Methylenedioxyphendimetrazine (MDPDM, RMDMA)

[MagickalKat777]

[Original title: 2-(benzo[d][1,3]dioxol-6-yl)-3,4-dimethylmorpholine (RMDMA)
Other IUPAC names: 2-(benzo[d][1,3]dioxol-5-yl)-3,4-dimethylmorpholine, 2-(3,4-methylenedioxyphenyl)-3,4-dimethylmorpholine]

Okay, we had a post about this appear in MED a few days ago but it was closed due to the content of the original post, however, since this is likely a real chemical, I'm making a thread here so that discussion can commence.

Anyone have any ideas about this one?

EDIT: It may well be an incorrect name.

I found 2-(benzo[d][1,3]dioxol-5-yl)-3,3-dimethylmorpholine on Google. Interesting structure. Don't really know anything about it though.

That's the 5-yl/3,3 I found.

 

[Black]

so we're looking at this structure?

i'd assume that the iupac name given in the title is the correct one, as this one has "mdma in it".

i don't think it's active. shulgin didn't exactly find activity with just sticking only an additional methyl group on the N and this thing is more bulky. besides, doesn't the nitrogen need to be oriented in the following way (which isn't possible here) to be active for empathogens?

 

[Solipsis]

Yeah that's the one I figured as well:"

2-(benzo[d]1,3-dioxol-5-yl)-3,4-dimethylmorpholine /
2-(1,3-benzodioxol-5-yl)-3,4-dimethylmorpholine

Also that 4-methyl doesn't seem like the wisest decision in designing this drug but that is a matter to be discussed in an actual thread.

it seems the 6-yl part is incorrect - unless you count differently once the benzodioxolyl is considered a whole, for some reason - but anyway that is not really important. Black you raise very good points, if what you're saying is true this goes beyond the amine being tertiary.

Hold on though, I think you can still twist the molecule your way.. let me draw it.

Here:

(sorry it's a little sucky - I seem to have messed up my settings, it was almost like my chemsketch had comic sans by default lol)

Don't really know whether to correctly call that morpholine to be in a chair or boat conformation but hey.

I think that the orientation is possible after all, right?

 

[sekio]

This drug is "methylenedioxy phendimetrazine".

This compound has 2 chiral centres and hence can exist as 4 possible isomers, the "skeletons" being (+)/(-) phen(di)metrazine (trans) and (+)/(-) pseudophen(di)metrazine (cis). More of the activity resides in the (+) isomers, so the most active is (2S,3S) or (+)-trans-3-phenyl-2(,4-di)methylmorpholine. Luckily, commercial synthesis likely results in predominantly trans (more active) product if it comes via the ephedrine analogue.

The morpholine ring exists in a chair conformation. N' methyl to the bottom left, 2' methyl to the bottom right.

Like phendimetrazine, the N-methylation will probably destroy most direct stimulant activity. Secondary amines are best for stims it looks like (c.f methamphetamine > amphetamine >> N,N-dimethylamphetamine in potency), and phendimetrazine is treated like a prodrug.

Probably a better drug is the N-demethylated analogue. It would very likely be a nice NDRI. This probably lacks most of the activity of MDMA in the serotonin department. The other related cyclic drug I can think of like this is the active metabolite of buproprion.

http://www.ncbi.nlm.nih.gov/pubmed/12106802
http://www.ncbi.nlm.nih.gov/pubmed/23211394

 

[Black]

Don't really know whether to correctly call that morpholine to be in a chair or boat conformation but hey.

I think that the orientation is possible after all, right?

the way you've drawn it looks like the twist conformation to me. and yes, it seems to be possible. but i'm not sure if it likes being orientated in this way, i'm too tired to wrap my head around the 3d structure right now without having a physical model to fumble around with

 

[Solipsis]

Now that you put it like that, looks comfy

If it's not going to be a good serotonergic agent, what good is the methylenedioxylation? Or is that a bit discriminating since there are plenty of stims along the direction of MDPV that have potential in their own right, if that's your cup of tea?

So... how much sense would p-methylphenmetrazine make?

@Black: do you mean something like this: http://en.wikipedia.org/wiki/3,4-Methylenedioxy-1-benzylpiperazine ?
Ahh no sorry I see now what you explicitly meant with the 2-pos sub. No idea about them, what would be the parent (2-phenylpiperazine itself) is not giving me any results.

 

[Black]

considering how methylone compares to mephedrone, i think the methylenedioxy would be preferable

@Black: do you mean something like this: http://en.wikipedia.org/wiki/3,4-Methylenedioxy-1-benzylpiperazine ?
Ahh no sorry I see now what you explicitly meant with the 2-pos sub. No idea about them, what would be the parent (2-phenylpiperazine itself) is not giving me any results.

it doesn't really matter anyway now, since sekio found phendimetrazine, so we now know that the N at that position at least fits into the amphetamine SAR, and doesn't have piperazine-like qualities.
still, by moving the N one position we'd probably get some kind of activity at various 5-ht receptors (or serotonin release), but i really don't think that it would lead to something remotely good, especially when considering how poor a drug MDBZP is even compared to other phenylpiperazines.

 

[gookma]

My friend just received 50g of this chem of Chinese origin. He will be performing a reagent test first possible chance, most likely in a few hours. Ill get pictures of his test and post results. He will also be ingesting some tomorrow night.

Pretty sure the chem in question is Ethylone. mix up with the order...damnit...

 

[wzrd420]

I recieved a sample of this but what exactly is IT? I've heard it's 2-ptc as another name.

 

[ebola?]

totally unrelated compound.
...
So wouldn't we expect this compound to be a releaser?
And why did they produce this rather than the phenmetrazine homologue? Phendimetrazine is essentially a prodrug for phenmetrazine, and this is not a quality that is desired in a potential 5ht releaser.

ebola

 

[sekio]

I suppose it would indeed be a releasing agent. Interesting.

 

[wzrd420]

then how do I know what I got is R'mdma not 2-ptc since some vendors sell them under the same name.

 

[Solipsis]

You might ask for a formula to clarify, but honestly I don't think I would like to take any chances with such a vendor if there is a risk involved that they ship you 2-PTC.
I am shopping for etizolam but will probably even choose another vendor than one I had my eye on, since that one also sells different phenylcyclopropylamines.

 

[wzrd420]

it's smells of safrole would 2-ptc even smell like that?

 

[bob_arctor]

still, any initiatives in the field of bringing possibly worthwhile phenmetrazine analogs to the stamp collectors. interesting.