Similar to MDMA

[4DQSAR]

Do you have a TR for that? Just curious.

I've been looking for a while, there is someone who made an amphetamine from eugenol and wrote about it but i havent found it since.

It's in Pihkal.

 

[Didgital]

It's in Pihkal.

That's not what I'm referring to but thanks.
I believe there was a polish chemist who made turned the phenylpropenes Eugenol and methyleugenol into their corresponding primary and 2ndary amines, and wrote a brief pihkal like article on it. Read it years ago and haven't been able to find it since. It didn't have any crazy info just thought it was a little piece of history.

 

[4DQSAR]

That's not what I'm referring to but thanks.
I believe there was a polish chemist who made turned the phenylpropenes Eugenol and methyleugenol into their corresponding primary and 2ndary amines, and wrote a brief pihkal like article on it. Read it years ago and haven't been able to find it since. It didn't have any crazy info just thought it was a little piece of history.

Oxidative amination? Specifically photoredox-catalyzed using a single-electron transfer (PET) mechanism?

I believe someone succeeded in producing MDMA in low to moderate yields by dissolving the precursors and catalyst system in an appropriate solvent and using a very specific lighting system that produced photons of the appropriate frequency just to prove the theory. I seem to recall solvent volumes and the lighting made it an impractical route - quite novel.

It must be over thirty years since it was mentioned and I note since then a number of reagents unavailable at the time are now the preferred option. That said, are hypervalent iodine compounds still in favour? I seem to recall a few researchers discovering just how 'energetic' some of them could be.

It isn't a field I know much about but it was explained to me that the ring-substitution pattern altered the optimal frequency of the UV so while it was possible to build a setup for one specific olefin, it certainly wasn't at all versatile.

I suppose (somewhat) selective hydroxyamination was still in Barry's shed back then and if hydroboration was known, it certainly hadn't been well explored.

But if you mean olefin to amine in one step, oxidative amination is the only route I can think of.

 

[Didgital]

Oxidative amination? Specifically photoredox-catalyzed using a single-electron transfer (PET) mechanism?

I believe someone succeeded in producing MDMA in low to moderate yields by dissolving the precursors and catalyst system in an appropriate solvent and using a very specific lighting system that produced photons of the appropriate frequency just to prove the theory. I seem to recall solvent volumes and the lighting made it an impractical route - quite novel.

It must be over thirty years since it was mentioned and I note since then a number of reagents unavailable at the time are now the preferred option. That said, are hypervalent iodine compounds still in favour? I seem to recall a few researchers discovering just how 'energetic' some of them could be.

It isn't a field I know much about but it was explained to me that the ring-substitution pattern altered the optimal frequency of the UV so while it was possible to build a setup for one specific olefin, it certainly wasn't at all versatile.

I suppose (somewhat) selective hydroxyamination was still in Barry's shed back then and if hydroboration was known, it certainly hadn't been well explored.

But if you mean olefin to amine in one step, oxidative amination is the only route I can think of.

Really..

You've never heard of an oxidative cleavage of an alkene into an aldehyde and then work up using standard nitroalkane workup?

 

[4DQSAR]

Really..

You've never heard of an oxidative cleavage of an alkene into an aldehyde and then work up using standard nitroalkane workup?

Your post suggested a single step.

You certainly never mentioned any intermediate steps.

BTW NO, a nitroalkane will NOT yield a secondary amine, so well done for failing to grasp the basics. Sure, condensation of a nitroalkane and an aldehydre/ketone will yield a nitroalkene and yes you can reduce that nitroolefin directly to the primary amines using Red Al, LAH or similar or reduce to nitroalkanes with a (much cheaper) borohydride or dissolving metal reduction and then yield a primary amine with a second reduction - but it seems using the Nef reaction to yield the ring-substituted P2P is still preferred. Why? Because THEN you have the option of producing the secondary (or indeed tertiary) amine.

Go crazy - there are now chiral reductions of nitropropenes. Not perfect, the ee is only around 72% but if your product is chiral with one enantiomer being far more active, they may be worth a look. I posted the papers on the route last year.

 

[4DQSAR]

Actually 7,α-DMT is very very similar to MDA. Lest we forget, AET was sold AS MDMA so we know that indoles can be entactogens. But just as MDMA is chiral, so is 7,α-DMT. You can resolve it and it's not a surprise that (S) 7,α-DMT is a 5HT2a ligand which is why I compared the raecemate to MDA. At higher doses it becomes distinctly hallucinogenic BUT there is a window in which it is remarkably like MDA.

We resolved the two with DBTA. Uncertain if that would scale well. No idea if a radical initiator would raecemize the material.

I think we concluded that yes, if there were markets where 7,α-DMT someone could in theory produce it at a reasonable cost, the pain is in synthesizing 7-methyl-1H-indole-3-carbaldehyde. Yes, it is available as a 'fine chemical' but the prices were frankly eye-watering.

I think the value lies in recognizing that an indole system is a bioisostere of a 3-methoxy-4-methyl benzene system and looping back to Pihkal, Shulgin reported that 3-methoxy-4-methyl amphetamine turned up in Spain where it was misrepresented as MDMA at some time in the mid-70s.