DEIA (The Acetamide DET) – N,N-diethyl-2-(1H-indol-3-yl)acetamide

[keskoe]

Was recently given a sample of this and haven't been able to find any information regarding it.

The only description given was:

Containing similarities to; Lysergic acid diethyl amide, which is a tryptamine, this tryptamine acetamide; “DEIA” (N,N-dimethyl-indole-3-acetamide) is for study relating to it being a “compact” LSD-like structure, with the; N,N-DIETHYL, the amide & being a tryptamine.

Some have said it might just be a stepping stone to DET (by removing the oxygen), but I doubt I would've been given it if so.
Another mentioned it should have the same activity of 4-subbed psychs. I'm just not sure.
Don't have time to try for a few months, but in time will begin with sub-mg doses and slowly move up.

Any information or help would be appreciated!

I've attached the HNMR-Spectra here

EDIT:
Here's the Pubchem listing: https://pubchem.ncbi.nlm.nih.gov/compound/15043477
and the ChemSpider listing: http://www.chemspider.com/Chemical-Structure.22408384.html

If they help

 

[Neuroborean]

This sound like alien chinese to me
never heard of that molecule.

 

[keskoe]

This sound like alien chinese to me
never heard of that molecule.

Haha, surprisingly not from China. Neither had I, happy it was given to me, but also spooked!

 

[Skorpio]

I would assay up from sub milligram doses, spread apart by a week or two at a time. I would guess it is weaker than LSD by at least an order of magnitude, but I wouldn't gamble on it.

 

[AlsoTapered]

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.6b00276

 

[Cwest]

has anyone tried this?

 

[sekio]

It looks to me like a metabolite. I would assume activity would be low due to lower lipophilicity.

 

[fm3]

It looks to me like a metabolite. I would assume activity would be low due to lower lipophilicity.

This idea of lipophilicity being the main factor in the psychoactivity of a compound in this case ignores the fact that DET’s logP is much higher than any estimate of the optimal value for crossing the blood-brain barrier ( 3.3 > 2.0 ).

If this is less active or inactive, it is more likely to be due to the ease of oxidative deamination.

I’m not sure anyone well-versed in pharmacology would look at the structure here and predict it to be active in the human brain in unchanged form.

 

[sekio]

This idea of lipophilicity being the main factor in the psychoactivity of a compound in this case ignores the fact that DET’s logP is much higher than any estimate of the optimal value for crossing the blood-brain barrier ( 3.3 > 2.0 ).

It's a good rule of thumb that, in general, more lipophilic substances cross much easier than less. But just because the logP is high doesn't mean it makes it impossible to cross. PCP has a LogP of 4.14 and THC has a LogP of 5.53 (Chemdraw estimation) but neither of those has any trouble making it into the BBB. For laughs, JWH-176 is a pure hydrocarbon with LogP 6.91 and is an active cannabinoid. And on the other side of things, caffeine has a LogP of -0.55, and also makes it in the brain, so what do I know.

This DET-amide has a Chemdraw predicted LogP of 1.38, for whatever it's worth, and to my knowledge lacks any known active compounds of comparable structure. So I'm not confident about activity until there is new data, preferably a bioassay.

 

[MsDiz]

It's a good rule of thumb that, in general, more lipophilic substances cross much easier than less. But just because the logP is high doesn't mean it makes it impossible to cross. PCP has a LogP of 4.14 and THC has a LogP of 5.53 (Chemdraw estimation) but neither of those has any trouble making it into the BBB. For laughs, JWH-176 is a pure hydrocarbon with LogP 6.91 and is an active cannabinoid. And on the other side of things, caffeine has a LogP of -0.55, and also makes it in the brain, so what do I know.

This DET-amide has a Chemdraw predicted LogP of 1.38, for whatever it's worth, and to my knowledge lacks any known active compounds of comparable structure. So I'm not confident about activity until there is new data, preferably a bioassay.

Just to say, nice to see you back posting @sekio

 

[HOOH]

It's not a "compact LSD" just because it has the diethylamide moiety...

 

[Bagseed]

It's not a "compact LSD" just because it has the diethylamide moiety...

yeah and it's completely missing the basic tryptamine nitrogen (amine) which both trypts and lysergamides have...

 

[Didgital]

yeah and it's completely missing the basic tryptamine nitrogen (amine) which both trypts and lysergamides have...

Nah it's got both the indole nitrogen and then the ethylamine side chain nitrogen. It doesnt have the amide nitrogen from lysergamides.

I'd be curious if its active. It might act as a prodrug? Just speculating tho.

 

[vecktor]

Bagseed is 100% correct, the structure does not have the basic tryptamine nitrogen, it is an amide and the lone pair is therefore delocalised like in lysergamides.

indoleacetamides are not active at 5ht AFAIK and are not prodrugs to much except plant growth hormones.

A few of these amides have GABA-ergic activity and some bind diazepam mitochondrial binding site and alter steroid metabolism but otherwise are uninteresting

 

[Bagseed]

Nah it's got both the indole nitrogen and then the ethylamine side chain nitrogen. It doesnt have the amide nitrogen from lysergamides.

I'd be curious if its active. It might act as a prodrug? Just speculating tho.

as vecktor said, amine nitrogen is different from amide N regarding the electronic properties, so the binding at the receptor will be different.

 

[AlsoTapered]

Catalytic tryptamine processes and precursors
Publication Number: WO-2022232931-A1
Priority Date: 2021-05-05

Amine synthesis by amide reduction

Reduction to amine looks a total pain. But I am not surprised. Don't forget that some genius had 2,5-dimetoxy-4-bromoaminorex produced as well as 2,5-dimethoxy-4-bromo benzylpiperidine. Likely the same person. Someone with very limited understanding of chemistry OR someone who has found a simple reduction methodology is behind it. IF the same site is offering reducing agents, that's a good clue.

 

[fm3]

I know synthesis discussion is limited to vague terms, but the 2C-B-Aminorex is made in one simple step from beta-hydroxy-2C-B, and that has been ‘on the market’ and is probably hard to sell.

This (OP compound) would be incredibly easy and cheap to produce as well, from Indole-3-acetic-acid (used in MASSIVE quantities as a plant hormone) in two 95% yielding steps at RT with two reagents sold @ cents/KG in industrial quantities.

I’m not sure if that is completely on thread, I mean, whoever is selling this made this compound, not was able to easily reduce this amide to the amine (DET) themselves or is selling it for that purpose in mind.

Barely-active or inactive novel RC analogues are nothing new, right?

 

[AlsoTapered]

Beta hydroxy 2CB. Oh yes - that cheap, common precursor... not. Also the aminorex class has 5HT2b affinity which doesn't make it a good target unless one can firmly (with evidence) demonstrate that ring-substitution removes such activity as, you know, it causes possibly fatal heart-valve damage. Interesting for research purposes, not a reasonable product for many, many reasons.

https://www.tocris.com/pharmacology/5-ht2b-receptors

Run a training-set of 5HT2b ligands... and see what you get.

I'm sure that indole 3 acetic acid IS a possible precursor but if the target isn't active, what is the point? As someone mentioned, it MAY have MAOI activity but it has no known 5HT2a affinity.

I feel pretty sure that between Shulgin, Nichols, Helm and the others that have tested the activity of many thousands of compounds, if something so simple worked, it would be noted. I mean, I did check PubChem and you can too. Every paper, every patent IS there and nobody suggests that it's active. No basic nitrogen.

Serotonin 2A (5-HT2A) Receptor Function: Ligand-Dependent Mechanisms and Pathways - Serotonin Receptors in Neurobiology - NCBI Bookshelf

It has been studied since the 1960s so it isn't that I am claiming to have tested BUT I also didn't need to produce an aminorex derivative believing that ring-substitution could engender 5HT2a activity because I first derived a training-et of KNOWN ligands. We made the p-Me, m-Me and 3,4-MD derivatives (the last being example 13 of the original Poos patent) so balancing monoamine transport activity has been worked out and indeed Nichols HAS the worl.

I know rational design is a little old fashioned these days, but it's worth finding the affinity/activity of 30 or 40 ligands and to perform 3D QSAR data. OK it may take a few weeks to find the data and maybe 24 hours for the software to run, but you do find that it's surprisingly efficient at recognizing key moieties and their relative spatial positions and orientations.

In the case of PEAs and tryptamines, that basic nitrogen, or rather the N: is key... I mean it's present in every one of the lysergamides, tryptamines, PEAs and so on. But of course, one has to consider that antagonists also have by the very name significant affinity. So including them in a training set is perfectly valid:

https://www.tocris.com/pharmacology/5-ht2a-receptors/antagonists?gclid=CjwKCAjwscGjBhAXEiwAswQqNLFyAB87FJksXYZHT3ozODypVl6Wjk8e0SDflhoezrzGZrF8KgXTUhoCc_oQAvD_BwE&gclsrc=aw.ds

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So no excuses, run a training set.


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And again, run a training set.

It's boring and it's time consuming BUT it's free to do:

I have gone to the trouble of finding everything for you,

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5418185/

Right down to free online software to do just that. Yes it's boring, yes it's time consuming and yes, it isn't perfect, but when one also applies the Ro5 and rational metabolic analysis, one can identify compounds pretty well before researching at least 2 facile syntheses along with costings of both - often the longer routes work out cheaper, especially when one includes solvent management.

 

[Cwest]

anyone try this? inactive?

 

[AlsoTapered]

Many plants have tried it. It's a fine precursor to DET but isn't active.