Hive Tryptamine Chemistry

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	Tryptamine Chemistry

All 6 posts Subject: DMT from Imitrex (Sumatriptan) Please login to post Down

peanutbutter
(Stranger)
11-28-03 06:12
No 473570
      DMT from Imitrex (Sumatriptan)

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

Riding the waves of the great electron sea....

moldie
(Newbee)
11-28-03 07:34
No 473578
      I was researching possible routes to DMT ...

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
(Stranger)
11-28-03 11:58
No 473621
      Good Idea

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

peanutbutter
(Stranger)
11-29-03 15:16
No 473771
      What part of the chain

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
(Stranger)
12-02-03 01:19
No 474187
      Desulfonation

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
(Moderator)
12-02-03 08:47
No 474239
User Picture       You can oxidise the methyl group to the ...

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.

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	All 6 posts		Subject: DMT from Imitrex (Sumatriptan)		Please login to post		Down


		peanutbutter (Stranger) 11-28-03 06:12 No 473570				DMT from Imitrex (Sumatriptan)
						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 Riding the waves of the great electron sea....



		moldie (Newbee) 11-28-03 07:34 No 473578				I was researching possible routes to DMT ...
						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 (Stranger) 11-28-03 11:58 No 473621				Good Idea
						It is true tha Imitrex is quite expensive but it is also easily obtainable and 100% under the radar.



		peanutbutter (Stranger) 11-29-03 15:16 No 473771				What part of the chain
						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 (Stranger) 12-02-03 01:19 No 474187				Desulfonation
						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 (Moderator) 12-02-03 08:47 No 474239				You can oxidise the methyl group to the ...
						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.

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