Phenethylamines 2,4-dimethoxyamphetamine - some short info

[ralf2]

Hi all,
I usually don't like disclosing effects of obscure drugs in case some asshole starts to sell it and make it illegal. But in this case I hope this drug is not potent enough to sell.

Maybe you have read the entry for 2,4-DMA in PIHKAL. It's only tested up to 60mg with some inconclusive results.

I have tried it at higher doses and thought I would share the results for science.

At 100 and 150mg you get this weird feeling that is hard to categorize, for sure it is trippy but hard to put your finger on it. Like taking a small step away from reality.
But at 200mg you can recognize that it is like a classic psychedelic. Closing my eyes I could see faint geometric patterns. But the mind trip is stronger than the visuals. Somehow it reminded me of a lower dose of DOM. In that you are tripping for sure, but not so much visuals.
Half way through the trip my partner came over unexpectedly. It was nice to have her with me and it wasn't that hard to act normal. Sex was nice even though it was a bit difficult to get hard.

I took it at around 16:30 and by the time I went to bed at 23-00 something it was into afterglow territory. But it was still a bit tricky to get to sleep, but it was possible eventually.

Overall I think it is pretty nice. Especially at the lower doses I liked just taking a bicycle ride around the neighborhood in the summer evening. I don't have any more now, but it would have been interesting to see how it develops at higher doses.

I think this must be one of the simplest psychedelic molecules which is interesting to me.

 

[xdrc]

Thanks for your service! How is the bodyload, anything to be weary of?

 

[Allylbenzene]

Very cool.

I hope this drug is not potent enough to sell

I think in some ways potency is overrated. It's ideal for research purposes but shouldn't serve as a "benchmark" for therapeutic/recreational drug design.

I think the image below gives some (2D) context for what you reported; comparing DOM and 5-desmethoxy-DOM to tryptamines with 5-HT2A activity.

Top row:
• 5-MeO-DMT / 7-Me-5-MeO-DMT / 7-Me-αMT
Bottom row:
• DOM / 5-desmethoxy-DOM

I think this must be one of the simplest psychedelic molecules which is interesting to me.

If someone made the α-ethyl of 2,4-DMA that could be interesting. Likewise the α-ethyl of TMA-2 aka 4C-O.

 

[xdrc]

Your structures are wrong Allylbenzene, 2,4-DMA is the 2,4-dimethoxy compound, i.e. methoxy not methyl in the para position.

 

[Allylbenzene]

Thanks, the labels were incorrect...fixed.

Considering the SAR of '4 PEA correlating to '7 indole (thus OPs 2,4-DMA correlates to 7-MeO-T), I found this 2014 paper for 7-MeO-tryptamine which may give relevant SAR insights:

Alpha-ethyltryptamines as dual dopamine-serotonin releasers

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential.

— https://doi.org/10.1016/j.bmcl.2014.07.062

 

[ralf2]

Thanks for your service! How is the bodyload, anything to be weary of?

I don't remember any special body load, and didn't put anything into my notes (it was a few months ago now). At least I wasn't nauseous. So I don't think there was anything spectacular at least.

I think in some ways potency is overrated. It's ideal for research purposes but shouldn't serve as a "benchmark" for therapeutic/recreational drug design.

Yeah, agreed. For a normal user it shouldn't matter if you take 2mg or 200mg. I just meant that the profit margin should be lower for someone trying to sell it, if a dose is much higher than other substances. Which might cause vendors to skip it hopefully.

 

[Allylbenzene]

I think in some ways potency is overrated. It's ideal for research purposes but shouldn't serve as a "benchmark" for therapeutic/recreational drug design.

Yeah, agreed. For a normal user it shouldn't matter if you take 2mg or 200mg. I just meant that the profit margin should be lower for someone trying to sell it, if a dose is much higher than other substances. Which might cause vendors to skip it hopefully.

I agree, I was specifically referring to the general attitude of recreational users who prioritise potency. Often potency implies selectivity and results aren't necessarily ideal (eg NBOMe class), but exceptions like LSD demonstrate why polypharmacology is key.

 

[Didgital]

Yeah, agreed. For a normal user it shouldn't matter if you take 2mg or 200mg. I just meant that the profit margin should be lower for someone trying to sell it, if a dose is much higher than other substances. Which might cause vendors to skip it hopefully.

I wouldn't worry. You are not the first person to test this or to wonder about these compounds. About a decade ago, I stumbled across a direct report from a polish chemist who synthesized both 3,4-DMA and 4-OH-3-Meo-amphetamine from methyl eugenol and eugenol respectively. His report was similar in that both compounds were psychoactive, but vague in description, not unpleasant, but not the MDA/MDMA substitute he was hoping to find. I do remember him mentioning some body load (clenching) for one of the compounds (which one I can't remember).

It was a unique little write up akin to shulgin writeups, and sadly I have not been able to find it for many years.

Anyway, thank you for your report. BL is one of the few places we can read such things on novel compounds, that's why I've been here for ages. I don't think I would be here if we continually discussed the same very well known compounds over and over and over and over.

 

[Allylbenzene]

From

https://doi.org/10.1021/jm00152a005

5-HT1 and 5-HT2 binding characteristics of [DOB] analogs

DOB...binds selectively to central 5-HT2 binding sites. Systematic removal of any or all of the aromatic substituents had relatively little effect on 5-HT1 binding but reduced 5-HT2 binding by approximately 2 or more orders of magnitude. Demethylation of the 2-methoxy group of 1a, or introduction of an N-n-propyl group, doubled 5-HT1-site affinity but decreased 5-HT2-site affinity by 3- and 30-fold, respectively.

Looking at item #9 (2-MeO-4-Br amphetamine) the change in 5-HT1 & HT2 potency (compared to DOB) may be relevant to your 200mg 2,4-DMA experience. 5-HT1 activation appears to play an important role in the "resolution" of psychedelic effects, meaning 5-HT1A agonism allows for "higher resolution" (due to less serotonergic "noise").

The usual role [of HT1A] is one of feedback inhibition. A great many 5-HT1A receptors in the brain are presynaptic autoreceptors which essentially tell transmitting neurons when it's time to stop releasing serotonin.

Speaking generally here, I think viewing 5-HT1A as acting in opposition to 5-HT2A detracts from the more nuanced dynamics occurring.

Somehow [2,4-DMA] reminded me of a lower dose of DOM.

Interestingly #9 (2-MeO-4-Br amphetamine) generalised to DOM in one of the discrimination tests.

The 2-methoxy-4-bromo derivative 9 produced only partial generalization (65% DOM-appropriate responding at 12 mg/kg) ... interestingly, the one animal that did respond made greater than 90% of its responses on the DOM-appropriate lever.

 

[Didgital]

Why is ignored member posting information that has nothing to do with 3,4-DMA??? It just clutters an otherwise very interesting thread.

None of his comments/diagrams mention 3,4-DMA anywhere at all...

At least the last diagram is concerning phenethylamines, which is at least in the same family... gj I guess..

 

[Allylbenzene]

Why is ignored member posting information that has nothing to do with 3,4-DMA??? It just clutters an otherwise very interesting thread.

OP posted about 2,4-DMA, not 3,4.
Perhaps you misread?

None of his comments/diagrams mention 3,4-DMA anywhere at all...

They actually have SAR relevance to OPs compound, seems you misread.
If you contact Jason Wallach he'll clue you into why the 2,4- pattern is relevant. His compound 4-bromo-2-methoxy PEA shares key features with OPs 2,4-DMA.

At least the last diagram is concerning phenethylamines, which is at least in the same family... gj I guess..

I'm sure if you ask around someone will kindly explain the relevance of tryptamines to PEA SAR.

 

[Didgital]

OP posted about 2,4-DMA, not 3,4.
Perhaps you misread?


They actually have SAR relevance to OPs compound, seems you misread.
If you contact Jason Wallach he'll clue you into why the 2,4- pattern is relevant. His compound 4-bromo-2-methoxy PEA shares key features with OPs 2,4-DMA.


I'm sure if you ask around someone will kindly explain the relevance of tryptamines to PEA SAR.

Ah you are right I totally misread the title initially the other day.
My bad. I was wrong.
Saying that isn't difficult.

I still don't see a single 4-meo substitution on the last diagram and the yellow highlighted lines don't have anything in common with 2,4-DMA.
Tryptamine to PEA SAR different enough one really shouldn't extrapolate from one to the other. Otherwise 5,6-MDO tryptamines would probably be interesting.

 

[Allylbenzene]

I still don't see a single 4-meo substitution on the last diagram and the yellow highlighted lines don't have anything in common with 2,4-DMA.

You don't understand context?

Otherwise 5,6-MDO tryptamines would probably be interesting.

5,6-MDO-T doesn't overlay properly. There are nuances in the T/PEA SAR which must be considered. If you note how fenfluramine overlays αMT's pyrrole or how 3,4-MMA overlays 7-methyl-DMT, you might see why 5,6-MDO isn't workable.

Tryptamine to PEA SAR different enough one really shouldn't extrapolate from one to the other.

Go tell that to 4DQSAR, he'd teach you a few things.