Methylenedioxymethamphetamine

[Thug Love]

I think Methylenedioxymethamphetamine, also known as MDMA; of course, is one of the most hydrastinine chemicals in America. Now one of my fellow colleagues dissagreed with me! Your resonse?

 

[Ham-milton]

What the hell do you mean by "hydrastinine"??? MDMA isn't hydrastinine, and isn't even from the same family (it's a THIQ).

I suppose you could claim that it's a conformationally constrained analogue, but unlike MDMA, hydrastinine is inactive (Nichols, personal communication).

Oh, here's the structure:

Now MDMA:

 

[Riemann Zeta]

Wow, someone set him up the bomb. Either that is some spectacular AI engrish, or the OP was 'totally tripping balls.' The chemical hydrastinine is pretty interesting, though. I'm not surprised it is inactive--where is the alpha-methyl group? It is not an amphetamine without the "am" moiety. I wonder what the methylenedioxy analogue of phenmetrazine is like?

 

[Ham-milton]

I don't think a methyl properly located would make it active. I think the N-methyl needs to go first.

 

[djfriendly]

This is too advanst for me.

 

[Riemann Zeta]

Yeah, the N-methyl has to go too. Reminds me of phendimetrazine--make it a tertiary amine and it is totally inactive (luckily the metabolite is active).

 

[Thug Love]

Hm...Interesting. I'll take note of that diagram. Any other thoughts on this or?

 

[Acyl]

Reflux that chem in a conc base solution to give you the MDMA structure with an aldehyde at C-6.

Im sure people here can make educated/uneducated guesses at its activity