DMT from Imitrex (Sumatriptan)

[peanutbutter]

Sumatriptan is a sulfonated tryptamine NEARLY analagous in form to DMT.  Has anyone ever come across a proposed mechanism for the reduction of sumatriptan to DMT?  After all, sumatriptan contains DMT in full form!  A DESULFONATION AND A DEMETHYLATION WOULD MOST LIKELY DO THE TRICK. Does anyone have any further references or ideas?  Check out the sumatriptan link:

http://us.gsk.com/products/assets/us_imitrex_nasal_spray.pdf

 -PB

[moldie]

I was researching possible routes to DMT earlier, and sumatriptan didn't come up, thanks for the idea. Being dmt with a methanesulfonamide in the 5-position, one might be able to use a raney catalyst. Tryptamine is probably a better starting chemical though, mainly because it is cheaper.

[peanutbutter]

It is true tha Imitrex is quite expensive but it is also easily obtainable and 100% under the radar.

[peanutbutter]

What part of the methanesulonamide chain would act as the leaving group?  Could the entire chain be cleaved in one reaction? 

Pricewise, you can get about 1 gram of sumatriptan accompanied by the succinate salt for whatever the cost of your copay is (assuming that you have prescription insurance)in the 100mg Imitrex tablets.  If you've got a good doctor you could probably get plenty of samples for free!  Here's another link to the structure of sumatriptan:

http://www.ajdesign.com/Elliott/Migran.htm

[peanutbutter]

Well, to answer my own question regarding the leaving group, using a Raney catalyst would cleave the methansulfonamide chain at the sulfur atom.  Thus, one would be left with a methyl group at the 5 position of the benzene ring.  Does anyone know how you could reduce this methyl group?  Please, be careful when working with Raney Catlaysts.  For those who don't know, Raney catalysts are a Ni/Al complex.  They are commercially available in solution.  NEVER let the catalyst dry out!  If the Raney catalyst dries out it will react violently with O2 in the air (boom).

-PB

[Lilienthal]

You can oxidise the methyl group to the carbonic acid (-COOH) and decarboxylate. But that's a multi-step-low-yields reaction scheme. It's WAY easier and cheaper to synthesize tryptamines using the common routes.