I've been looking at the Tryptophan -> Tryptamine methods
in Rhodium.  I'm wondering, would it be possible to use the same methods to convert 5-HO-Tryptophan -> 5-HO-Tryptamine (seretonin)?  Seems to me this would be a deliciously easy method of making 5-MeO-DMT, by reacting it with MeI.

Also, would it be possible to put different groups on the O and N? Say for making 5-MeO-DIpT?  Or could we remove the hydroxyl, and have plain tryptamine for making dialkyl tryptamines?

I'd go look some of this stuff up, but it's Labor Day weekend and the library's closed. They even shut down their online catalog! Anyway, if you could point me to some good papers in this area, I'd be quite satisfied.

Would it? It would be a normal SN2 reaction in both cases.

Of course I don't know how the conjugated indole system would affect nucleophilicity, and there would be problems with quaternization of the nitrogen, but I don't see any glaring reason this isn't practical.

Hell yeah it would dimethylate, you'd get a mix of 4 or 5 different products, it would be quite a hassle.

You could acyalate the amine group first then treat w/ Methyl Iodide. Then you'd have melotonin... Melotonin's acytal group should be cleaveable with LiAlH4, giving N-methyl 5Meo tryptamine. This interesting compound could be further reacted with Either Alkyl Halides and a base like Triethyl amine (No Methyl iodide cuz the product would quaternize . It should be noted that this route to A whole new world of undiscovered 5Meo N-methyl tryptamine analogs. Methyl propole, or isoprople analogs should make for an interesting product.....  Hell the sky's the limit!