"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*  

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No barbed wire can cage a bee.

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.

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.

Look at the yields from the original paper. They are much lower. It's in no way a practical method.