2,3 MDMA or 6-Methy MDA - low potency Positional/Functional Isomers of MDMA

[Jabberwocky]

Both have low potency and could potentially be identified as MDMA by GCMS

 

[aced126]

That is not how synthesis works. No clandestine chemist would set out to make these positional isomers on purpose.

 

[Jabberwocky]

That is not how synthesis works. No clandestine chemist would set out to make these positional isomers on purpose.

Exactly, nobody would set out to make the r-isomer of MDMA on purpose either.

But regardless of what someone would likely do, the fact remains in the absence of Ion Mobility or UV/IR VIS, positional isomers will be identified as MDMA by GCMS. Structural isomers will as well, depending on when they elute from the column.

 

[Black]

By far the most common and perhaps standard form of ionization is electron ionization (EI). The molecules enter into the MS (the source is a quadrupole or the ion trap itself in an ion trap MS) where they are bombarded with free electrons emitted from a filament, not unlike the filament one would find in a standard light bulb. The electrons bombard the molecules, causing the molecule to fragment in a characteristic and reproducible way.

you easily see those isomers with ei, which is not specialised but rather the most standard method for creating ions for gc/ms.

 

[aced126]

Yes, of course these positional isomers will be identified as MDMA in a GCMS. It is also possible to be struck by lightning. Both these events have extremely low probabilities of occuring (no practical MDMA sample will contain its positional isomers, unless the chemist adds it in on purpose, which makes no sense).

Also, gas chromatography should be able to separate the 2 compounds and they should appear as different peaks. If both the peaks have the same molecular ion peak then the compounds can then either be identified by fragmentation patterns or NMR spectroscopy.

 

[Jabberwocky]

Yes, of course these positional isomers will be identified as MDMA in a GCMS. It is also possible to be struck by lightning. Both these events have extremely low probabilities of occuring (no practical MDMA sample will contain its positional isomers, unless the chemist adds it in on purpose, which makes no sense).

Also, gas chromatography should be able to separate the 2 compounds and they should appear as different peaks. If both the peaks have the same molecular ion peak then the compounds can then either be identified by fragmentation patterns or NMR spectroscopy.

I'm proposing a possible reason for GC/MS tested MDMA to actually not be 3,4 MDMA

ION Mobility can identify suspected positional or structural isomers, SIM can't it's only looking for 1 mass

-- NMR I'm pretty sure is not being done for $40/test

 

[Jabberwocky]

you easily see those isomers with ei, which is not specialised but rather the most standard method for creating ions for gc/ms.

Really? the ions from 2,3 MDMA and 3,4 MDMA would be identical -- same with 5/6 Methyl MDA

C11H15NO2

Now maybe if it was electrospray, so the fragmentation wasn't so intense, you could differentiate the functional groups

 

[aced126]

I'm proposing a possible reason for GC/MS tested MDMA to actually not be 3,4 MDMA

ION Mobility can identify suspected positional or structural isomers, SIM can't it's only looking for 1 mass

-- NMR I'm pretty sure is not being done for $40/test

Your proposed reason is not a sensible nor likely reason that GCMS tested MDMA is not MDMA, because no chemist would do that on purpose. It's like proposing that most scientific papers are plain lies. This is not the case, as in most scientific papers there is no conflict of interest.

 

[Jabberwocky]

Your proposed reason is not a sensible nor likely reason that GCMS tested MDMA is not MDMA, because no chemist would do that on purpose. It's like proposing that most scientific papers are plain lies. This is not the case, as in most scientific papers there is no conflict of interest.

It's more likely a research chemical that is a positional or structural isomer is misclassified as MDMA by GCMS (happens all the time) --

than it is someone:

purposely synthesized r-MDMA (cause its a lot harder to do) or

separated the isomers of racemic MDMA (cause that's expensive and can only be done with chiral acids -- so if you want the HCl salt (which it supposedly is) -- you would have to use a chirally specific acid, create the salt (probably tartrate as it can be chiral and can be bought as a specific chiral) -- then re-extract the freebase and re-precipitate with HCL

or someone unintentionally stumbled upon a synthesis that didn't make goo, didn't explode, and managed to make isomerically pure r-MDMA

 

[Yeetbeat]

Ummm

CSB?

 

[Jabberwocky]

Ummm

CSB?

UMM -- if you don't really give a fuck

why be a douche and call the story Cool?

 

[Black]

Really? the ions from 2,3 MDMA and 3,4 MDMA would be identical -- same with 5/6 Methyl MDA

C11H15NO2

Now maybe if it was electrospray, so the fragmentation wasn't so intense, you could differentiate the functional groups

pma and ephedrine are both C10H15NO. see the other thread.

what's the last sentence supposed to mean? you confuse me.
you can differentiate functional groups especially good when you get lots of fragmentation. also if you have lots of fragmentation you often don't see the molecule ion at all. so you'd get different patterns for those compounds anyway.

 

[redshark]

j
j
j

 

[Jabberwocky]

pma and ephedrine are both C10H15NO. see the other thread.

what's the last sentence supposed to mean? you confuse me.
you can differentiate functional groups especially good when you get lots of fragmentation. also if you have lots of fragmentation you often don't see the molecule ion at all. so you'd get different patterns for those compounds anyway.

Yeah and PMA and ephedrine are NOT positional or structural isomers of MDMA -- they don't even have the same mass.

The point is the functional groups are the same -- and the type and number of ions are the same, unless you look at ION Mobility or NMR (NMR is just not done) --

 

[Black]

Yeah and PMA and ephedrine are NOT positional or structural isomers of MDMA -- they don't even have the same mass.

The point is the functional groups are the same -- and the type and number of ions are the same, unless you look at ION Mobility or NMR (NMR is just not done) --

but they're positional isomers of each other. ephedrine vs. pma is like mdma vs. 5/6-methyl-mda. neither pair has identical functional groups.

but even with 2,3-mdma you have different fragments after ei. you can look at them with every kind of ms detector (sector field, tof, quadrupol, ...) . i don't know why you fixate so much on ion mobility — as far as i understand (it's not a very usual method and certainly not one i know a lot about) its only real advantage is higher sensitivity, which is rather needed to detect trace amounts for forensics rather than detecting normal amounts in a pill. with a simple ms (using ei and sector field) you get quite different spectrums for 2,3 and 3,4. no need for specialised methods.

 

[aced126]

It's more likely a research chemical that is a positional or structural isomer is misclassified as MDMA by GCMS (happens all the time) --

than it is someone:

purposely synthesized r-MDMA (cause its a lot harder to do) or

separated the isomers of racemic MDMA (cause that's expensive and can only be done with chiral acids -- so if you want the HCl salt (which it supposedly is) -- you would have to use a chirally specific acid, create the salt (probably tartrate as it can be chiral and can be bought as a specific chiral) -- then re-extract the freebase and re-precipitate with HCL

or someone unintentionally stumbled upon a synthesis that didn't make goo, didn't explode, and managed to make isomerically pure r-MDMA

Any examples of research chemicals satisfying these conditions? I cannot think of any.

 

[Jabberwocky]

Any examples of research chemicals satisfying these conditions? I cannot think of any.

The mass spectra of the controlled substance 3,4-MDMA and its regioisomer 2,3-MDMA are characterized by an imine fragment base peak at m/z 58 and additional fragments at m/z 135/136 for the methylenedioxybenzyl cation and radical cation, respectively. Three positional ring methoxy isomers of N-methyl-2-(methoxyphenyl)-3-butanamine (MPBA) have an isobaric relationship to 2,3- and 3,4-MDMA. All five compounds have the same molecular weight and produce similar EI mass spectra.

This lack of mass spectral specificity for the isomers in addition to the possibility of chromatographic co-elution could result in misidentification. The lack of reference materials for the potential imposter molecules constitutes a significant analytical challenge.

http://www.ncbi.nlm.nih.gov/pubmed/21549024

Wait a minute -- some guy was posting exactly the same thing .....

Oh and here is a paper that identifies

LC–ESI-MS–MS is necessary to differentiate

https://chromsci.oxfordjournals.org/content/43/2/92.full.pdf


and next is a paper that shows even HPLC can have issues

Several organic solvents were examined for the mobile phase, and the results were plotted and analyzed. The most advantageous conditions for 3,4-MDMA turned out to be a gradient acetonitrile/buffer system. Again, however, 2,3-MDPE came off the column very closely to 3,4-MDMA. http://pubs.acs.org/subscribe/archive/tcaw/10/i02/html/02inst.html

 

[Biscuit]

2,3 MDMA or 6-Methy MDA - low potency Positional/Functional Isomers of MDMA - Both have low potency and could potentially be identified as MDMA by GCMS

The forensic government laboratories cannot afford to misidentify seized drugs in drug prosecutions; if this routinely occurred, it would bring the entire system into disrepute. The mass spectra of the chemicals you have mentioned would not be the same as the mass spectra for MDMA. If these chemicals were present in pills, then the laboratory would need to identify them precisely or, if they had no reference data for such novel compounds and couldn't identify them, then the substance would be reported as not containing ANY identifiable illicit or prohibited drug. They cannot just pretend it is MDMA, even though no one else is going to know any different.

What you have stated also ignores the recent data that we have from various government agencies, such as the United Nations, Australian Crime Commission and the European Drug investigation agency (the name escapes me). The reports put out by these agencies have all identified PMK-glycidate as the most common MDXX precursor seized worldwide. What we would have to agree on is the MDMA analogues that you mentioned above are NOT being manufactured from PMK-glycidate. The very issue being debated is a common phenomenon reported by ecstasy users worldwide. It is no coincidence that the most prevalent MDMA precursor over the past several years also appears to be the source of the most prevalent problem/issue/complaint made by ecstasy users over the past several years.

 

[Yeetbeat]

Well I wouldn't put it past them at least trying to pretend it's MDMA

 

[Yeetbeat]

On topic: Biscuit - did you mean to suggest that the issues MDMA is presenting these issues as a result of by-product contamination in PMK-glycidate synth'd MDMA? As in - the by-products created during imperfect clandestine synthesis of MDMA when using PMK-glycidate as the precursor are potentially responsible for the prevalence of negative effects reported by MDMA users these past years?