Is SALT the cause of "MONGY" MDMA

[Jabberwocky]

Is THE SALT the cause of "MONGY" MDMA

Problem Statement:

There is GCMS Tested MDMA being produced that some people identify as providing non-representative dose-response -- ie "mongy".

Hypothesis for reported observation:

The "mongy" MDMA is not the HCl salt but some other salt (fumarate, (bi)tartrate, maleate, citrate, unknown). The combination of a (significantly) higher mass salt resulting in a lower amount of MDMA per dose, coupled with lower bioavailability, and different absorption kinetics, leads to the "mongy" effects, even though the MDMA is MDMA.

None of this has anything to do with precursor. It is the step where the freebase is reacted with an acid and precipitated to crystals.

Supporting Data:

1. HCl is a very light molecule, constituting approximately 16% of a dose of MDMA

2. Fumaric acid, citric acid, and tartaric acid are not light -- in fact citrate and tartrate weigh almost the same as MDMA mole wise -- if the compound formed = bitartrate, then 200mg would only contain about 75 mg of MDMA. (~35% )

3. The HCl salt is likely ~80% orally bioavailable based on excretion unchanged, and metabolites.

4. There is no data regarding the bioavailability of other MDMA salts. However, bioavailability of mineral supplements of maleate and citrate seem to be ~60%

5. MDMA HCl is absorbed through the stomach, reasonably quickly

6. We have no data on rate of absorption for these much larger molecules. However, citrate salts are absorbed to a significant degree in the intestine.


Thoughts??

 

[Black]

Thoughts??

common detection methods detect only the mdma itself (especially in gc you have freebase in the gas phase). so the dose given by the analytic methods doesn't depend on the salt at all.

lower bioavailability surprises me. mdma is a small, charged molecule (in salt form), so most salts should dissolve in water pretty fast.

 

[Jabberwocky]

common detection methods detect only the mdma itself (especially in gc you have freebase in the gas phase). so the dose given by the analytic methods doesn't depend on the salt at all.

lower bioavailability surprises me. mdma is a small, charged molecule (in salt form), so most salts should dissolve in water pretty fast.

RE: mg dose -- saferparty is the only source of MDMA mg on e-data their site identifies MDMA-HCl -- however, the explicit process is not identified -- it should be the freebase, however, I want to see the process describing how the lab actually extracts the MDMA salt and creates the freebase.

Citrate is a relatively large molecule compared to HCl, as are succinate, bitartrate, maleate -- and absorption profiles are unknown re: stomach vs intestinal

Lastly, I have not seen a trip report regarding the high dose pills In Zurich, Bern, Vienna that identifies the roll as weak -- in fact saferparty has a warning regarding dose for the high dose pills, these are the only pills that I have information on confirmed MDMA and mg content

 

[Kaden_Nite]

Salt variations are a possibility that hadn't crossed my mind.
Dextro or levo MDMA are another possibility.
Variations of positional isomers maybe?

Perhaps after 20-30 years of receptor-fucking MDMA making the rounds, followed by/including 5-10 years of 'research chemicals' being sold as MDMA, it's the people who are mongy?

 

[Jabberwocky]

Salt variations are a possibility that hadn't crossed my mind.
Dextro or levo MDMA are another possibility.
Variations of positional isomers maybe?

Perhaps after 20-30 years of receptor-fucking MDMA making the rounds, followed by/including 5-10 years of 'research chemicals' being sold as MDMA, it's the people who are mongy?

R-isomer is always bandied about, but it is more trouble to separate the isomers (you have to use a chiral acid), or start with r-MDA (another substance that requires one to want to make it using specialized synth).

I proposed a positional isomer like 2,3 MDMA (which without ion mobility GCMS you can't differentiate), but nobody bought it

I proposed structural isomers like 5/6 methyl-MDA which would show as MDMA by GCMS because of mass and functional groups, unless they had monographs in the database ( at least one online database identified as used for testing does not have them )


The truth of the matter is: any structural isomer (research chemical (RC)) of MDMA that elutes from the column at near the same time as MDMA (within the noise) will be identified as MDMA -- UNLESS there is data on that specific RC in the GCMS database used

UV/IR VIS could be used to differentiate, unless the spectral peaks are close

 

[Kaden_Nite]

I can't imagine salt variation playing much, if any, role in pharmacological effects, but depending on testing method, it may account for the large amounts of MD in some of the new-wave pressed batches (the ones shaped like spongebob and shit).

I know nothing about synth, but it would not surprise me if extremely creative and undocumented methodologies are currently being used which is why I would not rule out any variations in isomer (optical or structural).

Have you by chance tried any of these new 'Zurich/Vienna' batches and experienced this 'mongy' effect for yourself Shugenja? If so, can you summarise the difference?

 

[Black]

RE: mg dose -- saferparty is the only source of MDMA mg on e-data their site identifies MDMA-HCl -- however, the explicit process is not identified -- it should be the freebase, however, I want to see the process describing how the lab actually extracts the MDMA salt and creates the freebase.

they seperate when they're heated. it's impossible to get the salt into the gas phase. just liek with nacl if you heat it enough you get na vapour and cl2 vapour, but you'll never get nacl vapour. the process therefore is injecting your sample into port.
btw, the lab in vienna uses hplc; without ms in most cases when they're at parties. but here you also don't have the salt in solution but the seperate ions. you don't detect h+ and cl- when you're looking for organic molecules and an organic anion (like citrate or whatever) wouldn't come at the same retention time as mdma. you only detect the mdma itself.
with quantitative hplc it's usual to use an authentic standard, and i'm pretty sure they just correlate their "mdma" values to their weighted portion of mdma·hcl standard (skipping the chemical "·hcl" part to not confuse the druggies )

I proposed a positional isomer like 2,3 MDMA (which without ion mobility GCMS you can't differentiate), but nobody bought it

but wouldn't you have a different fragmentation pattern in the ms? (i haven't done ms in a long time, but iirc there should be a difference). same for 5/6-methyl-mda. and at least with the latter the peak in the chromatogram should also be different enough to attract attention.

edit:
turns out i'm right about ms. here is a paper available from maps about the topic. positional isomers don't produce the same fragmentation patterns.

Have you by chance tried any of these new 'Zurich/Vienna' batches and experienced this 'mongy' effect

i have a friend who has described the new batches as "very strong" and "almost like the first time". my contact with the party scene have become increasingly rare so i might not be the best informed, but i haven't yet heard anything about the new batches being inferior or different at all. the only thing i've heard is "finally there's an abundance of good mdma again".

 

[Jabberwocky]

but wouldn't you have a different fragmentation pattern in the ms? (i haven't done ms in a long time, but iirc there should be a difference). same for 5/6-methyl-mda. and at least with the latter the peak in the chromatogram should also be different enough to attract attention.

edit:
turns out i'm right about ms. here is a paper available from maps about the topic. positional isomers don't produce the same fragmentation patterns.

.

The paper identifies Electron Ionization and Collision Induced Dissociation, using Methane Chemical Ionization -- in other words Ion Mobility GCMS -- like I said

EI/CID is a specialized technique not normally used, unless positional or structural isomers are suspected.

That said, I was simply proposing what are IMHO more likely reasons for "Mongy " MDMA than some fantastical r-isomer synth -- and the extremely unlikely theory that somehow PMK-gly is used in some fantastical synthesis without converting it back to PMK (MDP2P) that makes crap MDMA.

I have never actually had a test confirmed MDXX that didn't provide the expected experience.

 

[Biscuit]

I have put my two cents worth in on this point, which you already raised in another thread:

http://www.bluelight.org/vb/threads/791073-What-is-wrong-with-the-MDMA-available-today/page12

 

[Black]

The paper identifies Electron Ionization and Collision Induced Dissociation, using Methane Chemical Ionization -- in other words Ion Mobility GCMS -- like I said

EI/CID is a specialized technique not normally used, unless positional or structural isomers are suspected.

That said, I was simply proposing what are IMHO more likely reasons for "Mongy " MDMA than some fantastical r-isomer synth -- and the extremely unlikely theory that somehow PMK-gly is used in some fantastical synthesis without converting it back to PMK (MDP2P) that makes crap MDMA.

I have never actually had a test confirmed MDXX that didn't provide the expected experience.

where in the world aren't ei or ci the standard for ms? for proteins or other biomolecules you might use maldi/tof, esi or something, but otherwise...
the only ms i've seen in person that didn't use ei or ci was a triple quad

and i agree about that. i'm not convinced that "mongy" new mdma actually exists. i've had experiences that fit the descriptions for new mdma ten years ago with batches that on other occasions produced spectacular results...

 

[Jabberwocky]

where in the world aren't ei or ci the standard for ms? for proteins or other biomolecules you might use maldi/tof, esi or something, but otherwise...
the only ms i've seen in person that didn't use ei or ci was a triple quad

and i agree about that. i'm not convinced that "mongy" new mdma actually exists. i've had experiences that fit the descriptions for new mdma ten years ago with batches that on other occasions produced spectacular results...

Ionization of course is done, but commonly SIM is used -- looking explicitly for 1 mass -- structural and positional isomers will match -- SCAN would see the same thing as the ions and child masses are identical (same functional groups)

Ion Mobility can differentiate isomers definitively, however -- normal EI just wont and when I said EI/CID -- I meant that both are not usually used in tandem -- only for unknowns.

For known or suspected substances, SIM is most likely the technique using EI after vaporization , or if the freebase, Electrospray

 

[Muzda Jonxx]

Perhaps after 20-30 years of receptor-fucking MDMA making the rounds, followed by/including 5-10 years of 'research chemicals' being sold as MDMA, it's the people who are mongy?

I agree with this. I won't touch MDMA anymore because there's simply no point. After 15 years of taking it, I had two choices. Take a normal dose (150-300mg) and get a bit mongy, or take a stupid dose (1g+), roll hard for a bit and then black out for 6 hours. For me, the party is over.

 

[Black]

Ionization of course is done, but commonly SIM is used -- looking explicitly for 1 mass -- structural and positional isomers will match -- SCAN would see the same thing as the ions and child masses are identical (same functional groups)

Ion Mobility can differentiate isomers definitively, however -- normal EI just wont and when I said EI/CID -- I meant that both are not usually used in tandem -- only for unknowns.

For known or suspected substances, SIM is most likely the technique using EI after vaporization , or if the freebase, Electrospray

sim is only useful when you're already sure what's inside and are only looking to quanify your substance. they'd never find mda or amphetamine or pma or whatever if they used sim for a random pill.

but wholly apart from that, if what you are saying were true, they also couldn't differentiate between the positional isomers ephedrine and pma (both being C10H15NO). and we know for sure that they can. if you cannot detect pma or would confuse it for ephedrine drug checking would be completely pointless.

 

[Kaden_Nite]

PMA's occasional appearance (still) is why I will never rule out the possibility of any substituted amphetamine appearing in pressed batches. Even if - especially if, it is an unlikely structural isomer of MDMA that may be able to be passed off as the real deal, if only for a while.

The fact that compounds such as DOC, AL-LAD & 2c-B-FLY are currently on the scene despite the complexity involved in their creation is why I believe that, chemically, new paths are being found all the time.

As for the current complaints about 'mongy' MDMA despite all chemical evidence telling us otherwise. I think it is basically the modern version of people saying that the pills they had on Saturday night were heroin-based because they felt like lounging around and chatting rather than hitting a club, or that there was acid in the pills because they had an MDA-like hallucination.

Now that you can take out a phone, visit a website that shows the results of thousands of pills from an advanced chemical testing facility that makes it clear just how unlikely that is- It has to be something more chemically complex. Fact is, people are always going to complain about MDMA quality no matter how good it is and there are always going to be careless fuckers eating 2 grams of adulterated mexedrone that 'had to be MDMA because it came from a trusted source'..

In short, there's nothing wrong with the MDMA.

 

[Jabberwocky]

sim is only useful when you're already sure what's inside and are only looking to quanify your substance. they'd never find mda or amphetamine or pma or whatever if they used sim for a random pill.

but wholly apart from that, if what you are saying were true, they also couldn't differentiate between the positional isomers ephedrine and pma (both being C10H15NO). and we know for sure that they can. if you cannot detect pma or would confuse it for ephedrine drug checking would be completely pointless.

Well they have the luxury of ephedrine and PMA being in the library -- MANY RC's and phenethylamines are not

 

[Jabberwocky]

In short, there's nothing wrong with the MDMA.

100% Agree

I was pointing out that it is more likely the GCMS was wrong (it confuses PCBs and DDT also) than it was some fantastic unknown synthesis created r-MDMA

That said, the absorption profiles of MDMA-citrate, maleate, bit-tartrate, etc. are unknown. Poor absorption or -- very slow absorption WILL cause different subjective and qualitiative experiences

 

[Black]

Well they have the luxury of ephedrine and PMA being in the library -- MANY RC's and phenethylamines are not

they also find a couple of new compounds each year. they wouldn't if they just screened for known substances.

100% Agree

me too. then let's rather try to convince those who believe their mdma is faulty

 

[aced126]

Problem Statement:

There is GCMS Tested MDMA being produced that some people identify as providing non-representative dose-response -- ie "mongy".

Hypothesis for reported observation:

The "mongy" MDMA is not the HCl salt but some other salt (fumarate, (bi)tartrate, maleate, citrate, unknown). The combination of a (significantly) higher mass salt resulting in a lower amount of MDMA per dose, coupled with lower bioavailability, and different absorption kinetics, leads to the "mongy" effects, even though the MDMA is MDMA.

None of this has anything to do with precursor. It is the step where the freebase is reacted with an acid and precipitated to crystals.

Supporting Data:

1. HCl is a very light molecule, constituting approximately 16% of a dose of MDMA

2. Fumaric acid, citric acid, and tartaric acid are not light -- in fact citrate and tartrate weigh almost the same as MDMA mole wise -- if the compound formed = bitartrate, then 200mg would only contain about 75 mg of MDMA. (~35% )

3. The HCl salt is likely ~80% orally bioavailable based on excretion unchanged, and metabolites.

4. There is no data regarding the bioavailability of other MDMA salts. However, bioavailability of mineral supplements of maleate and citrate seem to be ~60%

5. MDMA HCl is absorbed through the stomach, reasonably quickly

6. We have no data on rate of absorption for these much larger molecules. However, citrate salts are absorbed to a significant degree in the intestine.


Thoughts??

Different salts of drugs have slightly varying dissociation kinetics in solution (how fast they dissolve etc), but certain drugs are complexed with different salts for more important reasons. For example, the drug might be lipophilic and needed in a solution, so complexing the drug with a counterion will increase its solubility. Another example: different salts of drugs crystallise in different ways, and this has effects on the physical properties of the final powder/crystals of the drug (how dense it is, for example). So tinkering with the counterion can lead to optimal properties for a specific drug.

In fact in the case of MDMA, it is not used as the freebase, because MDMA freebase is a viscous oil, which makes it more difficult to handle than its hydrochloride salt, which crystallises.

However once dissolved, the drug is surrounded by solvent molecules. The counterion is also surrounded in a solvent cage. Thus once dissolved, for example in the stomach, the only important thing about the counterion salt is that it must be non-toxic and easily excretable.

Applying all these ideas to the discussion here, different MDMA salts will all have roughly the same pharmacokinetics, and thus the same physiological and mental effects. This is because the only factor affecting pharmacokinetics of drugs complexed to different salts is dissociation kinetics, which is a minor factor and all salts will pretty much dissolve next to instantly in the stomach.

***

As for different counterions having different molar weights: yes, this will result in 100mg of MDMA salt having different amounts of MDMA in them itself. However, most MDMA is complexed with HCl.

For example, MDMA makes up 84% of the mass of MDMA.HCl. If MDMA is complexed to citric acid (3 MDMA molecules to 1 citric acid molecule), then 75% of the mass of (MDMA)3.citrate is made up by MDMA. Similarly, 72% of (MDMA)2.tartrate is made up of MDMA. These differences aren't massive, and even so, chemists are very aware of this, and will adjust their prices accordingly.

Probably why most MDMA is complexed with HCl is that HCl is a low mass counterion and is non toxic. If chemists salt their MDMA with something else, such as tartrate, their product will be considered as "less pure". They can't use HF to make their product "more pure" because fluoride is too toxic, much much more than the harmless chloride.

Finally, I still think the reason why some people mong off MDMA is they've taken too much. I find it is a very narrow response curve, going from rolling nicely to rolling "too" nicely and starting to sit on sofas for the whole night.

 

[Jabberwocky]

For the record, I proposed these possible theories because they are only slightly less unlikely than a fantastical PMK-gly synth that makes bad MDMA that shows good on a GCMS test.

 

[LucidSDreamr]

it could be a salt, maybe leeched metal that is still in the purified product could be making people feel different and wouldn't show up on the standard lcms analysis