5OH-DMT -> 5MEO-DMT?

[Kid_Orgo]

Since I am only in my first semester of college organic chemistry, this question may be completely ignorant. If it is, please delete this post, and I'll refrain from posting anything else until I'm more certain of my material.

I've read that bufotenine has severe body effects and is only a mild entheogen. Since bufotenine is extractible from A. columbrina, which is commercially availiable on the web (Iamshaman.com, for one), I've been thinking about ways to convert it into something more useful. 5Meo-DMT springs to mind.

I've used the search engine, and the only relevant posts have been sytheses from the ground up. I found one post by lego which contains the phrase:

The methylation of a 5-substituted tryptamine to a 5-substituted DMT with HCHO (formaldehyde) and NaBH4 (sodium borhydride)

Essentially, I'd want to replace that H on the 5-OH with a methyl group, correct? Is what I'm getting at even possible?

[Bandil]

1: By using formaldehyde and borohydride you methylate the amine group, and bufotenine is allready fully N-methylated, so nothing will happen

2: No, you do not want to replace the -OH group with a methyl group. You want to make an ether of it, which is done by using a methylating agent like dimethylsulfate, trimethylphosphate or dimethylcarbonate. I'm not sure though, if any parts of the indole nucleus will be methylated aswell...

I'm no sure the route is to viable if you are going to extract the goodies from a plant source, as you need a lot to be able to process it further...

Regards
Bandil

[Lilienthal]

From what I read in articles from Jonathan Ott in the Journal of Psychoactive Drugs the weak activity and predominant side-effects caused by bufotenine seemed to be a misconception.

There is a way to selectively alkylate the OH group. Simply deprotonate it to make it a stronger nucleophile than the competing tertiary amine. But don't use a too strong base so that the indole-NH will not be deprotonated.