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I Like to Draw Pictures of Random Molecules

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aced126 said:
(5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-acetyl-17-phenylethylmorphinan-6-one

Can't figure out how to put the image of this on opsin onto here.
Click to expand...

Try using simpler nomenclature. Stereochemical letters and numbering are not required. I would start by seeing if opsin recognizes "morphinan" first. If not, nomeclature for that one could be a real b*tch. However, it would just be so much clearer and more precise to see your structure.

If that still doesn't work, try explaining your molecule's name with things like, "It's like hydromorphone but with an N-phenylethyl instead of an N-methyl," or whatnot. Just my advice.
 
Also, on the subject of lysergamides, I found this pretty good paper (skip to page 55) where the researchers synthesised a load of n-6 substituted lysergamides and compared activity. Isopropyl substitution on n-6 leads to half the potency of LSD and Butyl substitution leads to a tenth of the potency.

They also try to understand why the diethyl substitution on the amide N makes the molecule so potent, and so synthesised some dimethylaziridinyl diasteromers and actually found that one of them showed 1.5 times potency of LSD.

http://archives.drugabuse.gov/pdf/monographs/146.pdf
 
It's like oxymorphone, with an acetyl group on the 3 oxygen (where methyl group for codeine normally goes) and the nitrogen is substituted with a phenylethyl substitution.

Just realised though that the acetyl group would make the molecule less potent because even though it improves BBB permeability, the phenolic group is important in the binding region of mu...
 
You're so close now! Just go to those webpages and copy the URL then type
with no spaces either time. Voila! You will have posted your images successfully.
 
aced126 said:
Also, on the subject of lysergamides, I found this pretty good paper (skip to page 55) where the researchers synthesised a load of n-6 substituted lysergamides and compared activity. Isopropyl substitution on n-6 leads to half the potency of LSD and Butyl substitution leads to a tenth of the potency.

They also try to understand why the diethyl substitution on the amide N makes the molecule so potent, and so synthesised some dimethylaziridinyl diasteromers and actually found that one of them showed 1.5 times potency of LSD.

http://archives.drugabuse.gov/pdf/monographs/146.pdf
Click to expand...

"There's methyl and ethyl, but butyl is futile."--ancient drug designer maxim.

As for the dimethylazidirine LSD ("LSZ"), I've tried it, and it was a huge disappointment.
 
aced126 said:
Also, on the subject of lysergamides, I found this pretty good paper (skip to page 55) where the researchers synthesised a load of n-6 substituted lysergamides and compared activity. Isopropyl substitution on n-6 leads to half the potency of LSD and Butyl substitution leads to a tenth of the potency.

They also try to understand why the diethyl substitution on the amide N makes the molecule so potent, and so synthesised some dimethylaziridinyl diasteromers and actually found that one of them showed 1.5 times potency of LSD.

http://archives.drugabuse.gov/pdf/monographs/146.pdf
Click to expand...

Ah, yeah. I didn't know Nichols had made the Isopropyl sub. I guess it's too obvious to not have been done. Anyway, there you go, "MAL-LAD" would most certainly be less potent than the n-6 isopropyl. I came to think of CYP-LAD, it might be even closer to that in bulkyness.

Interesting paper that one, I will have to read it when I have time.

And about LSZ, yeah, it's the only lysergamide that ever gave me a bodyload. Horrible stuff. Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is also supposed to be more potent than LSD proper. I really hope we will see that one, as well as LSP, available some time in the future.
 
Yes, ya'll are right. I do remember N-MeO-MDA (#111 from PiHKAL); however, it was inactive IIRC.

N-methoxy-2-amino-1-(3,4-methylenedioxyphenyl)propane.png


Still, for some reason R-N-O-R' doesn't seem to show up much, and I don't think it was what Brother Rico was talking about anyway.

Do you mean N,N-diethyl-2-butyl-lysergamide? This:

N,N-diethyl-2-butyl-lysergamide.png
 
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Oh, ok.

Here are another two:

N,N-diethyl-12-methoxylysergamide.png


and

N,N-diethyl-12-chlorolysergamide.png


The first one looks incredibly mind blowing to me.
 
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What do you mean? This can't be made into a Bentley compound cos the double bond has been hydrogenated. I'd expect this compound to be reasonably potent however, but not in the range of some of the potent Bentley compounds.
 
Simple yet interesting. Guessing the methoxy FG at 4 position would reduce potency compared to a hydroxy at that position, and similarly a hydroxy at 5 would reduce potency in comparison to a methoxy. These assumptions are based on comparisons between psilocin and 4-meo-dmt, and bufotenin and 5-meo-dmt. Nevertheless you never know...
 
aced126 said:
What do you mean? This can't be made into a Bentley compound cos the double bond has been hydrogenated. I'd expect this compound to be reasonably potent however, but not in the range of some of the potent Bentley compounds.
Click to expand...

Oh sorry, nvm. It was posted betwixt so many of posts of lysergic type drugs that I thought it was a serotonin agonist, it looked close to an opioid just 'cause that was all that it was. ;p

So my question would then be: might there be an LSD-analog that's a morphinan, then, I suppose is what my curiousity was aiming at? Would it be closer to the NMDAR antagonist enantiomer of the structure or the opioid if it could be done?

EDIT:
iaBFp.jpg


Unrelated to the topic at hand, a Glutethimide / Pethidine intermediate of my own devising; a sedative hypnotic and opioid / slight DRI.
 
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