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 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.

Somehow it [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?

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

If you read 4DQSAR's posts you'll learn why extrapolation is valid.

 

[Didgital]

Now I remember why I have the user set on ignore. Gives vague and often wrong responses without ever directly answering the question all the while being condescending af.

@4DQSAR maybe you can come in and educate us/me about how allylbenzene's comments are relevant? I wouldn't mind hearing from someone who actually knows a little bit about what they're talking about.

 

[Allylbenzene]

4DQSAR maybe you can come in and educate us/me about how allylbenzene's comments are relevant? I wouldn't mind hearing from someone who actually knows a little bit about what they're talking about.

His perspective on SAR is always welcome.
As I wrote in the ULDN thread, even though we're mutually set to ignore - he's an alright guy.

Now I remember why I have the user set on ignore. Gives vague and often wrong responses without ever directly answering the question all the while being condescending af.

You get special treatment.
The 2 statements in my previous post were specially for you. The 1st incited you to learn about SAR; the 2nd to read 4DQSAR's posts about SAR of 7-methyl indoles, 2Cx and the FLY series.

 

[Allylbenzene]

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

Funnily enough the CEO of Tactogen told me he extrapolates PEA/indole SAR, he works professionally developing MDMA-like compounds. Perhaps you're very well educated in chemistry but not SAR?

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

5,6-MDO indoles don't quite work for various reasons, but Nichols mentions this in his patent WO2024091523. It's not an indole but it's fairly close. I don't expect you to appreciate the SAR here.

In some embodiments, exemplary compounds of Formula (5-1B) include:​

well as pharmaceutically acceptable salts, hydrates, solvates, and isotopic derivatives thereof.​

...​

 

[Didgital]

Allylbenzene I'm just going to take you off ignore because you're just going to follow me around and comment anytime I post in PD or MAED That way I can make a post and I won't see and have to click the "see ignored content" button that pops up 30 minutes after I make a comment in PD or MD forums. I can comment directly and you can respond in kind

You talk to Matt? Tregar talks to Matt too. Must be yet another coincidence
one
That's interesting though, I'll have to ask Matt the next time I see him about how he extrapolates PEA SAR to tryptamine among other things. I mean sure they both have a phenyl ring and and ethylamine chain, but tryptamines have 3 carbons between the 1carbon of PEA while PEA's have two. We all hopefully know that extending/shortening a carbon chain by even one carbon CAN produce DRASTICALLY different pharmacology as we see with HOMO-MDxx, MDM1EaA even the the 2C tweetios. 6-me-amt which you highlited seems a bit of a stretch to compare first when there's dozens of other compounds that are structurally much more similar. At least the compounds you (I assume) pulled from Nichol's patent, have 2 carbons instead of 3 between PEA's C1 and the amine. Even though they are ring constrained they at least SHARE the phenethylamine core. I am confused why you included compound #34 as it doesn't even have a substitution at the 2 carbon of PEA's and has a strange methylethanoxy substitution at the 5 carbon of PEA which tbh, I don't think I've ever seen in a known active phenethylamine???? What is your point for including that structure or the other indanyl-1-methanamines? I'm genuinely curious why you're proposing them here unless you are using them to prove that Nichol's extrapolates tryptamines to phenethylamines? Because I would say while they sort of resemble an indole, they are a ring constrained phenethylamine first. I will admit there is some sort of wiggle room regarding comparing tryptamines with phenethylamines when you get strange hybrids like Matt has been develping with Tactogen. That's why I initially reached out to him years ago, as he's exploring some truly novel SAR. But I don't think he's extrapolating I think he's fucking with the pentyl ring in very diverse ways just to explore things that are very different. I don't think he would say he's extrapolating but I will ask him personally. He's always been very enthusiastic to talk to me about a lot of his compounds because most people have no idea about their existence or their potential. BTW, I never claimed to be an expert on SAR, but my understanding is enough that I could probably predict compounds that are active that have never been explored. This thread wasn't even supposed to be about SAR as it was a direct report on the experience of taking 2,4-DMA but like always you had to insert conjecture instead of discuss the actual topic at hand.

I would love to hear more about 2,4-DMA as we have a chance to hear from someone whos tasted instead the compound instead of speculate incessantly. I truly wouldn't know what exactly to expect from 2,4-DMA but I would probably expect it to be more like TMA-6 before making wild assumptions/speculations about weird ass compounds that don't share a simple core structure. I'd love to hear from @ralf2 and ask if he's tried TMA-6 and could make a direct comparison. I've tried TMA-6. I didn't really care for it though it was interesting to explore a different phenethylamine substitution pattern, just like I would be curious about trying a 2,4 disubstituted compounds.

------

If I have to deal with you being a condescending stalker forever, it was SO WORTH it to have "Tregar" self delete his own thread. I think about all the people that WON'T buy his book and WON'T waste their precious time/money supporting a fraud conman who thinks "he's" a chemist when "he's" likely delusional from decades of steroid use. I think about all the people that WON'T end up getting sick like one of the only 2 real amazon reviewers has reported. I only mention that fact because pretty much the exact moment "he" deleted "his" own thread, was about the same time your animosity towards me went into hyperdrive.

It really makes me wonder why YOU care so much about it while the only mention I got from "Tregar" was from "him" trying to sell me HBWR seeds. It's hilarious that "he" deleted that message and replaced it with "Stop harassing my wife" even though that message was dated before @LissieJedi ever even had an account on BL
I personally didn't want the thread deleted. I wanted it LOCKED so that people could read the entire thing and make up their own mind about it but "Tregar" must have really wanted people to not see it for some reason to delete "his" own thread
Maybe "he" finally accepted the fact that it was blatant disregard for BULA and decided to respect the rules that we ALL agreed to in order to use the forum. Somehow I doubt it based on "his" activity in the LSA thread.

As I offered before, I would LOVE to do some sort of facetime chat with you someday (which you declined). We don't even need "Tregar" to be present like I originally requested. I'd love to just talk to you.

Also you have mutally ignored according to your comment in "What's wrong with MDMA" yet you seem to always quickly respond to my comments indirectly for example you said

"If you saw his apparently serious posts in this thread you may be surprised; the comedy writes itself." -- where you even link to this thread where I immediately admitted that I misread and started talking about 3,4-DMA.

Really classy and not petty at all of you.

 

[xdrc]

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.

As this thread is a bit derailed anyways (yet I'd still like to hear some comparisons to other known and similar compounds to 2,4-dimethoxyamphetamine) - I have limited experience with 4-propoxy-3-methoxyamphetamine (POMA), which was probably first made by Hyperlab user "Demonic" (this report may be found on isomerdesign but in PiHKALesque manner features the synthesis which is of course against BLUA). The dosage range given by Demonic is correct but I found nothing worthwhile about the compound. It just made me a little bit confused but never went anywhere, but felt pretty much harmless. No intensification of effects from 150 - 250 mg which makes me think the compound hit its ceiling. I intend to explore the isopropoxy compound and some derivatives as well as MEM and MiPM soon-ish.

TMA-2 which too is an analogue of 2,4-DMA was very interesting to me, albeit plagued with (psychosomatic) bodyload.

Without venturing too much into synthesis talk, 2,4-DMA analogues with different alkoxy substituents on the 2 and 4 are synthetically very easily accessible, e.g. 2-ethoxy-4-methoxyamphetamine or 2-methoxy-4-ethoxyamphetamine. The 2-methoxy-4-somethingphenethylamine-NBOMes are known to be active compounds.

 

[Didgital]

are synthetically very easily accessible,

You're right. I failed to mention the benzaldehyde to 2,4-DMA is dirt cheap and commercially available as well. That actually does make it a bit more attractive to a clandestine chemist.

I see from wiki that 24H-NBOMe is potent 5HT2a agonist. Do you know if it's been bioassayed by humans? Also I don't know much about zebra fish, but 24H makes them panic. Do other more well known 2,5 substituted compounds do the same?