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I Like to Draw Pictures of Random Molecules

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Anyone had any first-hand experience with this?

ATOMOXETINE.jpg
 
JacksinPA said:
I'd be interested in evaluating an azido (Nsub3) group in place of the main ring system chlorine. I've seen nitro. Another EWG that is of interest to me is CFsub3. I'm sure they've all been made & evaluated. Too potent or toxic?
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Organic azides do not tend to be the most stable compounds, to the point where inorganic azide salts and low-molecular weight organic azides tend to be shock-sensitive explosives.... not to mention azide salts as well as several organic azides being fairly toxic.

Trifluoromethyl groups shouldn't pose any such problem. I know of trifluoromethyl analogues of nordazepam (triflunordazepam) and clobazam (triflubazam), but these never saw market adoption, probably because you'd only see a modest increase in potency at best, while requiring a harder to obtain precursor.

Interestingly, benzos containing a trifluoroethyl group on the 1-nitrogen atom did see pharmaceutical use. One of these is halazepam (N-fluoroethyl-nordazepam), which was quickly withdrawn from the US market again because it didn't sell, however. The other and much more interesting one is quazepam. Quazepam and its metabolite 2-oxoquazepam apparently exhibit much higher selectivity for the sleep-inducing subunits of the GABA receptor than other benzos, similar to the z-drugs zolpidem and zaleplon.
 
This analog of caffeine is said to be 100 times more active at both the A1& A2 receptors.

During WWII the Germans needed coffee to keep their war industry going 24 hours/day. Due to the Allied embargo on coffee beans, ersatz coffee was made using synthetic caffeine. I've seen the synthesis method in an Allied intelligence report & it is not simple, beginning with relatively complex raw materials like ethyl cyanoacetate. A significant amount of German war productivity went into making synthetic coffee, as did the production of their popular soft drink, FANTA. In the case of FANTA, coloring & flavoring came from industrial byproducts because importation of the original drink syrup from Coca-Cola was also blocked..

1-3-di-n-propyl-7-propargylxanthine.jpg
 
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I still hate terminal alkyne, too toxic in most of thr cases not limited to this cafe-analog.

Regarding atomoxetine, it gives me alot of sweat and anxiety, and removes every traces of my appetite.
Me not touching it again!
 
Hodor said:
Organic azides do not tend to be the most stable compounds, to the point where inorganic azide salts and low-molecular weight organic azides tend to be shock-sensitive explosives.... not to mention azide salts as well as several organic azides being fairly toxic.

Trifluoromethyl groups shouldn't pose any such problem. I know of trifluoromethyl analogues of nordazepam (triflunordazepam) and clobazam (triflubazam), but these never saw market adoption, probably because you'd only see a modest increase in potency at best, while requiring a harder to obtain precursor.

Interestingly, benzos containing a trifluoroethyl group on the 1-nitrogen atom did see pharmaceutical use. One of these is halazepam (N-fluoroethyl-nordazepam), which was quickly withdrawn from the US market again because it didn't sell, however. The other and much more interesting one is quazepam. Quazepam and its metabolite 2-oxoquazepam apparently exhibit much higher selectivity for the sleep-inducing subunits of the GABA receptor than other benzos, similar to the z-drugs zolpidem and zaleplon.
Click to expand...

I agree with your comments on quazepam (DORAL) regards inducing sleep.

You got the linear nomenclature for halazepam wrong. See attached graphic. Intermediates derived from 2,2,2-trifluoroethanol, are commonly available on the market. The correct nomenclature is N-(2,2,2-trifluoroethyl)-.

HALAZEPAM-QUAZEPAM-FLETAZEPAM.jpg
 
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Anyone had any first-hand experience with [atomoxetine]?
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I once took 80mg and it made me feel like I'd been hit by a truck while simultaneously having the flu. In retrospect it's probably a massive overdose but I was young and dumb...
 
sekio said:
I once took 80mg and it made me feel like I'd been hit by a truck while simultaneously having the flu. In retrospect it's probably a massive overdose but I was young and dumb...
Click to expand...

40 mg is the STARTING dose for ADHD. Assuming you don't have ADHD, it may have acted like someone dropping a case of beer on your brain.
 
I don't have this paper so the details of this synthesis are not clear but the final tricyclic compound is said to be a powerful CNS stimulant:

2-hydrazino-5-8-methanoquinazoline.jpg


Interesting from an SAR perspective. But not exactly home lab chemistry.
 
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Be cautious when contemplating even small lab-scale ozonlysis. I worked in a lab where we made tens of kilos of a perfume ingredient using an industrial-scale ozonator (>$19K) & had to run the ozonolysis in ice-cold methylene chloride in 22-liter flasks. I don't think Walmart sells either CH2Cl2 or elemicin.

Because of both ambient heat & the heat of reaction, keeping those big flasks at around 0 deg C was a lot of work. The product passed & I got paid
 
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JacksinPA,

I already have elemicin. But as watched as I am [think permanent Saturday Night Live actor status], I am not *about* to do anything funny with it.

And I did 100mg 5-MAPB once. Hard to describe altered state of consciousness that ended in mild delirium--I desperately called my dad around 11 pm although he was just one room away. Will not voluntarily repeat.

AMP
 
Thanks for the feedback of 5-MAPB. I just crossed it off my bucket list of things to try before I croak.
 
Non-benzodiazepine full Bz receptor agonist(s)

I only have access to the first page of the full journal article but this caught my eye:

6-benzyloxy-4-methoxymethyl-b-carboline-3-carboxylic-acid-et.jpg


For some reason I could not recover the full article through Sci-Pub.

Interesting from the SAR POV. Wonder what other analogs they produced & evaluated. Not lab-scale chemistry in any event.
 
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According to the book QD 1 A355 no. 45 p. 117,

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


MP-809

Is "particularly effective in the treatment of neurotic depressions" and "is only a weak MAOI."
 
Methyl huh? Interesting!
I am now interested in ethyl analog at the same position then, similar electron density at aromatic ring positions, and also the approximately same size as an MeO-
 
1. i finally can overlay them a bit already with benzos! Thanks jacksin! Albeit you should flip ru32514 by 180 degree, and flip front to back before stacking!
Not looking so well in 2 D tho, but in 3D they do!
 
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