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I Like to Draw Pictures of Random Molecules

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Wonder if this compound has any LSD-like activity?

Suminarole.png

Sumanirole

a D2 selective agonist (D2 agonists make rats(and humans!) incredibly horny!, is that right?


Sumanirole (PNU-95,666) is a highly selective D2 receptor full agonist, the first of its kind to be discovered.[1][2][3] It was developed for the treatment of Parkinson's disease and restless leg syndrome. While it has never been approved for medical use [4][5] it is a highly valuable tool compound for basic research to identify neurobiological mechanisms that are based on a dopamine D2-linked (vs. D1, D3, D4, and D5-linked) mechanism of action. [3]
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Ketamine:

2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one.png



Bromadol:

4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol.png



merge and melt (metabolites des-phenethyl ) DAT + OP + NMDA

Ketamadol (2P-K): Buddha Haus
4-(2-chlorophenyl)-4-(methylamino)-1-(2-phenylethyl)piperidin-3-one.png
 
Don't have a chemdraw app I can upload from but have MDMA analogues with a C-C double bond ever been considered? [h=2] [(1Z)-1-(2H-1,3-benzodioxol-5-yl)prop-1-en-2-yl](methyl)amine and [(1E)-1-(2H-1,3-benzodioxol-5-yl)prop-1-en-2-yl](methyl)amine would be the two isomers. Would the double bond be too easily substituted?[/h]
 
The double bond will naturally migrate to the adjacent N and form an imine (R-N=R'). Imines break apart when touched by H2O. Saliva and gastric juices are wet.
 
You'll end up with methylamine and 3,4-methylenedioxyphenyl-2-propanone, neither of which is gone get you high.
 
Dresden said:
The double bond will naturally migrate to the adjacent N and form an imine (R-N=R'). Imines break apart when touched by H2O. Saliva and gastric juices are wet.
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Not necessarily. As I said, the double bond is conjugated with the aromatic system, which gives the enamine tautomer stability. Analogous to how in aniline the enamine is the more stable form as opposed to the imine. However, that doesn't necessarily give it stability against water, that is true.
 
Isn't the aromatic system already stabilizing the methylenedioxy ring?

Plus finally as you say: even if the equilibrium is a bit more favorable to the enamine, doesn't it become irrelevant when the ketimine hydrolysis is a much less reversible reaction of another order of magnitude?

Even if the details are not agreed on, it seems it's agreed this is not a fruitful direction.
 
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Solipsis said:
Isn't the aromatic system already stabilizing the methylenedioxy ring?
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That doesn't mean the double bond cannot be stabilized as well, that's not how it works. On the contrary, the bigger the conjugated system, the more stable it is generally.

Solipsis said:
Plus finally as you say: even if the equilibrium is a bit more favorable to the enamine, doesn't it become irrelevant when the ketimine hydrolysis is a much less reversible reaction of another order of magnitude?
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Yes, that is what I meant by it still probably not being very stable in water. Even if the enamine is the favored form, it may still be in a significant enough equilibrium with the imine, which would in turn be hydrolyzed. However, without empirical data I cannot really say whether it would render the compound useless or not. I mean, benzos have imine moieties too, which can be prone to hydrolysis, yet they're stable enough in vivo, are they not?
 
Are there any psychoactive drugs that have lithium substituted in where a hydrogen or some other group would normally be? I'm imagining something like 2C-Lithium. Is this even possible?
 
perpetualdawn said:
Are there any psychoactive drugs that have lithium substituted in where a hydrogen or some other group would normally be? I'm imagining something like 2C-Lithium. Is this even possible?
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No, because you'll end up with an incredibly reactive molecule which will alkylate ... many things in the body.
 
Solipsis said:
oh yeah, thought for a moment it was electron withdrawing..

@benzo

http://www.auburn.edu/~deruija/GABA_ Benzodiazepines2002.pdf

page 7

Poor solubility precludes degradation? , otherwise I cannot explain why benzo's retain activity orally if the stomach is very acidic and hydrolytic reactions render it inactive irreversibly.
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Actually, I've been thinking about it and I would probably explain benzo's stability by the fact that the imine is cyclic and actually the hydrolytic reaction is not irreversible (the molecule stays intact and the reactants don't diffuse away from each other). So, considering that intramolecular reactions typically occur very rapidly, because molecules like that change conformations very rapidly and the amino moiety has a lot more chance of "hitting" the carbonyl. As opposed to it being a reaction between two separate molecules by way of diffusion. Well, that's just my thoughts. Then again, the amine would probably be protonated quite strongly, even at blood pH, which renders it quite a useless nucleophile.

Anyway, sorry for off-topic posts.

Bagseed said:
yeah organometallics, and especially R-Li is not a good idea in a drug molecule
wink.gif
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Unless you like to live life on the edge ;-)
 
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