/0.4 mm."

Maybe don't totally rule that one out. However, in the same reference manual under the entry for MDDMA, it notes:

Structural homologues were separated by liquid chromatography (Noggle et al., 1987a) and LC/CS (Noggle et al. 1988)

I'm thinking a proper chromatography column is what you would need. Not "high performance" or "GC-MS", just simple separation…
 

indigoaura

Bluelighter
Joined
Jan 4, 2009
Messages
1,569
Well my first thought was perhaps a very careful, arduous, fractional vacuum distillation. But it's likely the boiling points might still be too close. Let's see, I'm cracking open my copy of The Shulgin Index to look up the entry on MDDM (or as it's listed in the book, MDDMA).

MDDMA freebase's boiling point is listed as "85-88 °C/0.15 mm (Braun et al., 1980)".
Meanwhile MDMA freebase boils at "100-110 °C/0.4 mm."

Maybe don't totally rule that one out. However, in the same reference manual under the entry for MDDMA, it notes:



I'm thinking a proper chromatography column is what you would need. Not "high performance" or "GC-MS", just simple separation…

Thank you for your replies.

"I'm thinking a proper chromatography column is what you would need. Not "high performance" or "GC-MS", just simple separation…"

Everything seems to keep coming back to this. Column chromatography is part of the MAPS process of purification, and other users have speculated this is what is needed to truly get good results.

I have gone back and forth about buying what is needed to complete the chromatography myself. However, there seems to be a lack of clarity regarding which solvent would work best. Until I have an accurate idea of which solvent to use, I am hesitant to proceed with a costly operation. If I knew for certain that it would work, then I would make the investment. Do you have any suggestions regarding which solvent to use in a column?

"But there are numerous possibilities for accidental co-synthesis of active impurities associated with different synthetic routes. "

Yes. I have seen this in many research articles, and even MAPS references the phenomenon when providing an overview of their synthesis process. They discuss that ambient temperature can impact the result in significant ways.

Update from International Energy Control.

They were unable to quantify the 3,4-methylendioxy-N,N dimethylamphetamine because they do not have the standard for it. I asked if it would be possible to donate the standard so quantification of this impurity would be possible. They are looking into that now, and they are going to let me know what the cost would be.

My plan going forward is as follows:
-Donate the standard for 3,4-methylendioxy-N,N dimethylamphetamine to IEC
-Submit additional meh samples

If my hypothesis is correct, then I would expect to see the same/similar impurity in other samples. I hope that if multiple samples with subpar effects contain the same impurity then perhaps I may be more able to gain the attention of a researcher or university.
 

RyybsNarcs

Greenlighter
Joined
Sep 30, 2019
Messages
12
Thank you for your replies.

"I'm thinking a proper chromatography column is what you would need. Not "high performance" or "GC-MS", just simple separation…"

Everything seems to keep coming back to this. Column chromatography is part of the MAPS process of purification, and other users have speculated this is what is needed to truly get good results.

I have gone back and forth about buying what is needed to complete the chromatography myself. However, there seems to be a lack of clarity regarding which solvent would work best. Until I have an accurate idea of which solvent to use, I am hesitant to proceed with a costly operation. If I knew for certain that it would work, then I would make the investment. Do you have any suggestions regarding which solvent to use in a column?

"But there are numerous possibilities for accidental co-synthesis of active impurities associated with different synthetic routes. "

Yes. I have seen this in many research articles, and even MAPS references the phenomenon when providing an overview of their synthesis process. They discuss that ambient temperature can impact the result in significant ways.

Update from International Energy Control.

They were unable to quantify the 3,4-methylendioxy-N,N dimethylamphetamine because they do not have the standard for it. I asked if it would be possible to donate the standard so quantification of this impurity would be possible. They are looking into that now, and they are going to let me know what the cost would be.

My plan going forward is as follows:
-Donate the standard for 3,4-methylendioxy-N,N dimethylamphetamine to IEC
-Submit additional meh samples

If my hypothesis is correct, then I would expect to see the same/similar impurity in other samples. I hope that if multiple samples with subpar effects contain the same impurity then perhaps I may be more able to gain the attention of a researcher or university.
I've seen reports that used Methanol/DCM mixture as a solvent for column chromatography, ratio was 90% DCM and 10% Methanol. Also recommended to perform an acetone wash to your MDMA sample before purifying it with column.
 

Zuda

Bluelighter
Joined
Feb 21, 2017
Messages
101
Location
Tennessee
Good, so it's not just me. Literally all of the MDMA I've come across recently has been pure garbage. As a quick field-test for MDMA you're supposed to throw a small sample on aluminum foil, and then heat up a small flame under it. If it melts into an opaque, blood-red puddle, it's MDMA (the oxygen molecules produce the red color. So far no other chemical has produced the same result.) I had MDMA recently that melted into a semi-translucent, yellow puddle when tested in this manner. Literally all of it has made me feel like I'm dying. I miss the good ole brown shit with the white dust on it. As it stands now, I'm scared to try anything that's going around. Stuff just makes me feel like I'm dying. I'm guessing the problem is meth
 

Zuda

Bluelighter
Joined
Feb 21, 2017
Messages
101
Location
Tennessee
If the issue is getting sold meth, your problem could be easily solved by replacing your lighter with a $20 vial of the Marquis reagent.
I have one of those, and the lighter test is far easier to read. The main problem was that I melted some down, it turned out to not be what I had paid for, and I did it anyway. ONLY pure MDMA melts into a blood-red puddle. Meth melts clear. A combination of the 2 could certainly have produced a semi-translucent yellow. But anyway, I'm not going to be seeking or purchasing any "MDMA" for a long time.
 
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