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EXP-561 : Any suggestions on its receational value and toxicity issues?

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/navarone/

Bluelighter
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This was a tough one to find on Wiki due to the scarcity of links to the page.

220px-EXPfivesixone.png

EXP-561
http://en.wikipedia.org/wiki/EXP-561

It's an intriguing article plus the molecule looks so geometrically cool!! =D
I'm wondering about how does this substance compare to cocaine. The molecule looks much more metabolically stable than cocaine.
Any info or guesse on its recreational value and related toxicity?
 
Why does the wiki article claim it to be an analogue of amphetamine?

No matter how I look at it, I can't see the structural resemblance, other than both have an aryl and an amine.
 
One of the reasons for the structure-activity paradox is that a molecule is 4-D, not 3-D. A molecule is a heterogenous superposition of all its relative rotations.

structural, skeletal and 3D formulas of neopentane:

100px-Neopentane-2D.png
100px-Neopentane-2D-skeletal.png
150px-Neopentane-3D-balls.png



double-rotation of a 4D tetrahedron:

5-cell.gif
 
seep said:
One of the reasons for the structure-activity paradox is that a molecule is 4-D, not 3-D. A molecule is a heterogenous superposition of all its relative rotations.

structural, skeletal and 3D formulas of neopentane:

100px-Neopentane-2D.png
100px-Neopentane-2D-skeletal.png
150px-Neopentane-3D-balls.png



double-rotation of a 4D tetrahedron:

5-cell.gif
Click to expand...

i have no idea how that is even possible. is it just that the motion of carbon atoms in a molecule like neopentane can be more easily visualized as moving like the vertexes of a 4d tetrahedron when the tetrahedron is rotated in 4d space but projected in 3d? sorry if this confuses anyone.

does anyone have any links for further reading on this topic?
 
thenightwatch said:
i have no idea how that is even possible. is it just that the motion of carbon atoms in a molecule like neopentane can be more easily visualized as moving like the vertexes of a 4d tetrahedron when the tetrahedron is rotated in 4d space but projected in 3d?
Click to expand...

It's just my half-assed attempt at a Gedankenexperiment. I can visualize it better that way, but the question is can it be modeled better that way?

Neopentane is a simple template for a thought experiment cuz its intramolecular movement is pretty-much limited to rotation of the terminal methyls). The bond angles stay pretty fixed. It has one conformer.

Consider the molecule's movement in a fluid of some turbulence. The molecule is rotating along its center of mass (the nucleus of the quaternary carbon). Since the ambient fluid has turbulence, the molecule's angular and translational velocity are changing at changing rates (i.e. there is variable acceleration). There is sufficient flux in the fluid to demonstrate that the molecule as a whole is rotating very rapidly and very erratically (relative to a rigid reference point outside the system).

Assume one of its hydrogens is a deuterium. You can't predict where that deuterium will be at any one time (see above). So then, even if you know the exact coordinates of the molecule, you can't know the position of the individual atoms. They are essentially delocalized over the globular (hyperspherical) range of the spinning, drifting molecule. But the pentachoron (hyperpyramid) is a better dynamic model because since neopentane has one conformer, the delocalization isn't spherical but pentachoronical (hyperpyramidal).

Or something.

This becomes non-trivial when you take into account the principles of Brownian movement, conformation-activity relationship and bioisosterism.
 
How is it not an analogue of amphetamine? It's significantly more complex, but it's still an analogue. Look at it in 3D, overlays decently well with amphetamine.

going any route, there's an additional methylene group between the aryl ring and the amine, but and the alpha-methyl is constrained back into the ring, but it's hardly a stretch to call it an analogue.
 
Hammilton said:
How is it not an analogue of amphetamine? It's significantly more complex, but it's still an analogue. Look at it in 3D, overlays decently well with amphetamine.
Click to expand...
No, it doesn't. The nitrogens are about 3.2 Å away from each other in a quick overlay with MM2-minimized models. Furthermore does EXP-561 not contain a phenethylamine-substructure, but rather a phenbutylamine.



The analogy is solely on the pharmacological level, but not on the chemical one.


Peace! - Murphy
 
^Maybe. Didn't look really closely at the pharmacological part though :\

Edit: Ah yeah, Wiki tells the answer. You're right!
 
Some abstract from PAN institute of pharmacology. It actually negates pharmacological resemblance to amphetamine. It's the first one in Google after typing EXP-561... I don't think it would make a good antidepressant.
 
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