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20 years looking - no luck yet.

Fertile

Fertile

Bluelighter
Joined
Mar 31, 2022
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For an AGE I've sought a methodology that allows quaternary amines to be reduced to tertiary amines. Pyrolysis isn't much good although variations suggest simply heating the mixture and collecting the product. The most helpful was reaction with LAH... but LAH isn't a reagent I like. I've had bad experiences.

I mean people claim you can just use it in a dry atmosphere but how do you know when it's too humid? That hard way?

Now, I like DIBAL-H. It's bulky (for the amount of reduction it actually does), it takes an age to quench and you end up with a lot of unwanted solvent. But then again, it's a bit more forgiving

I mean if your product wholesales for £5/g then it's not worth it. If it's more like £250/g then it's worth it.
 
A chemistry board would probably be suited better for this. Shulgin's entry for DMT in TiHKAL deals with this however. Probably better to try and find an alternative route to whatever you're making instead of dealing with quaternary amines.
 
I'm nor taking of a specific reaction - I'm asking about a general reaction to convert quaternary amines to tertiary amines. It's not THAT unusual but I use a tertrmethyl anninium salt because it is the prototype of this kind of readctionl I never mentioned Shulgin neither did I consider a single case from his work.

The Sommelet–Hauser rearrangement & Stevens rearrangement are the only limited reactions I have found, The former only works when the quaternary has a benzyl amine, the latter is a secondary reaction do that the benzylamine reacts with the carbon next to the ammonium. So most certainly neither are general. The Emde rearrangement is even less use and the Hoffman rearrangement removed the ammonium and leaves an allyl with some propenyl thrown in.

So I HAVE looked in sine detail.

It just seems odd that the Menshutkin reaction was well established and yet nobody foind a method to go the other way,

I admit that the body uses quaternary ammonium compounds a lot which suggests they are stable.
 
Fertile said:
I'm nor taking of a specific reaction - I'm asking about a general reaction to convert quaternary amines to tertiary amines. It's not THAT unusual but I use a tertrmethyl anninium salt because it is the prototype of this kind of readctionl I never mentioned Shulgin neither did I consider a single case from his work.

The Sommelet–Hauser rearrangement & Stevens rearrangement are the only limited reactions I have found, The former only works when the quaternary has a benzyl amine, the latter is a secondary reaction do that the benzylamine reacts with the carbon next to the ammonium. So most certainly neither are general. The Emde rearrangement is even less use and the Hoffman rearrangement removed the ammonium and leaves an allyl with some propenyl thrown in.

So I HAVE looked in sine detail.

It just seems odd that the Menshutkin reaction was well established and yet nobody foind a method to go the other way,

I admit that the body uses quaternary ammonium compounds a lot which suggests they are stable.
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Thats a great substitute for some grindards if the reagents aren't too expensive and are legal lol
 
Oh I'm not considering illegal.

What I am doing is working through possible prodrugs. Stuff so simple that simply boiling in water for 1 hour would render it legal.
I notice N-formal amphetamine is not listed (reflux in HCl).

N-acetyl amphetamine doesn't seem to have been controlled.

I'm also interested to know if someone takes a prodtug, smokes it like crack or on foil and it's converted to active, exactly WHO is making the active.
The UK psychoactive substances act is REALLY over-reaching. 'Any compound if consumed that has a psychoactive effect' is automatically controlled. Well their are a HUGE number of dual-use compounds but they carefully weasel out of them.

If it has an obvious other use.... it's exempted...
 
they are illegal though. Just because a drug has a protecting group on it does not mean it magically became legal. Its still highly illegal
 
TripSitterNZ said:
they are illegal though. Just because a drug has a protecting group on it does not mean it magically became legal. Its still highly illegal
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but it has a protecting group lol that will help protect it from the law, I personally recommend 9-Fluorenylmethyl carbamate (Fmoc-NRR')
 
TripSitterNZ said:
they are illegal though. Just because a drug has a protecting group on it does not mean it magically became legal. Its still highly illegal
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Yeah - try reading UK law. The US isn't the only nation on earth,
 
IIRC both L-selectride and lithium triethylborohydride have been used for this purpose.
 
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