Author Topic: IAA --> AET  (Read 10195 times)

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psyloxy

  • Guest
IAA --> AET
« on: May 18, 2000, 05:44:00 PM »
Everyone knows that PAA can be turned into P2P with Ac2O.
So why couldn't one use IAA (indole-CH2-COOH) and propionic anhydrite to make "AET-P2P" ?

"Amphetamine Syntheses" (O.Snow) indicates that the PAA --> P2P rxn gives yields as high as 80%. I don't think they are that high. Anyways, IAA is relatively easy to aquire and 'cheap'.

The rxn is also relatively easy and 'fool proof' IMO. This would be 2 simple steps from plant growth hormone to the MDMA of the tryptamine family.

waddayathink ?

--psyloxy--


Rhodium

  • Guest
Re: IAA --> AET
« Reply #1 on: May 18, 2000, 06:56:00 PM »
Yes, it is possible that it could work. As IAA is relatively expensive, one should use a LARGE excess of propionic anhydride (note spelling). But - unfortunately for US bees, propionic anhydride is a watched chemical with a treshold of a few grams (noone asks any questions about it in europe though).

http://rhodium.lycaeum.org


phaidon

  • Guest
Re: IAA --> AET
« Reply #2 on: May 18, 2000, 09:43:00 PM »
Uh, that sounds good! Congrats, psyloxy, wir anderen sind mal wieder blind wie die
Fische rumgelaufen. This is a nice reaction and definately worth trying out, uh,
sorry, dream it out, that is.

Rhodium, you sure Pr Anh is not watched in Europe?

Laters,

-- phaidon, son of apollon

I scorched the Earth, now what do I do tomorrow?

Rhodium

  • Guest
Re: IAA --> AET
« Reply #3 on: May 19, 2000, 02:30:00 AM »
I am very positive. A friend of mine ordered 500ml from aldrich about a year ago, and there were no questions asked, which really impressed him.
The reason it is watched in the US is because of its use in the manufacture of fentanyl derivatives, and I have yet to hear of any clandestine european labs synthing any opioids at all. Its all amphetamines over here.

Nicht vergessen dass die Deutsche sprache hier verboten ist, die Amerikanische Leute können verwirrt werden, ganz als meine Deutsche grammatik.

http://rhodium.lycaeum.org


psyloxy

  • Guest
Re: IAA --> AET
« Reply #4 on: May 19, 2000, 07:10:00 AM »
Hm, I think it wouldn't be that a problem to make propionic anhydride [thanks for your spelling tips] from propionic acid. For IAA: I think I have read somewhere that one could make indole-3-acetaldehyde from tryptophan. Me thinks if one would use a stronger oxidizing agent one would get IAA.

--psyloxy--


obituary

  • Guest
Re: IAA --> AET
« Reply #5 on: May 19, 2000, 07:23:00 AM »
can propionic acid be dehydrated to the anhydride by sulfuric acid?  distilled of as it's formed?


Rhodium

  • Guest
Re: IAA --> AET
« Reply #6 on: May 19, 2000, 06:53:00 PM »
Obi: That won't work.

http://rhodium.lycaeum.org


phaidon

  • Guest
Re: IAA --> AET
« Reply #7 on: June 01, 2000, 12:53:00 AM »
In hindsight, this could provide easy means of production of:

AMT, AET, AMDiPT, and possible 5-MeO subs, e.g. alpha,O-DMS (5-Meo-AMT) etc.
I'll have a look at TiHKAL again, coz' I think there are many unexplored
substitution patterns.

Laters,

-- phaidon, son of apollon

I scorched the Earth, now what do I do tomorrow?

Rhodium

  • Guest
Re: IAA --> AET
« Reply #8 on: June 01, 2000, 02:17:00 AM »
The sodium acetate acts as a base, which catalyzes the reaction. Pyridine can also be used.

You would use acetic anhydride to react with IAA to give 1-indolyl-2-propanone (which could be reductively aminated to AMT). Propionic anhydride to get AET.

What is "reductively alkaminate"? If you mean something like Me2NH + NaBH3CN - yes you would get alpha,N,N-trimethyltryptamine (alpha methyl DMT).

If you start with mexamine, you would need to use HCHO/NaBH3CN to get O,N,N-trimethylserotonin.

http://rhodium.lycaeum.org


phaidon

  • Guest
Re: IAA --> AET
« Reply #9 on: June 01, 2000, 02:27:00 AM »
Rhodium:

alkaminate as in alkyl-amination. Short hand, you got it though.

O,N,N-trimethyl serotonine? Not the objective, I'd say. O yeah, sorry,
I meant starting with 5-MeO-IAA not 5-Meo-T to form a,O-dimethylserotonin.

Why the different proc anyways? (Me2NH compared to HCHO?)

I mean, starting with 5-MeO-T is the formaldehyde / sodium cyanoborohydride
used to introduce methyl groups onto the amine nitrogen?

Does the first one also go for higher alkyls? e.g.

Pr2NH + NaBH3CN to form alpha-Me-N,N-dipropyltryptamine?

What alternatives would there be to the use of NaBH3CN, since it's not
that easy to acquire?

Laters,

-- phaidon, son of apollon

I scorched the Earth, now what do I do tomorrow?

Rhodium

  • Guest
Re: IAA --> AET
« Reply #10 on: June 01, 2000, 03:22:00 AM »
>  I meant starting with 5-MeO-IAA not 5-Meo-T to form a,O-dimethylserotonin.

Yes, would work.

> Why the different proc anyways? (Me2NH compared to HCHO?)

Because if you start with a propanone, you need to add an amine (dimethylamine), if you start with an amine (tryptamine) you need an aldehyde.

> I mean, starting with 5-MeO-T is the formaldehyde / sodium cyanoborohydride
> used to introduce methyl groups onto the amine nitrogen?

Yes. But if you start with 5-MeO-indolylacetone (5-MeO-indolyl-2-propanone), you add dimethylamine.

> Does the first one also go for higher alkyls? e.g.
> Pr2NH + NaBH3CN to form alpha-Me-N,N-dipropyltryptamine?

Yes.

> What alternatives would there be to the use of NaBH3CN, since it's not that easy to acquire?

NaBH4 + acetic acid, NaBH4 + ZnCl2 (to get Zn(BH4)2 ), NaBH4 + Titanium isopropoxide, or perhaps Al/Hg (but I'm not sure if that works on tryptamines)



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