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I Like to Draw Pictures of Random Molecules

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electrodevo said:
I had to chuckle when I encountered the kavalactone methysticin for that reason.

(I'm actually surprised how little information there is out there on kavalactones, although my guess is that structurally the isolated compounds would be rather weak in whatever action they have.)
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I have heard discussion on using the MDKavalactones as precursors for MDXX production. I seem to recall that the kavalactones are very hard to isolate and pretty unstable too which is why they seem to be relatively unexplored.
 
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gkHBHDO.png
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Is this dimethocaine inspired? Dimethocaine inspired things are a dead end.

ebola
 
Here's a long one tonight. The phenethylamine-based compounds are actually based on hard science and theories, while the tryptamines were just a funny way to fill up the rest of the page.

The phenethylamine-derived compounds are based on two methodologies. The first, as tested and theorized by Shulgin in PiHKAL, is that the heavier elements in column 16 of the periodic table can and do substitute for oxygen in phenethylamine SAR, albeit adding their own flavour along the way. The second is the observation that with PEAs, especially releasing agents, the less planar the molecule, the lower the activity. Hence why MD(M)A is beloved, while ED(M)A is for all intents and purposes inactive. After having studied the 3D structures of these and other related compounds, the conclusion that I come to is that the more planar the ring systems are, the more likely it is that the compound will be a winner. Perhaps the transporters do not have much tolerance for non-planar rings... Anyway, armed with these ideas, I have sketched up several compounds that may show promise.

The tryptamines on the other hand are just a hilarious hypothetical into heavy atom benzenes. The phosphorine is the only one that I think might theoretically be active... I also think ingesting it might have unforseen consequences on your health...

Anyway, enjoy!

8b5.png
 
The first two are actually the same compound (look at the names)- single bonds allow free rotation, so the two structures are equivalent. The sulfur/selenium/tellurium compounds would stink (literally). As for the tryptamines, your valences are all over the shop, and in general, with all these things, I find myself asking- why? Although I do understand the pleasures of noodling away some time with Chemdraw.
 
i thought the mescaline analogues with sulfurs at the 2/3/5 positions were less active than e.g. 4-thiomescaline

and yeah, the precursors would smell like satan's ass.

also, aromatic rings with phosphorous, boron and tin?! i don't think so
 
Actually, those aromatic rings are real compounds (siline, borabenzene, stannabenzene, phosphorine) they're just hideously unstable! Most of them fall to pieces under anything other than very specific conditions. Hence why I said the tryptamine-esque compounds were nowhere near serious.

As for the phenethylamine-esque compounds, I am aware of the fact that the first two compounds are identical, the original plan was to draw another compound there, so I copy/pasted the first one, made a few changes, and then got sidetracked with something else and never came back to it! By the time I noticed it was already posted and I figured I would just leave it and not say anything :P.

I do believe that potency is lost with thioether analogues of mescaline as sekio pointed out, but I was more looking for an interesting active compound, not necessarily the next NBOMe :P. Anyway, its all just a fun diversion. If I thought I was on to something serious I would be calling for custom synthesis. I just love this thread too much!

PS: Could you imagine a powerful psychedelic with a horrendous smell? Imagine the street names it could get! "God's Asshole," "Shit On My Mind," or the ever-so-obvious "Holy Shit!"
 
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another nit to pick: the dehydro-ethylenedioxy groups don't look like a stable thing to me... I think it would sooner fall apart to hydroxyacetaldehyde.
 
I'm not sure in that regard, sekio. I would not be surprised if you're right though. I trust your judgement over mine for sure!
 
PS: Could you imagine a powerful psychedelic with a horrendous smell? Imagine the street names it could get! "God's Asshole," "Shit On My Mind," or the ever-so-obvious "Holy Shit!"
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Many (most even) batches of AMT smell like shit.
 
babylonboy said:
Many (most even) batches of AMT smell like shit.
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This actually worked to my advantage recently. A batch of aMT came in and by smell alone I knew that it was not aMT. Turns out someone made a (possibly intentional) fuck-up and left me the proud owner of far more 5-MeO-DALT than I think I will ever know what to do with... Why couldn't it have been something more interesting that it got mixed up with?!
 
Jesusgreen said:
Indeed it was.

This next one's probably shown up in the thread at some point already, or at least the non ketone version:
aii4GaU.png
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I love replacing oxygens with a sulfur and I love MDMA analogs. Hard on achieved.

Some ideas I don't feel like drawing...
5-methylthioDMT
alpha-methylpsilocin
4,5-dihydroxyDMT
4-acetyl-5-methoxy-DMT
2,3,4,5,6-pentamethoxyphenethylamine
3,5-dimethoxy,4-trifluoromethylphenethylamine

and finally...
3,4 Methylenedioxy phenyl bicyclobutanamine (tcb-2 version of mdma because I dont know if the name is right)
 
bloodshed344 said:
I love replacing oxygens with a sulfur and I love MDMA analogs. Hard on achieved.

Some ideas I don't feel like drawing...
Click to expand...

5-methylthio-DMT
http://www.erowid.org/library/books_online/tihkal/tihkal46.shtml
http://en.wikipedia.org/wiki/5-MeS-DMT
http://www.bluelight.ru/vb/archive/index.php/t-588378.html?


alpha-methylpsilocin

https://en.wikipedia.org/wiki/4-HO-αMT

4,5-dihydroxyDMT
unlikely to be very good
http://www.bluelight.ru/vb/archive/index.php/t-319891.html

4-acetyl-5-methoxy-DMT
known in masturbatory biosynthetic musings
may actually be a prodrug for 4,5-diHO-Ts.. which may be toxic, see above.

2,3,4,5,6-pentamethoxyphenethylamine
given the low activity of.e.g. tetramethoxyamphetamine, i dunno.

3,5-dimethoxy,4-trifluoromethylphenethylamine
probably a winner... 2ctfm is probably also nice
 
sekio said:
5-methylthio-DMT
http://www.erowid.org/library/books_online/tihkal/tihkal46.shtml
http://en.wikipedia.org/wiki/5-MeS-DMT
http://www.bluelight.ru/vb/archive/index.php/t-588378.html?


alpha-methylpsilocin

https://en.wikipedia.org/wiki/4-HO-αMT

4,5-dihydroxyDMT
unlikely to be very good
http://www.bluelight.ru/vb/archive/index.php/t-319891.html

4-acetyl-5-methoxy-DMT
known in masturbatory biosynthetic musings
may actually be a prodrug for 4,5-diHO-Ts.. which may be toxic, see above.

2,3,4,5,6-pentamethoxyphenethylamine
given the low activity of.e.g. tetramethoxyamphetamine, i dunno.

3,5-dimethoxy,4-trifluoromethylphenethylamine
probably a winner... 2ctfm is probably also nice
Click to expand...
Thank you very much for all of that especially the info about 4,5-dihydroxy-DMT and the other. 2,3,4,5,6-tetramethoxyphenethylamine is supposed to be more potent than mescaline according to what I read but i'm not sure if I gleaned that information right. Just one thing 4-ho-amt isn't alpha-methylpsilocin. Alpha-methylpsilocin would be 4-hydroxy-a,n,n-TMT. Probably less potent than psilocin.
 
200px-Diclofenac.svg.png


I'm not suggesting this as a psychoactive. Obviously it's not (it's diclofenac).

However, what I am wondering is if anyone has ever made a phenethylamine derivative with a substitution pattern like this. I don't predict any, much less strong activity, but I don't know that it doesn't either. No one would have suspected the O-methoxybenzyl substitution would have been as potency enhancing as it is for PEA's either. It wouldn't be hard to take diclofenac and produce a phenethylamine, but I'm not well situated for that (I can throw nitro's on anything though ;)). Given that aromatic amines aren't exactly hepato-friendly, perhaps replacing the aniline NH with a simple methylene.
 
bloodshed344 said:
Thank you very much for all of that especially the info about 4,5-dihydroxy-DMT and the other. 2,3,4,5,6-tetramethoxyphenethylamine is supposed to be more potent than mescaline according to what I read but i'm not sure if I gleaned that information right. Just one thing 4-ho-amt isn't alpha-methylpsilocin. Alpha-methylpsilocin would be 4-hydroxy-a,n,n-TMT. Probably less potent than psilocin.
Click to expand...

I would be careful with 4,5-DiOH-DMT. Looks like a potential dopaminergic neurotoxin.
 
bloodshed344 said:
I love replacing oxygens with a sulfur and I love MDMA analogs. Hard on achieved.
Click to expand...


Doesn't often work out well. MPA loses to MA, 4-MTA loses to PMA (hard to believe!) 4-MTMA loses to PMMA too.

Does anyone know of a phenethylamine/tryptamine/amphetamine type drug which a sulfur-for-oxygen substitution produces a favorable result?

I'd probably have to go to depressants to find a good one.
 
What makes the amines so important, why don't we get phenethanols or tryptanols(?) ? Somehing to do with it being basic I presume.

Loved the MrMDPorLSDter molecule as well, I think the MD ring is essentially required to complete any chemwank session
 
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