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I Like to Draw Pictures of Random Molecules

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This conspiratard blog wrote a whole bunch of speculative garbage about a related-looking compound.

tumblr_m2hnqdU6lq1rtl8vao1_1280.jpg


The blog really lays it on thick. 90% of it is bull shit backed up by one guy's assertion he's an 3l173 ch3m1z7...


I worte some slag about it on Reddit -
All known tryptamine/phenethylamine SAR models suggest that this compound is going to be much less active than the Mysterious Gentleman suggests. The racemic parent compound with no 5-methoxy or ethylthio substitutions is known in PubMed as RU-28306 but the article claims it is only equipotent to DMT at 5-HT2 (this was obviously before the eludication of the 5-HT2 subtypes). It is also totally synthetic, no such compound occurs in fish, and moreover no large-scale extraction of rare tropical fish occurs with any regularity.

7-substitution on tryptamines enhances only toxicity as far as I can see - 5,7 dihydroxytryptamine is a neurotoxin. The 7-substitution motif was discussed in some depth at Bluelight and they concluded that 7-substitution is essentially useless (7-meo drugs are generally inactive). Fuunnily enough the 5-meO 7-etS motif was mentioned there.

This smells to me like the work of someone who knows just enough SAR to be dangerously incorrect. This compound is totally novel, likely not in production, and with 90% certainty I can say it will lack the claimed "potency", even as a drug cocktail.
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The diethylamine analog you drew is probably more of a 5-ht1a agonist than anything else. I think it might be active but not very fun.
 
thenightwatch said:
ah, i guess i should have actually drawn out the molecule i was thinking of

i didn't mean replace the phenethylamine part with a tryptamine. i meant replace the other side of the molecule, the methoxyphenyl, with an indole instead. i know they made the methylenedioxyphenyl version, but did they make an indole version?

2ajthdy.jpg


25I-NIndMe?
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The 4-bromo analogue has been made!
 
^marvinsketch is pretty good and IIRC it is free.

So anyway, last month I was involved in a project developing some methodology for the direct esterification of phenols with organic acids... I won't get into synth discussion, but I know for sure cresols and catechols can be esterified under the right conditions. This got me thinking: what if one were to esterify the phenolic hydroxy group on THC with cypionic or propionic acid, with the goal of generating an ultra long-lasting derivative analogous to depo esters of steroids.

thccypionate.jpg


My question is, since this is a phenolic ester, would it be readily metabolized back to the parent hydroxy compound in a way analogous to how regular esters are metabolized? In other words, would this phenolic ester be suitable as a prodrug for THC? Is it likely to have activity of its own?

I'm not planning on trying to make this, nor would I have the means to do so even if I wanted to... but its an interesting idea, at least upon first consideration, and I'd be interested to hear any input from people who know their pharmacology. Thanks :)
 
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Roger&Me said:
^marvinsketch is pretty good and IIRC it is free.
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thank you a lot for the good hint! this is indeed bigger, more powerful and more stable than windrawchem; and much more so! :)

I am particularly impressed by its ability to recognize loads of chemicals. but there are also some strange things I noticed: e.g. it recognizes hydrogen cyanide as "cyclon"; is this some kind of weird joke? also it refers to PCP as "selma" - what the hell is that supposed to mean?
 
ungelesene_bettlek said:
thank you a lot for the good hint! this is indeed bigger, more powerful and more stable than windrawchem; and much more so! :)

I am particularly impressed by its ability to recognize loads of chemicals. but there are also some strange things I noticed: e.g. it recognizes hydrogen cyanide as "cyclon"; is this some kind of weird joke? also it refers to PCP as "selma" - what the hell is that supposed to mean?
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Zyklon B was the "trade name" for HCN used by Nazi Germany to exterminate jews during WW2
 
Pyrole-ring substitued for methylenedioxy-ring on MDxx substances?

Just an idea I came up when I was tweaked out and have always been curious about it - MDMA consists of meth with a methylenedioxy ring on it, what would the subtance be called and would it have any pharmacology if the MD ring was swapped for a pyrole ring instead, the ring on tryptamines?

Potential strogner serotonin receptor agonism? Is it even possible?

f3gwt3.png


3,4-Benzopyrollemethamphetamine, potent non-neurotoxic, serotonin releasing agent/5ht2a agonist? Or is it not active or am I just wasting time.
 
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I assume that the methylenedioxy ring on MDMA has the pharmacological significance of being highly electronegative. A pyrole ring is much more weakly electronegative, I wouldn't expect it to do much.

I'd expect it to be a not-so-great amphetamine. Perhaps similar effects-wise to 4-FA? Anyone care to weigh in on that? (4-FA releases 5-HT)

(note: "weaker" version of meth, not "tweaker" version of meth :p)

-TCM Vegas
 
This is an isomer of AMT.

A. Shulgin said:
And there are five possible chain relocation, from the normal 3-position to the 2, the 4, the 5, the 6 or the 7-positions. All five "alpha-methyltryptamine" isomers are known, but only one is known to be active in man as a CNS active material. This is the 5-isomer, 5-(2-aminopropyl)indole or 5-IT, which, at 20 milligrams orally, is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours.
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this compound depicted is 6-IT. Ifyou flopped the nitrogen around to the "bottom", it's 5-IT.
5-IT is known to be neurotoxic and generally stressful as a recreational drug, it's probably not anything worthwhile... (I think there have been deaths from 5-IT in the Nordic countries)
 
Is it known to be neurotoxic?

There have indeed been deaths from 5-IT where it has been sold as ecstasy (in scotland) or 6-APB (in sweden). The incredibly slow comeup leads to people taking more because they think it's weak when it's not at all.
 
I would put good money on it being a neurotoxin just because it's a potent monoamine releaser.
Put it this way, I don't think it's an excellent MDMA replacement.
 
I just got interested in jimscaline, but I'm not completely clear on understanding it's structure compared to mescaline.

I see that it's an indane, with the 2 rings. but does jimscaline also have 3 methoxy groups like mescaline? Or are they something different.

220px-Jimscaline.png


edit:
I guess I just found my own answer in the IUPAC.
1-(4,5,6-Trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine
 
Right, so it's not known to be neurotoxic then. I am sure it could be neurotoxic but you can probably see why I was confused.
 
Given how close the structure of 6-IT is to other known monoamine toxins (IAP, 5-IT, MDMA) I would put money on it causing 5HT depletion.
 
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