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New MDMA substitute... anyone have more info?

wungchow

wungchow

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I heard from a trusted source that this molecule exerts MDMA-like effects in man (SERT reversal being one of them..) I haven't been able to find any more info.

Thoughts?
 

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Something about that molecule just doesn't sit right with me. That alkene looks like trouble. Also, is there a name for this molecule (other than the hideous (Z)-6-(benzo[d][1,3]dioxol-4-yl)-N-methylhex-5-en-2-amine algorithmic name)? How do you know that it is a SERT substrate?
 
looks scary with that alkene, agreed.

I can't find anything about it. If there's a paper, post it at Blacklight please!
 
The alkene will be needed to hold the chain in the correct orientation so that spacially the methylamino group is in the same place, relative to the aromatic ring as the methylamino group of MDMA, so the structure makes sense. Wouldn't worry about the alkene too much as the molecule has a big, fuck off polar 'handle' in the methylamino group that will facilitate clearance/elimination well before any epoxidation of the double bond occours.

Fuck knows what the metabolites will be & how they will impact on dopaminergic & serotonogic neurones (always the possibility that it will have a weird metabolic offshoot & produce some nasty compound like the neurotoxic 2,4,5-trihydroxyphenethylamine), but I suppose if nothing toxic is produced it'll have the distinct advantage over MDMA in not having alphamethyldopamine as a metabolite!
 
My concern with the alkene was the decreased halflife and resulting metabolites.
 
wow, interesting! has any human ever tried this? is there a common name for it?

i wonder if other amphetamine analogs using this design as a template would retain activity (maybe PEA analogs would be active too?).
 
I would imagine. Synapse compared this one and MDMA with MM2 mimimization and the 'tail' ended up on the MD side. That doesn't bode well, I'm afraid.

The 1,2-MD-5-(1-methylaminoethyl)napthalene suggested by LuxEtVeritas was as perfect as you can get though. It's a lot easier to argue that that napthalene is an MDMA analogue, though.
 
Ham-milton said:
My concern with the alkene was the decreased halflife and resulting metabolites.
Click to expand...

How do you see the double bond decreasing the half life? As I mentioned, the amine group will allow for renal clearance etc long before anything happens to the alkene function (still that is no guarentee that it will not produce ugly, toxic metabolites by opening the methylenedioxy ring and or conjugation/demethylation of the methylamino group


wonder if other amphetamine analogs using this design as a template would retain activity
Click to expand...

Now that's the sort of creative thinking I can appreciate :D
 
Actually, I think it might be a better fit than I first thought (and than the MM2 simulation would predict)--if that alkene keeps its nose clean and stays out of trouble, we may have something interesting here. Here is a molecular overlay of the compounds using MMFF94 energy minimized 3D structures--the overlay was performed with flexible bonds were applicable and the molecules were parameterized with CHARMm force fields. The second pic is an overlay of the solvent-accessable (H2O) electrosteric fields, with MDMA in blue and fake MDMA in yellow.
 

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Without revealing too much sensitive information, my colleague tells me he has synthesized this molecule (albeit low yield) and has tested it in sub-milligram doses.. all good so far... I basically heard about this whole project from a friend who is a wanna be Shulgin (and damn good organic chemist.) If I'm lucky I may be able to post some synthesis steps at blacklight.
 
Please include dosage and duration information if you have it. I'm curious.
 
Riemann Zeta: What software did you use to produce that? Looks nice :) .
 
wungchow said:
Without revealing too much sensitive information, my colleague tells me he has synthesized this molecule (albeit low yield) and has tested it in sub-milligram doses.. all good so far... I basically heard about this whole project from a friend who is a wanna be Shulgin (and damn good organic chemist.) If I'm lucky I may be able to post some synthesis steps at blacklight.
Click to expand...


all good meaning he has seen some characteristics effects I assume? I would posit it is a good deal more potent...

or all good meaning he is not dead or in a delirium 8o ;) =D

in regard to legal status (US) just for hypothetical analysis and discussion an interesting note is that being it is not even a phenethylamine/AMPH how 'analogous' is it really?
 
...and it would be real interesting if this or any related structures had a superior subjective overall effect to the gold standard MDMA as most all subjectively similar analogues fall well short

anyway keep us updated as well curious on that and half-life et al..
 
Is it CIS or TRANS? (or both)

The CIS version looks something akin to an unconstrained alpha-methyl-6,7-substituted tryptamine analogue (missing the NH on the indole). [The image is probably more clear than that sentence!]

http://en.wikipedia.org/wiki/Alpha,N-DMT
 

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hi, i know this thread is old n probably more than a bit dead. i was wondering if anyone had any new info on the compound, it looks really interesting potentially n new class of hybrid drugs between the pea n tryptamines, depending on the cis trans isomerism. pandoras box (filled with delights) :). id really appreciate it if anyone could give me any info regarding this or similar, dose, effects etc
thanx!

ps if i had a lab id synth some, then get it toxilogically tested for anything too obviouse, id also send it to a lab with nmr etc to see the structure n purity of the compound, expensive i know but good none the less. thats if i had a lab... one day....
 
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Shape...

It looks to me like the compound may be an interesting one as well. The Tryptamine similarities are quite striking. I wonder if you removed the MDO if it would behave like a,N-DMT? (Based on the side by side above)
 
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