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6 Chloro MDMA

wungchow

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Dec 12, 2006
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Probably neurotoxic. Just look at 6-OH dopamine. -OH and -Cl groups are generally bioisosteric in terms of how they are recognized by proteins (but obviously differ in polarity)
 

MurphyClox

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Mar 26, 2008
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A chloro substituent should raise lipophilicity IMO and, therefore, BBB-penetrability. So, if this stuff is neurotoxic (and I second wungchow here), it should be even worse 6-OH-dopamine.

Unfortunately, displacement of the methylene bridge, leaving the 3,4-dihydroxy derivative is a reported metabolism pathway. This even strengthens the proposed toxicity.

Peace! Murphy
 

MurphyClox

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Mar 26, 2008
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Not per se. As wungchow elaborated nicely, -OH and -Cl are bioisosteric. This doesn't count for the nitro-group.

Then again I would not want a nicely activated nitro-aromatic to enter my body. Geeee...

Murphy
 

Ham-milton

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Jul 20, 2007
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Ah, I think you all worry about the aromatic nitro's too much. But then again, I've never seen them used on low potency drugs.

I would let a 6-chloro or a 6-nitro-MDMA or MDA enter my body.

end of discussion.
 

mad_scientist

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Apr 20, 2006
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Remember 6-methyl-MDA is inactive, so the 6-spot may not be very tolerant to bulk. On the other hand MMDA-2 with a 6-methoxy group is active, and its N-methyl derivative too.

I would also be concerned about the toxicity of 6-chloro or 6-nitro MDMA or MDA. Why the 6-position anyway? The 5-position is more likely to be the sweet spot I'd say, 5-methyl-MDA is significantly more potent than MDA itself according to Nichols paper on it.
 
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