Halogenated Tryptamines?

[Psiloman]

Well,first of al let me say that this is my first post to the hive.I have basic chemistry knowledge but nothing too advanced (in other words ,i cannot perform complex synthesis nor i have a lab)  

My question is pretty straightforward.Are there any halogenated tryptamines and what is known about them and their effects? It strikes me as weird seeing so much alkyl "playing around" in the tryptamine world (TiHkal for example) and no halogenated compounds.For PEAs  halogen substitution has given some amazing results (2c-b ,2c-I) ,why not try it on a tryptamine as well?

I used the search engine but i could not find anything on that,except tryptamines used in radiolabbeling.

Sidequestion:Why is there such an aboundancy of PEAS and not so many tryptamines? (Compare the number of PEAs presented in Pihkal and the number of tryptamines in Tihkal).Is it because the indole ring has less places for substitution.

Sorry if my questions were "naive" but believe me,i did a lot of research to no avail.

With Honour,
Psiloman

[Rhodium]

Why is there such an aboundancy of PEAS and not so many tryptamines?

Because the chemistry required for synthesizing phenethylamines is much easier than that of tryptamines, both in regards to the skill required as well as the number of methods available for performing a certain chemical transformation.

It's also a question of economy, the starting materials required for the syntheses of many common tryptamines can easily cost between 10-100 times as much as the ones used for the most common phenethylamines - A quick look through the Acros catalog gives the following prices:

4-Hydroxyindole (for psilocin, etc): €118/1g
5-Methoxyindole (for 5-MeO-DMT, etc): €65/5g
4-Methoxyindole (for 4-MeO-DMT, etc): €91/500mg
Tryptamine (for DMT, DET, DIPT, etc): €44/50g
Indole-3-acetic acid (as above): €43/25g
Tryptophol (as above): €37/5g
Indole (as above): €35/100g

€1.00 = $1.15

[yellium]

Also, in the tryptamine world you have so many more possibilities to explore - the indole-4 and 5-position, the indole-2 position, the indole nitrogens; whereas for phenethylamines, you're basically 'stuck' with the 4-position, for which it also is far more easier to create synths for (hence the price difference between tryptamine and phenethylamine precursors). Since it is so much work to evaluate all those synths, you can expect to see only the ground scratched for the tryptamines, and the phenethylamines being quite well-researched.

[pHarmacist]

It will bee compleatly impossible for DEA to watch tryptamnines - it's even redicilous that they are making effort. Seamingly endless variation of structures with tryptamine backbone can alter the mind. The only way would bee to make science and thinking itself illegal - that too is of course impossible...

Human Law vs. Nature's law, who do you think wins?

[Lilienthal]

IMHO only 5,7 and 4,7-disubstitutions are interesting in tryptamines in terms of potency, (e.g. 5-Meo-7-Me tryptamines). And of course there are a lot of sidechain variations (e.g. pyrrolidin-2-yl-methyl-indoles) and all combinations of one to four carbon N-substituents (including unsaturated ones). But as Rhodi said, indole and tryptamine syntheses are longer and more tricky compared to phenylethylamines.

[Psiloman]

Thank you people,all of you for dispelling my pressumption that tryptamine substitutions are limited in number compared to PEAs.And also thank you for pointing oyt the economics factor,money expenditures can certainly be a hinderance when researching new compounds!

I wish such research was legitimate (dont we all wish that?) ,and we could someday see a nice synth for something like 5-I-DMT or 4-Br-Dipt...

BTW very nice webpage rhodium,i have started some extensive studying on the material you present in it.GOsh,it could form an encyclopedia!