β-MeO-MDMA

[Solipsis]

I just saw that a vendor is expecting this compound, although I highly doubt it is legitimate. Still I am curious about any information you have on this:

3,4-methylenedioxy-β-methoxy-N-methylamphetamine

IUPAC: 1-(benzo[1,3]dioxol-5-yl)-1-methoxy-(N-methyl-)propan-2-amine (/ 1-(benzo[1,3]dioxol-5-yl)-1-methoxy-2-methylaminopropane ?)

 

[electrodevo]

Well, it's essentially methylone... with a methyl group bonded to the *oxygen* of the carbonyl? Is that even chemically possible? (Maybe somewhere, I'm sure, but the more "typical" reaction I see is more like attaching a methyl to the carbon of the former C=O bond, among others...)

If this compound was real, I would doubt it would be too effective (methylone with more dangly bits, yay, typically dangly bits make for weaker MDxx compounds). But I imagine it's not real anyways.

 

[ebola?]

Mmmm...given Shulgin's results exploring the BOx series, I would expect this compound even less potent and more adrenergic than M1.

ebola

 

[Solipsis]

Oh yeah beginner's mistake, I also checked and amines have priority over ethers as well so the base structure is not really named after the ether and the methoxy stays a substitution. I am just not sure how to put the N-methyl...

Thanks for the feedback, I figured as much regarding the probable adrenergic qualities, vasoconstriction and other sympathomimetic body load related side-effects... I guess it isn't really a wonder that this one isn't more popular or known. When I first saw it for a second I thought it was related to FLEA which I recall to possibly be nice... but of course it is quite unrelated.

 

[Incunabula]

I have tried BOD, and compared to 2CD it was much longer lived, but also less stimulating and less psychedelic, Deffinitely more potent. Anyway yeah, I'm not so sure about the idea that beta-methoxy is going to make a phenethylamine more "adrenergic".

I know BOD/2CD are psychedelics and MDMA is more a stimulant, so comparisons can't really be made, but still.

I'm sure this compound won't be as good as MDMA, but it's probably active and some people will always think it's worth taking.

Interesting why it hasn't been made before. Is it difficult to synth?

 

[sekio]

definitely harder to make than methylone or MDMA.

 

[Deinonychus]

...I am just not sure how to put the N-methyl...

I would have thought 1-(1,3-benzodioxol-5-yl)-1-methoxy-2-(methylamino)propane, but checking against my chemdraw, that's wrong too and instead it is (1-[1,3-benzodioxol-5-yl]-1-methoxypropan-2-yl)(methyl)amine. I'm guessing that scheme of parentheses comes from there being only one position (two bonds, but both would be at the N-) of substitution on an amine, the nitrogen, so if the amine is the stem then the Ns are dropped? Kinda skeptical of this still, I've not known chemdraw to get it wrong but I'd see if somebody with a more authoritative knowledge of IUPAC agrees.

 

[Hammilton]

There shouldn't be the parentheses around the methyl. There will never be a group in parentheses without a position identified immediately preceding it. I'm pretty sure your first identification is correct.

How did you obtain that? There's no way ChemDraw spat out that name. If that was the name you entered to get the correct structure, don't make a conclusion based on that. ChemDraw has the option to display the structures name if you right click on a completely selected structure. Don't have only part selected, though or you'll get the name of some fragment.

 

[Deinonychus]

My mistake actually, it's Marvin, not chemdraw, so the name algorithm may be subpar. Oddly enough that first try was what I input into the 'import name' function, where you give it an IUPAC name and it makes the structure, and the structure it made was correct for beta-MeO-MDMA. And then I went straight to the 'calculate naming' function with the whole molecule selected, expecting it to spit back out the same name, and it have me the weird, extra-parentheses version.

I'm putting this down to shitty naming algorithm relative to chemdraw then. Glad to know my first human-powered guess was better than the machine-generated version for once!

 

[Dresden]

To me, that molecule looks like it's worth a try at least.

 

[Hammilton]

It's worth a try. But that's it. It's nothing more than a novelty to check off a list.

 

[bloodshed344]

It's worth a try. But that's it. It's nothing more than a novelty to check off a list.

Since this is ADD, it comes with the territory to ask what could this substitution position have to offer?

What is possible and what is desired?

What of B-Methyl MDMA or B-Methyl N-Methyll 3,4 - methylenedioxyphenethylamine (considering a methyl at the beta position would help prevent breakdown just like a methyl at the alpha position right?)

or B-Ho MDMA...

are halogen substituents at this position possible. B-Fluoro-MDMA?

I expect of course that my first few suggestions would be no good, but B-Fluoro MDMA? Now that sounds good, if a bit impossible.


sorry for my advanced drug speculations without the advanced drug knowledge.

 

[atara]

This beta-methoxy thing is an ether, which seems to indicate that it would be hard to form, but this is far from the case. The synthesis is surprisingly facile! Of course, the mere possibility does not mean that the lab is being honest.

It's worth a try. But that's it. It's nothing more than a novelty to check off a list.

Are you certain of this? The ether functionality is not too rare in SRAs cf indeloxazine, I wouldn't be so quick to doubt this thing.

http://www.erowid.org/library/books_online/pihkal/pihkal015.shtml

Perhaps alpha-methylation will be good.

My guess for the synthesis would be [edit: some stuff I can't discuss on bluelight]

 

[ebola?]

As a quick reminder, when you begin talking about a multi-step process involving the application of reagents, you are stumbling into synthesis discussion.

ebola

 

[Psychedelic Jay]

Is this another case of “Close, but no cuban”?