phase_dancer
Bluelight Crew
PMA & MDMA; a new look at an old devil
News articles highlighting the dangers of ecstasy often claim PMA is a contaminant in MDMA. Paul Dillon was once quoted as saying PMA was produced from side reactions during synthesis, but no satisfactory explanation was offered which described how his occurred. Biscuit and I have argued against the idea that para-methoxy amphetamines could be produced from safrole via opening of the methylenedioxy bridge, as this would seem impossible with conditions normally employed in typical MDMA syntheses. Even if this did happen, no significant amount of PMA would be produced, as the amine used in producing MDMA is methylamine which would instead produce the N-methyl product PMMA.
However, unlikely as it is that PMA would be present as an impurity in MDMA, a recent article on establishing profiling parameters for forensic testing of Ecstasy indicates PMMA is a characteristic contaminant in MDMA. In fact, PMMA is a route-indicating impurity used by forensic chemists to determine such things as the method of synthesis and starting materials.
So where does the PMMA come from?
The answer is that it simply comes from sassafras oil - principle source of safrole - via another constituent of the oil known as anethole. Although distillation is required to separate the safrole from the other components of the oil, it would be impossible to completely separate anethole from safrole with distillation, as the boiling points are too close.
Boiling Point of Anethole = 233-235 deg C
Boiling Point of Safrole = 232-234 deg C
Boiling Point of Isosafrole = 253 deg C
Look, it really does get through!
Besides the characteristic ring substitutions (red = methylenedioxy for MDXX & blue = para-methoxy for PMXX) Safrole is also different to anethole in that safrole has a terminal double bond involving second and third (end) carbons in the alkyl chain, whereas anethole has the double bond between the first and second carbons of the alkyl side chain like isosafrole. With routes to MDMA involving the ketone, it is usually required that the safrole be first isomerised to isosafrole. Any anethole present at this stage would sit quite comfortably through the safrole isomerisation process.
What about purification of Isosafrole?
Isosafrole is to MDMA what Anethole is to PMMA, but as stated anethole has a boiling point around that of safrole which means most should be removed by fractional distillation of the isosafrole. This explains the absence of anethole in the commercially produced ketone.
Impurities in Commerically available MD2P2
However, if during an MDMA synthesis the isosafrole was not sufficiently purified (as could be expected with some clandestine labs) any anethole would then be processed via the same routes intended for the isosafrole, with the PM products passing through purification processes to produce PMMA as part of the final product. Of course if MDA was made instead of MDMA, the corresponding paramethoxy amine produced from the anethole would be PMA
But how dangerous is all this?
To keep things in perspective, even if techniques were very sloppy, it is not thought the total amount of PMMA or PMA synthesised would amount to little more than a small percentage of total amine produced (
% IMO). While literature lists anethole as one of the major constituents of sassafras oil, the actual percentage is low compared to the active ingredient safrole. I would then think it unlikely that levels of PMMA found in street MDMA would be high enough to be of great concern to immediate health, but I couldn’t say for sure on this.
Other Goodies
PMMA is only one of the commonly found contaminants in MDMA. Another allyl-benzene present in safrole produces 3,4DMMA. This compound is also probably active, but would not be thought to be present in large enough quantities to cause any effect.
In all, mixtures of any of these compounds – including many toxic, non-active chemicals - are present in all MDMA. Although they should only be present in very small amounts, one can’t help but wonder if the roll is ever affected by them.
Open to all scrutiny
phase_dancer
Other References ;
http://sun.ars-grin.gov/cgi-bin/duke/chemical.pl?ANETHOLE
http://www.erowid.org/library/books_online/pihkal/pihkal055.shtml
-(thanks to Rhodium for the forensics article)-
News articles highlighting the dangers of ecstasy often claim PMA is a contaminant in MDMA. Paul Dillon was once quoted as saying PMA was produced from side reactions during synthesis, but no satisfactory explanation was offered which described how his occurred. Biscuit and I have argued against the idea that para-methoxy amphetamines could be produced from safrole via opening of the methylenedioxy bridge, as this would seem impossible with conditions normally employed in typical MDMA syntheses. Even if this did happen, no significant amount of PMA would be produced, as the amine used in producing MDMA is methylamine which would instead produce the N-methyl product PMMA.
However, unlikely as it is that PMA would be present as an impurity in MDMA, a recent article on establishing profiling parameters for forensic testing of Ecstasy indicates PMMA is a characteristic contaminant in MDMA. In fact, PMMA is a route-indicating impurity used by forensic chemists to determine such things as the method of synthesis and starting materials.
So where does the PMMA come from?
The answer is that it simply comes from sassafras oil - principle source of safrole - via another constituent of the oil known as anethole. Although distillation is required to separate the safrole from the other components of the oil, it would be impossible to completely separate anethole from safrole with distillation, as the boiling points are too close.
Boiling Point of Anethole = 233-235 deg C
Boiling Point of Safrole = 232-234 deg C
Boiling Point of Isosafrole = 253 deg C
Look, it really does get through!
Besides the characteristic ring substitutions (red = methylenedioxy for MDXX & blue = para-methoxy for PMXX) Safrole is also different to anethole in that safrole has a terminal double bond involving second and third (end) carbons in the alkyl chain, whereas anethole has the double bond between the first and second carbons of the alkyl side chain like isosafrole. With routes to MDMA involving the ketone, it is usually required that the safrole be first isomerised to isosafrole. Any anethole present at this stage would sit quite comfortably through the safrole isomerisation process.
What about purification of Isosafrole?
Isosafrole is to MDMA what Anethole is to PMMA, but as stated anethole has a boiling point around that of safrole which means most should be removed by fractional distillation of the isosafrole. This explains the absence of anethole in the commercially produced ketone.
Impurities in Commerically available MD2P2
However, if during an MDMA synthesis the isosafrole was not sufficiently purified (as could be expected with some clandestine labs) any anethole would then be processed via the same routes intended for the isosafrole, with the PM products passing through purification processes to produce PMMA as part of the final product. Of course if MDA was made instead of MDMA, the corresponding paramethoxy amine produced from the anethole would be PMA
But how dangerous is all this?
To keep things in perspective, even if techniques were very sloppy, it is not thought the total amount of PMMA or PMA synthesised would amount to little more than a small percentage of total amine produced (
% IMO). While literature lists anethole as one of the major constituents of sassafras oil, the actual percentage is low compared to the active ingredient safrole. I would then think it unlikely that levels of PMMA found in street MDMA would be high enough to be of great concern to immediate health, but I couldn’t say for sure on this. Other Goodies
PMMA is only one of the commonly found contaminants in MDMA. Another allyl-benzene present in safrole produces 3,4DMMA. This compound is also probably active, but would not be thought to be present in large enough quantities to cause any effect.
In all, mixtures of any of these compounds – including many toxic, non-active chemicals - are present in all MDMA. Although they should only be present in very small amounts, one can’t help but wonder if the roll is ever affected by them.
Open to all scrutiny
phase_dancer
Other References ;
http://sun.ars-grin.gov/cgi-bin/duke/chemical.pl?ANETHOLE
http://www.erowid.org/library/books_online/pihkal/pihkal055.shtml
-(thanks to Rhodium for the forensics article)-
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