Author Topic: 4-hyrdoxyindole  (Read 4281 times)

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  • Guest
« on: March 29, 2002, 06:58:00 PM »
"Interestingly, homolytic attack by *OH on the indole nucleus affords mainly 4-hydroxyindole.

M. Julia and F. Ricalens, Contem. Rend. (C) 275, 613 (1972).   "

Taken from:

 Newkone, George R.  Contemporary heterocyclic chemestry.  John Wiley and Sons, Inc.  1982.  p 76.

So, would indole, exposed to UVs, with catalyic amounts of nitrous acid be enough?  I imagine I'm wrong here, b/c I can't find enough good refs on this, but I feel justified just finding the above-posted reference.  Would it be better to use H2O2 in then presence of some metal? This would form the ion as well, of course.

I don't have access to the original article (*sniffle*), because I'm not as cool as someone out there.  I'm sure it would answer many of my questions . . .

I was tempted to wait to post, until I read more on this, but I'm sure someone out there will enjoy this.

I'm late for class again, *sigh*  ;)

No barbed wire can cage a bee.


  • Guest
« Reply #1 on: March 29, 2002, 07:09:00 PM »
I read the CA article five years ago or something like that, and the product was all the possible hydroxyindoles (although mostly 4-OH). Cheap method though.


  • Guest
Michael Valentine
« Reply #2 on: March 31, 2002, 04:43:00 PM »
Do you know the method exposed in Michael Valentine's Psychedlic Chemistry to convert DMT in psilocin and others ?
0.01 M DMT, 0.02 phosphate buffer pH 7.2 containing 0.5 mM disodium EDTA and 0.01 M ferrous sulphate (may be CuCL works) and add with stirring at 20-22 C 0.02 H2O2 (0.01 M may increase yield) to get 30 % of product containing 4-OH DMT and other OH DMT and must be chromatographed. I wonder if there's something better to convert DMT in psilocin.


  • Guest
Yields suck, MVS too
« Reply #3 on: March 31, 2002, 07:03:00 PM »
Look at the yields from the original paper. They are much lower. It's in no way a practical method.