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Do you think it is safe to consume 3 years old MDMA?

Migrated topic.

Noisy

Rising Star
The question is in the topic title!
I have to say this MDMA had been kept in the freezer, in aluminium foil, never opened during those 3 years.
Do somebody here have an idea of MDMA molecule stability throughout time?
 
Shulgin was once quoted as saying that if MDMA existed in ancient egypt and had been kept in the pyramids it would still be active today. Keep it dark and dry and it's good for longer than you'll be alive.


I ate a couple 13 year old beans I found in my "memory" box a couple months ago. Triple stack blue dolphins. They rocked my world.
 
An interesting study on the topic, though it doesn't get into anything very long term, it does explore various temperatures and mediums:

Stability study of the designer drugs "MDA, MDMA and MDEA" in water, serum, whole blood, and urine under various storage temperatures.
Clauwaert KM1, Van Bocxlaer JF, De Leenheer AP.

Abstract
A controlled study was undertaken to determine the stability of the designer drugs MDA, MDMA and MDEA in pooled serum, whole blood, water and urine samples over a period of 21 weeks. The concentrations of the individual designer drugs in the various matrices were monitored over time, in the dark at various temperatures (-20, 4 or 20 degrees C), for a low (+/- 6 ng/ml for water, serum and whole blood and +/- 150 ng/ml for urine) and a high concentration level (+/- 550 ng/ml for water, serum and whole blood and +/- 2500 ng/ml for urine). Compound concentrations were measured using a validated HPLC assay with fluorescence detection. Our study demonstrated no significant loss of the designer drugs in water and urine at any of the investigated temperatures for 21 weeks. The same results were observed in serum for up to 17 weeks, and up to 5 weeks in whole blood. After that time, the compounds could no longer be analyzed due to matrix degradation, especially in the low concentration samples that were stored at room temperature. This study demonstrates that the designer drugs, MDA, MDMA and MDEA are stable when stored at -20 degrees C for 21 weeks, even in haemolysed whole blood.


MDMA is an alpha-methyl-phenethylamine, and phenethylamine molecules are known to be quite stable, there have even been samples of a related molecule, 3,4,5-trimethoxyphenethylamine, that remained stable over thousands of years*, the plant material in which this 3,4,5-trimethoxyphenethylamine amoung other alkaloids was found was said to be some of the oldest material ever subjected to an alkaloid test, and it's contained phenethylamines were still intact.

*
Peyote alkaloids: identification in a prehistoric specimen of lophophora from coahuila, Mexico
Abstract
Mescaline, anhalonine, lophophorine, pellotine, and anhalonidine have been identified in alkaloid extracts of a prehistoric specimen of Lophophora from a burial cave in west central Coahuila, Mexico. The specimen is associated with radiocarbon dates of A.D. 810 to 1070 and is one of the oldest materials ever submitted to alkaloid analysis.

Peyote alkaloids: identification in a prehistoric specimen of lophophora from coahuila, Mexico - PubMed

-eg
 
I'd worry about that methylene dioxy ring falling apart though. It's stabilized by the adjacent aromatic structure, but looking at it, I'd expect that it would probably fall apart into ortho hydroxyl and methoxy groups, esp. if exposed to heat or ambient moisture.

Whether the resulting compound is active or toxic, I have no idea. That hydroxyl group would probably inhibit crossing of the BBB though.

Blessings
~ND
 
Nathanial.Dread said:
I'd worry about that methylene dioxy ring falling apart though. It's stabilized by the adjacent aromatic structure, but looking at it, I'd expect that it would probably fall apart into ortho hydroxyl and methoxy groups, esp. if exposed to heat or ambient moisture.

Whether the resulting compound is active or toxic, I have no idea. That hydroxyl group would probably inhibit crossing of the BBB though.

Blessings
~ND

Hmmm...

In the situation which you described An open hydroxyl group most likely would act as a giant, polar, hydrophilic lump, making passage across the blood brain barrier quite difficult, or impossible, very few compounds with a free hydroxy group are able to cross the blood brain barrier...so in this case even though the N-methyl-amphetamine core would remain, your degradation product could be inactive...

Looking at compounds such as 4-methoxy-N-methyl-amphetamine, which could be considered similar to your proposed degradation product, it does not look hopeful that degradation products of this type ( leaving hydroxy or methoxy groups at 3 and or 4 where the methylenedioxy ring broke) would yield anything desirable:

4-methoxy-N-methyl-amphetamine (with 110 mg) One hour into it, my pulse was up over 100, and I was compulsively yawning. There was some eye muscle disturbance, a little like the physical side of MDMA, but there was none of its central effects. But all the hints of the cardiovascular are there. By the fourth hour, I am pretty much back to baseline, but the yawning is still very much part of it. I might repeat this, at the same level, but with continuous close monitoring of the body. PIHKAL ; shulgin

Though anecdotal evidence suggests that poorly stored MDMA which was thought to have degraded produces neither positive or negative effect, and at least appears to be benign and inactive.

it's fascinating to see how the body dismantles the molecule:

MDMA metabolism is rather complex and includes 2 main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine.

Though more information on the molecules degradation otherwise would be great...

-eg
 

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A lot of theory here and you guys are the real chemists not me...

But in practice, MDMA is very stable, ive tested samples that were years old stored just in a drawer and there was not a hint of degradation.
 
endlessness said:
A lot of theory here and you guys are the real chemists not me...

But in practice, MDMA is very stable, ive tested samples that were years old stored just in a drawer and there was not a hint of degradation.
Especially when the stuff has been stored in the freezer for three years. Yes, it's safe.
 
I'm a Chemistry student, well, I stopped school momentarily, but I still study and do apprenticeship work in the chemistry field, I'm still learning, and I still have a good deal to learn.
It would be nice if the chemists with more experiance and education would join in and set things straight from time to time, we know who you guys are and will listen without arguments. I'm a very skeptical and argumentative person naturally, and I always have a lot of questions, but I can suppress it, I'm more interested in learning, rather than building a reputation or socializing. I will gladly embarrass myself by asking questions which I "should" know, but had trouble understanding in school or in independent research, if by doing so I will be able to obtain some answers.

Orbitals are for mathematicians – Organic chemistry is for people who like to cook ! -Alexander shulgin

-eg
 
dragonrider said:
endlessness said:
A lot of theory here and you guys are the real chemists not me...

But in practice, MDMA is very stable, ive tested samples that were years old stored just in a drawer and there was not a hint of degradation.
Especially when the stuff has been stored in the freezer for three years. Yes, it's safe.


And here is the experimental confirmation: this MDMA sample stored in my freezer was as potent as the day I acquired it. I clearly felt 60mg of this product, with no adverse effects, except hyperdiuresis, but that was linked to the gram of mushroom I took with (I'm really fond of this association, I will try to write a trip report during my next hollidays)
 
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