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6-(1H-indol-3-yl)ethanamine

I

ingo_1978

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May 20, 2006
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I was wondering whether moving the side chain to the benzene ring on trypatime could produce some novel drugs when substitued in different places?
 
6-(1H-indol-3-yl)ethanamine are generic "tryptamine"? isn't it?
 
ingo_1978 said:
I was wondering whether moving the side chain to the benzene ring on trypatime could produce some novel drugs when substitued in different places?
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There is an error in your nomenclature. The number in front is the position of attachment of the indole ring to the ethanamine side chain. Thus, tryptamine is 2-(1H-indol-3-yl)ethanamine. What I think you mean is 2-(1H-indol-6-yl)ethanamine. Compounds based on this structure might be stimulants, but I doubt they would be psychedelics, since the indole NH has a specific hydrogen bond formed when tryptamines bind to the 5HT-2a receptor.
 
Come on OP, you are speculating on a positional isomer of tryptamine without having any justification.

Ethanamine only has carbons 1 and 2.
 
^ I don't think he's going to understand what you mean by that.

The way you've named it, it says that the amine is on the 6 carbon of the ethyl. Since ethyl has two carbons it cannot work. I assume you're talking about 1-(1H-indol-3-yl)ethanamine
 
What the heck is so difficult about posting a picture of the structure in question? ISIS resp. SymexDraw are free, add ImageShack, and you're done. This constant confusion and threads which start with several posts who have to deal out what we are actually supposed to discuss about are severly annoying.
 
The OP obviously means this:

ImagesHandler.ashx


Which is 2-(1H-indol-6-yl)ethanamine.

But more importantly: so what? It's not like the brain is gonna be like, "Well the little tail is in the wrong place but I'm sure I can cram it in somewhere."
 
... said:
The OP obviously means this:

ImagesHandler.ashx


Which is 2-(1H-indol-6-yl)ethanamine.

But more importantly: so what? It's not like the brain is gonna be like, "Well the little tail is in the wrong place but I'm sure I can cram it in somewhere."
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That is the chemical I was talking about. I thought it could be the basis of some interesting stimulants or entacogens? or is the nitrogen on the ring going to cause problems?
 
well the other isomer and the sidechain drawn a bit differently looks alot like MDPEA. probably and alpha ethylation would bring something like MDA
 

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Hello, I am a big time lurker. I have pondered this molecule for a long long time. Glad someone else discovered it as well and inspired me post. I've checked the literature a while ago and nothing turned up. This molecule should be something interesting considering 6-APB is active. I'm not quite sure how to post pictures, but i've attached the comparison to mdma. Any additional information would be greatly appreciated
 

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In some old post from f&b (i think) I read that the Oxygens in MDMA cause H Bonding with some receptor residue, NH having an H sticking out..wouldnt that imrpove h bondig propertys even?
 
^Xayo said:
In some old post from f&b (i think) I read that the Oxygens in MDMA cause H Bonding with some receptor residue, NH having an H sticking out..wouldnt that imrpove h bondig propertys even?
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no: indole is aromatic, so the H isn't sticking out and the free electron pair is committed to the pi ring

I think
 
While the lone electron pair takes indeed part in indole's aromaticity, the proton is nonetheless "sticking out" and, thus, is capable of acting as hydrogen bond donor.
 
The methylenedioxy oxygens are H-bond acceptors. I'm pretty sure the NH is a much weaker H-bond acceptor.
 
ingo_1978 said:
That is the chemical I was talking about. I thought it could be the basis of some interesting stimulants or entacogens? or is the nitrogen on the ring going to cause problems?
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The NH is a hydrogen bond donor. That will significantly affect binding, I think. The ether linkages in benzodioxole (MDMA's ring system) are hydrogen bond acceptors, which is quite a bit different from a hydrogen bond donor, y'hear?

You're better off with 1-(1-methyl-1H-indol-6-yl)-propan-2-amine. I'm still not sure: my understanding of the pharmacophore says that a hydrogen bond acceptor meta to the alkylamine (on the benzene ring) is ideal, e.g. 3-methoxy, 3-fluoro, or 3,4-methylenedioxy.
 
atara said:
The NH is a hydrogen bond donor. That will significantly affect binding, I think. The ether linkages in benzodioxole (MDMA's ring system) are hydrogen bond acceptors, which is quite a bit different from a hydrogen bond donor, y'hear?

You're better off with 1-(1-methyl-1H-indol-6-yl)-propan-2-amine. I'm still not sure: my understanding of the pharmacophore says that a hydrogen bond acceptor meta to the alkylamine (on the benzene ring) is ideal, e.g. 3-methoxy, 3-fluoro, or 3,4-methylenedioxy.
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If this is true, why does 5-APB show MDMA like properties? The oxygen in 5-APB is in a benzofuran ring. Oxygens in furan rings are not considered hydrogen bond acceptors to my knowledge.
 
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