Question About Substituted Tryptamines?

[MindWeather]

I have little knowledge of organic chemistry and I just finished reading PiHKAL. I then ran through the list in TiHKAL and I have a quick question about Tryptamines.

Why are there no substituted Tryptamines with chemicals such as Bromine, Iodine, etc?

I noticed on Wikipedia (I am a master of research) that a Tryptamine doesn't have a 2nd or 3rd position, but it has a 4th and 5th (I don't really understand what that means either)?

So, why is it that there is no...say...4,5-bromo-4-dimethoxytryptamine? Maybe you can explain this in some relatively simple way. It would be appreciated.

 

[sekio]

5-Bromo-DMT is a known compound, as is 6-F-DMT. 1-Bromo-LSD is also known, I think, but it has no psychiatric effects.

Compounds like bromine, iodine etc are a lot more prevalent in e.g. radioimaging tracers. Iodomelatonin is one example.

 

[Indole]

It seems like you are trying to compare tryptamine chemistry and pharmacology to that of phenethylamines. There are no tryptamines analogous to the 2C-X's as you seem to be implying. 4,5-bromo-4-dimethoxytryptamine doesn't really make sense, and tryptamines have different pharmacology profiles and SARs from phenethylamines.

If you want to understand organic naming and structures, I suggest reading an introductory organic chemistry book.

 

[ebola?]

Briefly, a lot of these possible SARs remain unexplored because many researchers have stuck closely to Shulgin, Nichols, etc. choices of substituents to explore. A cursory search suggests that ring halogenation at 4, 5, or 6 can yield compounds likely to have activity similar to dmt or psilocin (the case seems similar with methyl substitution, but with increased likelihood of mao inhibition or activity at monoamine transporters). It seems that these ring substitutions coupled with extension of the alpha-chain could confer dangerous mao inhibition (particularly dangerous when coupled with monoamine release or reuptake inhibition, not uncommon with tryptamines, particularly those alpha-chain extended).

SO, I'd tread with caution (if at all) tasting any of these, beginning with compounds for which we have data on binding affinities, monoamine release or reuptake, and a confirmed lack of mao inhibition, of course beginning with Shulgin-titration style micro-dosing.

ebola

 

[MindWeather]

Thank you for clarifying. Question was answered thoroughly. %)