I Like to Draw Pictures of Random Molecules

[SeenSoFar]

I would be very interested in seeing the first one explored in more detail. I'd also like to see the alpha-methylated analogue.

The second one I think would not have the effect you are aiming for. Alpha-methylated n-benzyl phenethylamine compounds are inactive from my understanding. The alpha-desmethyl might have some activity, but I believe it would probably be too bulky for the SERT. Still, it would be interesting to see what effect it did have...

 

[sekio]

N-benzyl-MDA is known and inactive.

 

[crazycatman]

3,4-dichloro-ethylphenidate

Hi, I already posted a few questions on this hypothetical compound in a few other places, but apparently there isn't any info about the compound in question. So I thought ADD would be my best bet.

Anyway for quite some time I've been wondering would such a combination of 3,4-CTMP and EPH be possible to make and what kind of effect it would have. But apparently there is zero info about it online (like nobody ever even bothered synthesizing it). Since this is the most advanced part of the board regarding these things I thought I'd ask my questions here.

-has this ever been synthesised/tested?
-if not is there a particular difficulty in the synthesis that makes it problematic (not looking for instructions so hope this is fine by the rules) or has just nobody tried it yet?
-can anyone make an educated guess what the effect would be like? similar to 3,4-CTMP? to EPH? to MPH? to a long acting EPH that works at mg doses? something completely different? inactive?
-can anyone make an educated guess about it's toxicity? similar to other MPH modifications? worse? less toxic?
-could did be made by the body in the presence of alcohol the same way MPH can be turned to EPH? Or is it's structure different enough to prevent the enzyme from working?

Anything else you think about this compound and it's possible properties?

Thanks!

 

[SeenSoFar]

N-benzyl-MDA is known and inactive.

I don't believe there are any active α-alkylated n-benzyl phenethylamines, are there? I haven't heard of them if there are. If anyone knows of such a compound, I would be very interested in hearing about it.

I would also be curious to hear how β-substitution worked on N-benzylated phenethylamines. I have not heard of such compounds, but considering that the N-benzyl moiety has been said to shift the binding position relative to the N-desbenzyl parent compounds, I think it would be safe to say that the effect would be different from β-substituted N-desbenzyl phenethylamines.

Has anyone heard of such a compound? If so, has it(have they) been assayed, either in vitro or in vivo? What was the result?

 

[sekio]

move to random molecules thread

I don't believe there are any active α-alkylated n-benzyl phenethylamines, are there?

benzphetamine? or is that a meth prodrug?

technically, the N-benzyl-DOx compounds are active, just 1/10 the potency or less of the "parent" NBOMes.

But apparently there is zero info about it online (like nobody ever even bothered synthesizing it). Since this is the most advanced part of the board regarding these things I thought I'd ask my questions here.

you could also try a literature search. although if the paper describing 3,4-diCl-TMP doesn't mention the EPH analogue, there's a good chance nobody's made it, because the people doing research have a finite supply of time and money, and making all possible analogues of a compound can be a devlish task.

regarding actual kinetics/toxicity we can't say anything, only guess, until it gets tested. but given the differences between the dichloro-mph and plain mph, one would reasonably expect it to be more selective for DAT & have a longer duration of effects, due to increased lipophilicity.

i seem to recall that the "wrong" enantiomer of ethylphenidate is made in the liver, preferentially, so ethanol+methylphenidate coingestion isn't really as big of a concern as most people make it out to be.

 

[crazycatman]

Sekio, thanks for your indepth reply. I tried another more thorough search and found a few papers describing the various mph modifications including 3,4-diCl-TMP, but nothing about a 3,4-dichloro ethylphenidate (in fact most of the articles than mentioned ethylphenidate were the ones talking about your body making it in your liver if alcohol is present). I also found a thread on another board where some members speculated if 3,4-CTMP could also get transesterified in your body like mph to eph if alcohol is present. No proof of course.

As for your guess about the effects, that be nice if it were true. A longer lasting EPH. If it were also active in mg doses.... well it would make a fine RC as far as I'm concerned.

 

[babylonboy]

Dichloroethylphenidate is just not something that's going to excite the market, if you want to see it it's going to be a labour of love.

 

[sekio]

A longer lasting EPH. If it were also active in mg doses.... well it would make a fine RC as far as I'm concerned.

This is where Mother Nature throws a big ol' curve ball to us chemists... dichloro-mehylphenidate had a much higher potency, but I recall it lacked the reinforcing effects of rapid administration MPH, because it took so long to reach peak plasma concentrations (higher potency = more fat soluble = poorer absorbtion) Hoisted by its own petard as it were...

 

[SeenSoFar]

So, I was perusing some literature on methaqualone and it's analogues tonight, and it occurred to me that I had never heard of ring-closed analogues. I figured that they were an obvious and possibly interesting avenue of exploration, considering the popularity the all-mighty Quaalude enjoyed at one time.

Going from the top down, left to right, the first one is methaqualone (duh) (EDIT:The topmost nitrogen in the methaqualone structure should have a double bond connecting it to the carbon on it's right. I don't know how that slipped through...), the second and third are two possible ring closures depending on which ortho- position the methyl group belongs on (I have seen it drawn both ways), the fourth is a combination of the second and third, the fifth is the third with an added double bond to make it planar, the sixth is the fifth with an added amino group (I have seen mention of an amino group at this position increasing potency in literature), and the seventh is something that no chemwank should be without!

I have a feeling that the second would not be very potent, if active at all, since the modification of the ketone into part of a pyran ring has altered the geometry significantly. The fifth and sixth are perfectly planar, and I would be interested to know what effect this would have on things. Any and all comments would be appreciated!

 

[bloodshed344]

2(I think it's 2)-methoxy MDPEA


Analog of MDA and mescaline. What do you guys think? I know the amphetamine version is known but I couldn't find any good description of the effects.

4-methylmescaline

and just because I'm lazy, I'll copy one... cheating I know but I thought of the chemical in my head

A,N,N-TMT aka alpha-methyl DMT.

I would be happy to be the test subject for all of these chemicals, and close derivatives, and the obvious variations (amphetamine versions of the phenethylamines, 4-HO and 5-MeO versions of A,N,N-TMT)

 

[pharmakos]

first one has a mention in the PiHKAL entry for 2-methoxy-3,4-MDA, from http://www.erowid.org/library/books_online/pihkal/pihkal134.shtml

The product, 2-methoxy-3,4-methylenedioxyphenethylamine hydrochloride (2C-3a) melted at 143-145 °C. A series of subjective evaluations were made, and there are reports of marginal effects in the 40 to 120 milligram range. At 40 milligrams, perhaps the hint of a psychic energizer; at 65 milligrams, there was a pleasant mood elevation; at 80 milligrams, there was a brief paresthetic twinge noted at about the hour and a half point, and at 120 milligrams, about the same at one hour, and then nothing. The fact that there can be such a modest change of effect over a three-fold range of dosage suggests that this compound might have some merit as an anti-depressant. It would be interesting to know if it blocks serotonin reuptake!

second one has a full PiHKAL entry of its own: http://www.erowid.org/library/books_online/pihkal/pihkal052.shtml

the third one surprisingly doesn't seem to have been discussed in TiHKAL, and barely has any google hits

edit -- my google skills suck apparently. there's a metnion of a,N,N-TMT here http://www.erowid.org/library/books_online/tihkal/tihkal08.shtml

as well as a wikipedia article here: http://en.wikipedia.org/wiki/Alpha-N,N-Trimethyltryptamine

and it even has a very short bluelight thread here: http://www.bluelight.ru/vb/threads/...pha-N-N-Trimethyltryptamine-(-N-N-TMT)-Thread

 

[bloodshed344]

first one has a mention in the PiHKAL entry for 2-methoxy-3,4-MDA, from http://www.erowid.org/library/books_online/pihkal/pihkal134.shtml



second one has a full PiHKAL entry of its own: http://www.erowid.org/library/books_online/pihkal/pihkal052.shtml

the third one surprisingly doesn't seem to have been discussed in TiHKAL, and barely has any google hits

edit -- my google skills suck apparently. there's a metnion of a,N,N-TMT here http://www.erowid.org/library/books_online/tihkal/tihkal08.shtml

as well as a wikipedia article here: http://en.wikipedia.org/wiki/Alpha-N,N-Trimethyltryptamine

and it even has a very short bluelight thread here: http://www.bluelight.ru/vb/threads/...pha-N-N-Trimethyltryptamine-(-N-N-TMT)-Thread

Thanks, but I've already seen the BL thread on A,N,N-TMT but I wasn't sure if those people had even had the real thing because it's unheard of nowadays. Also the TIHKAL entry on A,N-DMT had very little info of A,N,N-TMT (it just mentioned it and that was it)

Also, DESOXY (or as I say 4-methylmescaline) seems pretty interesting, but not as good as I hope. The 4-bromo variant mentioned in the page is interesting too, I'd love to see a TFM there. Would be a magical molecule most probably.

and the last one, MMDA-3a is not what I was referring to. The one I posted was the phenethylamine version, not amphetamine. However MMDA-3a sounds amazing!
edit: Okay thanks for the clarification thenightwatch.

Thank you for the information... I hope to come up with more cool mescaline-MDA mixes. The idea fascinates me for some reason. Also I'm dying to try A,N,N-TMT!

But I should have figured most of my ideas were already thought of, haha.

 

[pharmakos]

and the last one, MMDA-3a is not what I was referring to. The one I posted was the phenethylamine version, not amphetamine. However MMDA-3a sounds amazing!

i know what you meant. the PiHKAL entry on MMDA-3a has a paragraph on the phenethylamine version (i quoted the paragraph above, note the first line "The product, 2-methoxy-3,4-methylenedioxyphenethylamine hydrochloride (2C-3a) )

 

[SeenSoFar]

Just a quick one tonight. I was messing around and figured out a compound that overlays almost 100% perfectly with Ketamine as far as 3D geometry is concerned. I made the cyclohexane ring a piperidine ring to bypass the arylcyclohexylamine analogue laws that have recently been passed in a few locations. I have not found any references regarding this substitution one way or another, so I would be very interested in knowing what effects this would have on activity. Any opinions?

Here is the model, and comparative 3D structures so people can see how it overlays!

 

[pharmakos]

very interesting. hopefully the nitrogen on the piperidine wouldn't alter activity too much... that's the only glaring difference between the 3d structures.

 

[SeenSoFar]

I almost wonder if the conversion of the cyclohexane to piperidine is even necessary... I don't know that it would even be considered an arylcyclohexylamine even with the cyclohexane intact, considering it is an indoline. Can someone with knowledge of the way the arylcyclohexylamine catch-all is written confirm if this would be considered controlled?

 

[MrPorter]

4-HO-MMT + some other effects like heroin/morphine & 4-AcO-DMT/4-HO-DMT. Was thinking of doing it with the DMT but not sure how that would work. 4 covalents (one coordinate) so N+ ion, plus a negative ion, chlorine or something? Or have a trimethyl on the Nitrogen, keep the diester as an o- and have electrostatic attraction? But yeah, just something fun I made up. Or maybe just a carbonate ion joining both?

 

[Incunabula]

Just a quick one tonight. I was messing around and figured out a compound that overlays almost 100% perfectly with Ketamine as far as 3D geometry is concerned. I made the cyclohexane ring a piperidine ring to bypass the arylcyclohexylamine analogue laws that have recently been passed in a few locations. I have not found any references regarding this substitution one way or another, so I would be very interested in knowing what effects this would have on activity. Any opinions?

Here is the model, and comparative 3D structures so people can see how it overlays!

NSFW:

I don't understand......You made a structural isomer of ketamine? and you expect it to be active?

I guess I just don't get the 3D thing...

 

[SeenSoFar]

Its not a structural isomer, the cyclohexane ring is replaced with a piperidine ring and there is an extra bond as well, with the carbon at the end of the amine chain bound to the piperidine ring to form the 5 membered ring of an indoline. There are also three less hydrogen atoms in the novel compound.

Ketamine chemical formula: C₁₃H₁₆ClNO
Novel Compound chemical formula: C₁₂H₁₃ClN₂O

It is a different molecule with a unique structure, but shares a similarity with ketamine in an important way. Imagine you could take a molecule of ketamine and a molecule of this new compound, and enlarge them to the point that they were visible with the naked eye. You would see two unique compounds with two unique structures. Imagine as well that you could superimpose one on top of the other in 3D space and see how they would overlap. You would see that these two compounds occupy almost exactly the same position in 3D space. The 3D geometry of a ligand is a very important part of its ability to bind to a particular target. The only glaring difference is the nitrogen in the cyclohexane ring, which is why I had asked if anyone had heard of this being tried before and if so, what the results were.

Sorry if I didn't explain myself clearly in my first post.

 

[ebola?]

Can someone with knowledge of the way the arylcyclohexylamine catch-all is written confirm if this would be considered controlled?

The problem is that it will ultimately be a judge who decides this, not a biochemist (or anyone working in a related field). So who knows...

VERY intriguing observation, btw...

ebola