DMT from tryptophan?

A possible route via decarboxylation and n-methylation via carbamates

Category:

Science & Technology

Tags:

• chemistry

[Fomelogo]

you had me at DMT...

also, i have a quick question: I have a Grignard reagent, a vinylmagnesium bromide, which has been on anhydrous THF for quite a while. It's MERCK Grignard and I made it react with an aldehide (3-formyl indole) but it was screwed up and i was wondering if you knew

what could happen to a grignard reagent over time, such as this one?

again, thank you very much for your channel, please keep it up. Everyone in my faculty is watching this

[Fenderson5555]

@Fomelogo Grignard reagents aren't fantastically stable to keep sitting around, it might just have gone off/hydrolysed/whatever, depending on how well it was sealed. Although, if you only reacted with one equivalent, it might have just deprotonated at the nitrogen instead...

[Fomelogo]

@Fenderson5555 I'm pretty sure the grignard was properly sealed, as it was MERCK bottle with a rubber on the top, so the only way in was with a needle. The 3-formyl indole was protected, previously, with a 4-fluorbenzenesulfonyl group.

Someone told me, and i said to myself "I will ask Fenderson5555, he probably knows the answer", that the Vinylmagnesium Bromide can polimerize upon itself... Is it possible??

By the way, how do you make these videos? i find them extremely useful and nice!

THANKS

[Fenderson5555]

@Fomelogo ah, in that case, I'm sorry to disappoint you, but I've got no *specific* experience with these kinds of Grignard reagents going wrong. Nothing immediately springs to mind. As for how I make the videos, I use CamStudio to record drawings made in OneNote, and then edit the whole thing together with VirtualDub. It seems to work well enough.

[Rannyfash]

cool, if a quarternary methyltryptamine salt was made, is it possible to remove one single methyl group, it would seem easier in terms of number of steps, would it decompose easier than dmt

[atomicwave]

wut?

[DrDoak1000]

What would be the appropriate solvent for these reactions? I would assume ether but I haven't learned much about solvents yet. Also is every step a 1:1 molar ratio except for the final reduction?

[raysday4321]

Holly Skittles ~

[TheBubaSqua]

Could you use the Barton decarboxylation to decarboxylate the tryptophan?

[lamahska]

was going through a couple of your videos, sir, and I am blown away by your knowledge!! I am starting grad studies this August for a PhD in immunology (I know, different field!), but jesus christ, I can only wonder if one day I can amass this much knowledge in my field too!

[WhoAteMyCheezIt]

could you decarboxliate tryptophan and then react the compound with NaNO2 and HCl in dimethyl amine. Forming a Diazonium salt that will react with the dimethyl amine to form DMT?

[Fomelogo]

@Fenderson5555 Well it works perfectly nice, and thank you very much for the answer. I will keep in touch with you if i ever have an answer...

thank you!