Why did Nichols give up on making dimethylaziridine analogues of LSD?

[aced126]

They could've provided more good information on the binding to the protein.


In acidic conditions, N-acetylaziridine decomposes. The N gets protonated (its lone pair has more s character to compensate for ring strain, hence why also N-acetyl aziridine is not planar as it is less conjugated with the C=O bond.

However in basic conditions it seems that deprotonation of the nitrogen after the acylation has occured gives a stable N-methyl-aziridine.

Am I missing something?

 

[aced126]

Oh and of course, it worked with azetidine, from which one of the 3 isomers was more potent than LSD in DD studies.

 

[Weltmeister]

Theres actually a video on youtube where nicols talks about this. Ill try to find but it might take some time.

If i remember correctly the compounds werent stable enough and thus they disregarded them.

 

[Solipsis]

https://www.erowid.org/general/newsletter/erowid_newsletter23.pdf

page 6