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I Like to Draw Pictures of Random Molecules

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I have a hunch this one would be better due to greater ring activation afforded by the added methoxy group:

1-(3-methoxy-4-pentylphenyl)-2-methylaminopropane.png


However, I was completely wrong about 3-MeO-MA, which is almost devoid of psychoactivity (I actually tried it.).

1-(3-methoxyphenyl)-2-methylaminopropane.png


However, this one is known to be active:

1-(3-methoxy-4-methylphenyl)-2-aminopropane.png


* * *

We can dance if we want it. We can go to a place they'll never find. Because your friends don't dance, and if they don't dance, well they're no friends of mine. As long as we have music, everything will work out fine.

* * *

This

1-(3-methoxy-4-pentylphenyl)-2-aminopropane.png


is probably a safer bet, as N-methylation makes these compounds weaker and smoother.

And I seriously doubt that

1-(4-pentylphenyl)-2-methylaminopropane.png


is a reuptake inhibitor.

This

1-(4-pentylphenyl)-1-oxo-2-(1-pyrrolidinyl)pentane.png


might be one though.

* * *

Bad seed from bad sperm.
Herb got my wig fried like a bad perm.
 
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Indole. But tryptamines are a subset of indoles. That is, all tryptamines are indoles, but not all indoles are tryptamines. To illustrate, here are the basic hydrocarbon skeletons of each:

tryptamine.png


Tryptamine

indole.png


Indole (JENKEM)

My compound

1-(1-piperidinyl)-1-(indole-3-yl)cyclohexane.png


has its N in the wrong place to technically be called a tryptamine but is definitely an indole and possibly a wicked good trip!!!
 
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Is it possible to see the source stating 4-MA is a metabolite of mephedrone. I simply cannot see how this could happen. Reducing the alpha ketone would make the molecule more lipophilic and harder to excrete.
 
I'm pretty sure the benzylic keto of mephedrone is simply reduced to the corresponding alcohol but not any further for that C. In other words, I don't think 4-MA is a metabolite of mephedrone. If it were, then (pseudo)ephedrine ought to be metabolized to methamphetamine!

Of course, not all metabolic reactions of drugs are sensical or necessarily make the subject less high. For example, about 10% of an oral dose of MDMA gets converted to MDA, which is even more potent per mg than MDMA in most respects.
 
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SKL said:
Boy, that sent me a bit down the rabbit-hole, and I'm a bit intrigued. I knew the soundbite, and it's available on Wiki, but trying to dig deeper, I can find next to nothing about amfepentorex and it's pharmacology via the usual venues, but haven't found much.

There's not a lot of useful information I could readily find about it, except for the basics, it was marketed in France as an appetite suppressant, etc., save a few references that I think I'd have to track down in print (fortunately I have access to a wonderful public library here in the City that stocks 1960s era Chimica Therapeutica, Vol. 2, Pg. 260, 196, if that will help at all ....)

Now, this is a pretty interesting chemical, actually. Question being, how far can we take single ring substituted amphetamines? A lot of us will be familiar with 4-methyl-AMP, which by all accounts wasn't very impressive, and is more serotonergic than anything else, I've actually seen some contradictory reports as to whether it's a serotonin/dopamine releaser or an S(N?)DRI. The EMCDDA has a pretty solid report about it. This of course, is without the N-methyl. 4-methyl-MA is a metabolite of mephedrone, and has some role in it's activity I figure, but sounds kind of toxic. So I guess the question is, what do we get by the N-methyl and particularly elongating the chain at the 4 position? If I can only hazard a guess I think this molecule might have some significant serotonergic activity which might well have to do with it's utility as an appetite suppressant, a la locaserin (which see, is an also interesting molecule ...), but evidently retains some dopaminergic/amphetamine type actions as well. I've really had some trouble locating specific information about this molecule, it seems rather forgotten, although the time I've spent is limited. My interest is a bit piqued though. More later maybe. I'd love to know any sort of subjective account of this experience or of course more details about it's pharmacology/SAR (which as far as my limited knowledge goes suggests it may be a bit serotonergic, maybe more towards being a reuptake inhibitor?)

(1R)-8-chloro-1-methyl-2%2C3%2C4%2C5-tetrahydro-1H-3-benzazepine.png

not related but interesting in it's own right
this is primarily serotonergic
and a controlled substance in the USA
allegedly has some psychedelic-ish effects in high doses
but who would really want to?
Click to expand...

I don't think it would have much SERT action if my reasoning is correct.

http://onlinelibrary.wiley.com/doi/1....201300013/pdf
http://www.ncbi.nlm.nih.gov/pubmed/2623014

The active site of SERT seems to be very tight. The second link shows that ethylidenedioxymethamphetamine (methyl group on methylene carbon) is half the potency MDMA. Isopropylidene derivative (2 methyl groups on methylene carbon) has no activity at all. I don't think a long chain like that is going to fit.
 
All metabolic reactions are "sensical" in that they all ease excretion of the new metabolite. That doesn't necessarily mean the metabolite might have more or less action at its target.
 
"All" can be a tricky word when taken literally. Of course, I can't think of any counter-examples.
 
Dresden said:
has its N in the wrong place to technically be called a tryptamine but is definitely an indole and possibly a wicked good trip!!!
Click to expand...
ah I overlooked the missing carbon in there. do you think it would be active / psychedelic with a CH2 group squeezed in between the indole and the cyclohexane? (or between N and cyclohexane) ^^
 
Possibly. I was trying to propose a PCP like molecule with tryptamine like psychoactive properties.

The Infamous PCP:

1-phenyl-1-(1-piperidinyl)cyclohexane.png


What I proposed:

1-(1-piperidinyl)-1-(indole-3-yl)cyclohexane.png


What you proposed:

1-(1-piperidinylmethyl)-1-(indole-3-yl)cyclohexane.png


Now that is, arguably, sort of a tryptamine. I know this one is supposed to be a doosey:

1-(1-pyrrolidinyl)-2-(indole-3-yl)ethane.png


And you won't see me volunteering to take this:

1-(indole-3-yl)-2-(1-pyrrolidinyl)-1-oxopentane.png


But maybe that's because I hate AMT, which other people love, and which kills people with some regularity.

AMT:

1-(indole-3-yl)-2-aminopropane.png


5-MeO-AMT is even more nefarious:

1-(5-methoxyindole-3-yl)-2-aminopropane.png


But, for some reason, I would like to try 4-OH-AMT:

1-(4-hydroxyindole-3-yl)-2-aminopropane.png


And this little potentially stoning spunion (a spunion is a spun youngin'):

1-oxo-1-(1-pentyl-4-hydroxyindole-3-yl)-2-aminopropane.png


But would rather opt for this:

1-oxo-1-(4-hydroxy-1-pentylindole-3-yl)-2-dimethylaminoethane.png


And no, I am not on

1-phenyl-2-methylaminopropane.png


today. Only the highly legal

1-cyclohexyl-2-methylaminopropane.png


propylhexedrine!
 
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start with cocaine (my favorite for some reason, not my DOC but in QSAR I can't get it out of my mind)

IyAyF.jpg


Back-bridge the nitrogen on the tropane + bridge the carbmethoxy and remove the oxygens to where the bridge on the nitrogen splits off, and make that styrene into a triple bond instead of double, and...
 
It's still a 17 year old boy on a thumbprint of LSD. Here's another one I want to try.

3-dimethylaminoethyl-4-hydroxy-6-pentylindole.png


Sasha left virtually wide open the field of ring substituted tryptamines.
 
Let's try the same with phenethylamines:

Adding 3'-aza to the cylcohexyl ring:

1-phenyl(3-azacyclohexyl)amine

1-phenyl%283-azacyclohexyl%29amine.png


With 2-keto: 1-phenyl(2-keto-3-azacyclohexyl)amine

1-phenyl%282-keto-3-azacyclohexyl%29amine.png


Now let's have some fun:

Amphetamine versions instead:

1-phenyl(2-methyl-3-azacyclohexyl)amine
1-phenyl(2,3-dimethyl-3-azacyclohexyl)amine


1-phenyl%282-methyl-3-azacyclohexyl%29amine.png
1-phenyl%282-methyl-3-methyl-3-azacyclohexyl%29amine.png




Norbane mostruosities in the cyclohexyl ring:

6-phenyl-2-azabicyclo[2.2.1]heptan-6-amine
2-methyl-6-phenyl-2-azabicyclo[2.2.1]heptan-6-amine

6-phenyl-2-azabicyclo%5B2.2.1%5Dheptan-6-amine.png
2-methyl-6-phenyl-2-azabicyclo%5B2.2.1%5Dheptan-6-amine.png




Now some "psychedelics"

2C-C / DOC version (Chlorine just because ketamine, bromine and alkylated versions welcome)

1-(4-chloro-2,5-dimethoxyphenyl)-(3-azacyclohexyl)amine / 1-(4-chloro-2,5-dimethoxyphenyl)-(2-keto-3-azacyclohexyl)amine / 1-(4-chloro-2,5-dimethoxyphenyl)-(2-methyl-3-azacyclohexyl)amine



1-%284-chloro-2%2C5-dimethoxyphenyl%29-%283-azacyclohexyl%29amine.png
1-%284-chloro-2%2C5-dimethoxyphenyl%29-%282-keto-3-azacyclohexyl%29amine.png
1-%284-chloro-2%2C5-dimethoxyphenyl%29-%282-methyl-3-azacyclohexyl%29amine.png



(Now just add a subtitutent to the amine as you like)
 
Here are some interesting examples:

3-MeO-PCP / 2C-B Hybrid

3-(4-bromo-2,5-dimethoxyphenyl)-3-(piperidin-1-yl)piperidine


3-%284-bromo-2%2C5-dimethoxyphenyl%29-3-%28piperidin-1-yl%29piperidine.png


Let's switch around the methoxies and make something closer to ketamine:


3-(2-chloro-3,4-dimethoxyphenyl)-3-(methylamino)piperidin-2-one

3-(2-chloro-3%2C4-dimethoxyphenyl)-3-(methylamino)piperidin-2-one.png


We can also switch the keto group around:

3-(2-chloro-3,4-dimethoxyphenyl)-3-(methylamino)piperidin-4-one

3-(2-chloro-3%2C4-dimethoxyphenyl)-3-(methylamino)piperidin-4-one.png


Here's the 2-FMA norborane / PCP one

6-(2-fluorophenyl)-2-methyl-6-(piperidin-1-yl)-2-azabicyclo[2.2.1]heptane

6-(2-fluorophenyl)-2-methyl-6-(piperidin-1-yl)-2-azabicyclo%5B2.2.1%5Dheptane.png


The possibilities are pretty much endless!
 
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