Comment · Thu, November 22, 2012
MDMA Neurotoxicity Part 1 Metabolites)
Original post in this thread
MisterYouAreSoDumb · 129 points
This is probably going to be the first in a series of discussions I start about MDMA. There's just too much information for one post. Therefore, I am going to start with one that is very interesting to me: MDMA's metabolites and their role in neurotoxicity. I pre-appologise for the length and terminology used.
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First off, let's discuss how MDMA is metabolized. The human cytochrome CYP450 is responsible for the metabolism of MDMA. The primary enzyme responsible is CYP2D6, using O-demethylation. This process adds two hydrogen atoms to the two open oxygen atoms in MDMA to create HHMA. Let's look at the structure for a minute.
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MDMA is 3,4-methylenedioxy-N-methylamphetamine
HHMA is 3,4-dihydroxy-N-methylamphetamine
So your CYP2D6 enzyme added two hydrogen atoms to the methylenedioxy structure to create a dihydroxy structure. Once it's been o-demethylated to HHMA, it is no longer active like MDMA is. HHMA can then be 0-methylated further to HMMA, or 4-hydroxy-3-methoxy-N-methylamphetamine. Here is an image to help you visualize this process.
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What they were answering
iamabill · 2 points
You talked about a lack of a certain enzyme that caused possibly fatal reactions. I ask this question a little nervously out of fear of being called a liar or uneducated, but I had experience with a girl once that literally did not come down. It WAS MDMA and was marquis tested. It eventually ended after 4 or so days without sleep after the cops were called because she crawled out of window completely nude. She was sedated and eventually woke up fine. Given these circumstances do you think it was a lack of a certain enzyme that delayed the metabolism of the drug?
u/MisterYouAreSoDumb
Ohh no, there is no way you could sustain a roll for 4 days. Just because it tested positive for MDMA with the marquis test, does not mean that there was not something else in it. Even so, 4 days is nuts. Not sure what that would be. The MDMA would be out of her system by then, or completely metabolized into other substances. Can you give some more details on the situation? Perhaps it was an interaction with something like an MAOI that led to amphetamine psychosis.