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 Once it's been o-demethylated to HHMA, it is no longer active like MDMA is.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 · 1 points
She wasn't on any other medications nor was she mixing with anything other than what she was taking. She also took the same amount as everyone else. No history of mental illness as well. That's what's so confounding about the whole thing. I know there are a few psychedelic amphetamines that last upwards of 2-3 days depending on the dosage, but no one else had any ill side effects. I know that a marquis test can't rule out other things, but I was just making a statement that we believed we were working with relatively pure MDMA. That's what's so weird about the whole thing.
I've been awake for upwards of days on cathinones or amphetamines before and I never really had any heavy amphetamine psychosis. I know the same can't be said for everyone else, but she seemed like she was in a state of psychosis from around the time everyone came down and gradually became worse.
u/MisterYouAreSoDumb
That's strange! Especially since you all took the same thing. What was the dosage? Did she re-dose? Did she eat a lot of dark chocolate (it's an MAOI)? Has she taken MDMA before without issues? I can't rule out the possibility of a genetic disorder that caused an issue. Perhaps she has higher levels of CYP3A4, which gave her high serum levels of MDA. It binds to your 5-HT2 receptors and is psychedelic. Still though, 4 days is crazy!