Seeking a chemical understanding of Tryptamine potency

I wonder if it has anything to do with the carbon groups on the non-indolyl nitrogen.

This is tryptamine, the basic:



Notice that there is only one Carbon bonded to the upper nitrogen.

In DMT, there are two methyl (CH3) groups there. That is the only different between the molecules. In DPT, there are two propyl groups (3 carbons, seven hydrogen)

The only difference between DMT and psilocin is the presence of an -OH group.



I wonder if the presence of the hydroxyl group introduces steric strain that would account for the decreased affinity. The OH would also make it more (or perhaps) less reactive in certain situations, but I don't know enough to infer anything from that.

And if you look at LSD, it's a different story all together.


It has TWO indolyl groups (the hexagon and pentagon sharing a side, with the 5 member ring having a nitrogen), two ethyls (CH2CH3) coming off the other nitrogen , and some functional group I don't know anything about (Carbon doubly bound to oxygen, and singly bound to another carbon and a nitrogen). LSD is ridiculously more potent than the others.

EDIT:I think I'm wrong about there being two indole groups. I don't know what that second thing is.

You guys have any ideas about this? Come on orison, I can't tell if you're a chemist pretending to be a crackhead on line for shits and giggles or the other way around.

Just for funsies, let's look at serotonin.



Intresting. It is similar to psilocin in that it bears the -OH group, but the second nitrogen is only bonded to two hydrogens. I'm at a loss here.

 

I wish I could understand this better, but what is the point you are trying to make?

 

The attempt is to coordinate the experience with the geometry

 

the first half makes sense to me.
it seems that the potency could come from the groups of the non-indole nitrogen. but di-methyl and di-propyl are both pretty potent. i guess DPT is less potent since it requires more material? maybe serotonin is present at very low levels in the brain, so it is actually the most potent? but i'm just talking out of my ass now, and that's probably not true, b/c the tryptamines need to have higher affinity for the receptor than serotonin...

it's too bad that Di Ethyl Tryptamine isn't better characterized. where does it's potency lie? that could help answer your questions, and i don't think it goes farther than propyl does it?

the OH group idea of yours seems good to. maybe that group causes reduced affinity, or maybe it gets removed to become more structurally like DMT?

good post

 

it seems that DET is more potent than DPT, but not quite as potent as DMT.

go figure..but i've only tried the second 2.

c'mon pork, you're a freeken biochemist aren't you? you have tihkal? ...get a move on!

 

i dont know what all that means. might help out though..

 

so that does make it seem like a longer carbon chain decreases potency. but serotonin's still a mystery.

i was just gonna say i have to open up TiHKAL. it's still in the plastic wrap though, as i'm currently reading PiHKAL. and with all the science i should be reading for school, it might take me awhile.

and yes, i'm a biochemist. but that's a pretty big umbrella term, in a way. i'm a biochemist that works with the single celled eucaryote, Saccharomyces cerevisiae, or budding yeast. and i work on tRNA and translation...not so much brain chemistry when you're model organism doesn't have a brain
i did take neurobiology back in undergrad. i had a big hunch that my prof. there had experimented with LSD back in the day. i wasn't experimenting with RCs when i took that class, just L and mushrooms.

 

i know you're much more into bio...and i read pihkal first, as at the time i'd NEVER taken any PEA's [aside from amphetamine] and it was completely uncharted territory.

 

in serotonin the OH group is in a different place to. In psilocin, it's only one carbon away from the bridge that joins the two rings. In serotonin, it's two carbons away. i dunno, at this point I've pretty much exhausted my knowledge of chemistry (at least for the time being).

 

^^^i didn't notice that at first glance. good point